Glutamic acid.docx

8/9/2019 Glutamic acid.docx

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Glutamic acid

Glutamic acid

IUPAC name [hide]

Glutamic acid

Other names [hide]

2-Aminopentanedioic acid2-Aminoglutaric acid

IdentifiersCAS number 6 !-6"-2

ChemSpider "#

U$II 6 %&O"I "S

'(GG )*+,+

Ch( I C.( I/ 02,!

Ch(1 % C.(1 %2!6,0#

&mol-,) images Image S1I%(S

[sho ]InChI

[sho ]Properties

1olecular 3ormula C". # $O +1olar mass +!4 , g mol 5

Appearance hite cr stalline po der )ensit 4+6* 72* 8C9

1elting point ## 8C decomp4

Solubilit in ater 046+ g:l 72" 8C9 [ ]

Solubilit *4***,"g: **g ethanol 2" degC [2]

Supplementary data pageStructure and n;


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properties=hermod namicdata

Phase beha>iour Solid; li?uid; gas

Spectral data U@; I ; $1 ; 1S 7>eri3 9 7 hat is/ : B9

( cept here noted other ise; data are gi>en 3or materials intheir standard state 7at 2" 8C; ** DPa9In3obo re3erences

Glutamic acid 7abbre>iated as Glu or E 9 is one o3 the 2*-22 proteinogenic amino acids ; andits codons are GAA and GAG4 It is a non- essential amino acid 4 =he carbo late anions andsalts o3 glutamic acid are Dno n as glutamates 4 In neuroscience ; glutamate is an importantneurotransmitter that pla s a De role in long-term potentiation and is important 3or learningand memor 4[,]

Chemistry

=he side chain carbo lic acid 3unctional group has p' a o3 +4 and e ists in its negati>elcharged deprotonated carbo late 3orm at p.s greater than +4 there3ore it is also negati>elcharged at ph siological p. ranging 3rom !4," to !4+"4

History

1ain article/ Glutamic acid 73la>or9

Although the occur naturall in man 3oods; the 3la>or contributions made b glutamic acidand other amino acids ere onl scienti3icall identi3ied earl in the t entieth centur 4 =hesubstance as disco>ered and identi3ied in the ear 066; b the German chemist 'arl.einrich %eopold itthausen ho treated heat gluten 73or hich it as named9 ith sul3uricacid 4[+] In #*! &apanese researcher 'iDunae IDeda o3 the =oD o Imperial Uni>ersit identi3ied bro n cr stals le3t behind a3ter the e>aporation o3 a large amount o3 Dombu brothas glutamic acid4 =hese cr stals; hen tasted; reproduced the ine33able but undeniable 3la>or

he detected in man 3oods; most especiall in sea eed4 Pro3essor IDeda termed this 3la>orumami 4 .e then patented a method o3 mass-producing a cr stalline salt o3 glutamic acid;monosodium glutamate 4["] [6]

Biosynthesis

Reactants Products Enzymes

Glutamine E . 2O F Glu E $. , G%S; G%S2

$AcGlu E . 2O F Glu E Acetate 7unDno n9

-Detoglutarate E $A)P . E $. +E F Glu E $A)P E E . 2O G%U) ; G%U)2 [!]

-Detoglutarate E -amino acid F Glu E -Deto acid transaminase

-P rroline-"-carbo late E $A) E E . 2O F Glu E $A). A%).+A

$-3ormimino-%-glutamate E H. + F Glu E "-3ormimino-H. + H=C)
http://en.wikipedia.org/wiki/Glutamic_acid_(data_page)#Structure_and_propertieshttp://en.wikipedia.org/wiki/Glutamic_acid_(data_page)#Thermodynamic_propertieshttp://en.wikipedia.org/wiki/Glutamic_acid_(data_page)#Thermodynamic_propertieshttp://en.wikipedia.org/wiki/Glutamic_acid_(data_page)#Spectral_datahttp://en.wikipedia.org/wiki/UV/VIS_spectroscopyhttp://en.wikipedia.org/wiki/Infrared_spectroscopyhttp://en.wikipedia.org/wiki/Infrared_spectroscopyhttp://en.wikipedia.org/wiki/NMR_spectroscopyhttp://en.wikipedia.org/wiki/Mass_spectrometryhttp://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=476993405&page2=Glutamic+acidhttp://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=476993405&page2=Glutamic+acidhttp://en.wikipedia.org/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validationhttp://en.wikipedia.org/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validationhttp://en.wikipedia.org/wiki/Standard_statehttp://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox#Referenceshttp://en.wikipedia.org/wiki/Proteinogenic_amino_acidhttp://en.wikipedia.org/wiki/Proteinogenic_amino_acidhttp://en.wikipedia.org/wiki/Codonshttp://en.wikipedia.org/wiki/Essential_amino_acidhttp://en.wikipedia.org/wiki/Carboxylate_anionhttp://en.wikipedia.org/wiki/Salt_(chemistry)http://en.wikipedia.org/wiki/Neurosciencehttp://en.wikipedia.org/wiki/Neurosciencehttp://en.wikipedia.org/wiki/Neurotransmitterhttp://en.wikipedia.org/wiki/Neurotransmitterhttp://en.wikipedia.org/wiki/Long-term_potentiationhttp://en.wikipedia.org/wiki/Glutamic_acid#cite_note-twsNovK11-2http://en.wikipedia.org/wiki/Glutamic_acid#cite_note-twsNovK11-2http://en.wikipedia.org/wiki/Side_chainhttp://en.wikipedia.org/wiki/Carboxylic_acidhttp://en.wikipedia.org/wiki/Functional_grouphttp://en.wikipedia.org/wiki/Functional_grouphttp://en.wikipedia.org/wiki/Functional_grouphttp://en.wikipedia.org/wiki/Acid_dissociation_constanthttp://en.wikipedia.org/wiki/Acid_dissociation_constanthttp://en.wikipedia.org/wiki/Negatively_chargedhttp://en.wikipedia.org/wiki/Negatively_chargedhttp://en.wikipedia.org/wiki/Deprotonationhttp://en.wikipedia.org/wiki/Carboxylatehttp://en.wikipedia.org/wiki/Carboxylatehttp://en.wikipedia.org/wiki/Physiological_pHhttp://en.wikipedia.org/wiki/Physiological_pHhttp://en.wikipedia.org/wiki/Glutamic_acid_(flavor)http://en.wikipedia.org/wiki/Glutenhttp://en.wikipedia.org/wiki/Glutenhttp://en.wikipedia.org/wiki/Sulfuric_acidhttp://en.wikipedia.org/wiki/Sulfuric_acidhttp://en.wikipedia.org/wiki/Glutamic_acid#cite_note-3http://en.wikipedia.org/wiki/Kikunae_Ikedahttp://en.wikipedia.org/wiki/Tokyo_Imperial_Universityhttp://en.wikipedia.org/wiki/Kombuhttp://en.wikipedia.org/wiki/Umamihttp://en.wikipedia.org/wiki/Monosodium_glutamatehttp://en.wikipedia.org/wiki/Glutamic_acid#cite_note-guardian-4http://en.wikipedia.org/wiki/Glutamic_acid#cite_note-5http://en.wikipedia.org/wiki/Reactantshttp://en.wikipedia.org/wiki/Product_(chemistry)http://en.wikipedia.org/wiki/Enzymeshttp://en.wikipedia.org/wiki/Glutaminehttp://en.wikipedia.org/wiki/Glutaminehttp://en.wikipedia.org/wiki/Waterhttp://en.wikipedia.org/wiki/Waterhttp://en.wikipedia.org/wiki/Waterhttp://en.wikipedia.org/wiki/Ammoniahttp://en.wikipedia.org/wiki/Ammoniahttp://en.wikipedia.org/wiki/Protein:GLShttp://en.wikipedia.org/wiki/Protein:GLS2http://en.wikipedia.org/wiki/Protein:GLS2http://en.wikipedia.org/wiki/N_acetylglutamic_acidhttp://en.wikipedia.org/wiki/N_acetylglutamic_acidhttp://en.wikipedia.org/wiki/Waterhttp://en.wikipedia.org/wiki/Waterhttp://en.wikipedia.org/wiki/Waterhttp://en.wikipedia.org/wiki/Acetatehttp://en.wikipedia.org/wiki/Alpha-Ketoglutaric_acidhttp://en.wikipedia.org/wiki/NADPhttp://en.wikipedia.org/wiki/NADPhttp://en.wikipedia.org/wiki/Protein:GLUD1http://en.wikipedia.org/wiki/Protein:GLUD2http://en.wikipedia.org/wiki/Protein:GLUD2http://en.wikipedia.org/wiki/Glutamic_acid#cite_note-springerlink-6http://en.wikipedia.org/wiki/Alpha-Ketoglutaric_acidhttp://en.wikipedia.org/wiki/Amino_acidhttp://en.wikipedia.org/wiki/Keto_acidhttp://en.wikipedia.org/wiki/Transaminasehttp://en.wikipedia.org/wiki/1-Pyrroline-5-carboxylatehttp://en.wikipedia.org/wiki/1-Pyrroline-5-carboxylatehttp://en.wikipedia.org/wiki/Nicotinamide_adenine_dinucleotidehttp://en.wikipedia.org/wiki/Nicotinamide_adenine_dinucleotidehttp://en.wikipedia.org/wiki/Protein:ALDH4A1http://en.wikipedia.org/wiki/N-formimino-L-glutamatehttp://en.wikipedia.org/wiki/N-formimino-L-glutamatehttp://en.wikipedia.org/wiki/Folic_acidhttp://en.wikipedia.org/wiki/Folic_acidhttp://en.wikipedia.org/wiki/Folic_acidhttp://en.wikipedia.org/wiki/Folic_acidhttp://en.wikipedia.org/wiki/Protein:FTCDhttp://en.wikipedia.org/wiki/Glutamic_acid_(data_page)#Structure_and_propertieshttp://en.wikipedia.org/wiki/Glutamic_acid_(data_page)#Thermodynamic_propertieshttp://en.wikipedia.org/wiki/Glutamic_acid_(data_page)#Thermodynamic_propertieshttp://en.wikipedia.org/wiki/Glutamic_acid_(data_page)#Spectral_datahttp://en.wikipedia.org/wiki/UV/VIS_spectroscopyhttp://en.wikipedia.org/wiki/Infrared_spectroscopyhttp://en.wikipedia.org/wiki/NMR_spectroscopyhttp://en.wikipedia.org/wiki/Mass_spectrometryhttp://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=476993405&page2=Glutamic+acidhttp://en.wikipedia.org/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validationhttp://en.wikipedia.org/wiki/Standard_statehttp://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox#Referenceshttp://en.wikipedia.org/wiki/Proteinogenic_amino_acidhttp://en.wikipedia.org/wiki/Codonshttp://en.wikipedia.org/wiki/Essential_amino_acidhttp://en.wikipedia.org/wiki/Carboxylate_anionhttp://en.wikipedia.org/wiki/Salt_(chemistry)http://en.wikipedia.org/wiki/Neurosciencehttp://en.wikipedia.org/wiki/Neurotransmitterhttp://en.wikipedia.org/wiki/Long-term_potentiationhttp://en.wikipedia.org/wiki/Glutamic_acid#cite_note-twsNovK11-2http://en.wikipedia.org/wiki/Side_chainhttp://en.wikipedia.org/wiki/Carboxylic_acidhttp://en.wikipedia.org/wiki/Functional_grouphttp://en.wikipedia.org/wiki/Acid_dissociation_constanthttp://en.wikipedia.org/wiki/Negatively_chargedhttp://en.wikipedia.org/wiki/Negatively_chargedhttp://en.wikipedia.org/wiki/Deprotonationhttp://en.wikipedia.org/wiki/Carboxylatehttp://en.wikipedia.org/wiki/Physiological_pHhttp://en.wikipedia.org/wiki/Glutamic_acid_(flavor)http://en.wikipedia.org/wiki/Glutenhttp://en.wikipedia.org/wiki/Sulfuric_acidhttp://en.wikipedia.org/wiki/Sulfuric_acidhttp://en.wikipedia.org/wiki/Glutamic_acid#cite_note-3http://en.wikipedia.org/wiki/Kikunae_Ikedahttp://en.wikipedia.org/wiki/Tokyo_Imperial_Universityhttp://en.wikipedia.org/wiki/Kombuhttp://en.wikipedia.org/wiki/Umamihttp://en.wikipedia.org/wiki/Monosodium_glutamatehttp://en.wikipedia.org/wiki/Glutamic_acid#cite_note-guardian-4http://en.wikipedia.org/wiki/Glutamic_acid#cite_note-5http://en.wikipedia.org/wiki/Reactantshttp://en.wikipedia.org/wiki/Product_(chemistry)http://en.wikipedia.org/wiki/Enzymeshttp://en.wikipedia.org/wiki/Glutaminehttp://en.wikipedia.org/wiki/Waterhttp://en.wikipedia.org/wiki/Ammoniahttp://en.wikipedia.org/wiki/Protein:GLShttp://en.wikipedia.org/wiki/Protein:GLS2http://en.wikipedia.org/wiki/N_acetylglutamic_acidhttp://en.wikipedia.org/wiki/Waterhttp://en.wikipedia.org/wiki/Acetatehttp://en.wikipedia.org/wiki/Alpha-Ketoglutaric_acidhttp://en.wikipedia.org/wiki/NADPhttp://en.wikipedia.org/wiki/NADPhttp://en.wikipedia.org/wiki/Protein:GLUD1http://en.wikipedia.org/wiki/Protein:GLUD2http://en.wikipedia.org/wiki/Glutamic_acid#cite_note-springerlink-6http://en.wikipedia.org/wiki/Alpha-Ketoglutaric_acidhttp://en.wikipedia.org/wiki/Amino_acidhttp://en.wikipedia.org/wiki/Keto_acidhttp://en.wikipedia.org/wiki/Transaminasehttp://en.wikipedia.org/wiki/1-Pyrroline-5-carboxylatehttp://en.wikipedia.org/wiki/Nicotinamide_adenine_dinucleotidehttp://en.wikipedia.org/wiki/Protein:ALDH4A1http://en.wikipedia.org/wiki/N-formimino-L-glutamatehttp://en.wikipedia.org/wiki/Folic_acidhttp://en.wikipedia.org/wiki/Folic_acidhttp://en.wikipedia.org/wiki/Protein:FTCD


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Function and uses

Meta olism

Glutamate is a De compound in cellular metabolism 4 In humans; dietar proteins are broDendo n b digestion into amino acids ; hich ser>e as metabolic 3uel 3or other 3unctional rolesin the bod 4 A De process in amino acid degradation is transamination ; in hich the aminogroup o3 an amino acid is trans3erred to an -Detoacid; t picall catal sed b a transaminase 4=he reaction can be generalised as such/

-amino acid E 2- -Detoacid - -Detoacid E 2-amino acid

A >er common -Deto acid is -Detoglutarate; an intermediate in the citric acid c cle 4=ransamination o3 -Detoglutarate gi>es glutamate4 =he resulting -Detoacid product is o3tena use3ul one as ell; hich can contribute as 3uel or as a substrate 3or 3urther metabolism

processes4 ( amples are as 3ollo s/

Alanine E -Detoglutarate p ru>ate E glutamateAspartate E -Detoglutarate o aloacetate E glutamate

oth p ru>ate and o aloacetate are De components o3 cellular metabolism; contributing assubstrates or intermediates in 3undamental processes such as gl col sis ; gluconeogenesis ; andthe citric acid c cle 4

Glutamate also pla s an important role in the bod s disposal o3 e cess or aste nitrogen 4Glutamate undergoes deamination ; an o idati>e reaction catal sed b glutamatedeh drogenase ;[!] as 3ollo s/

glutamate E . 2O E $A)P E F -Detoglutarate E $A)P. E $. , E . E

Ammonia 7as ammonium 9 is then e creted predominantl as urea ; s nthesised in the li>er 4=ransamination can; thus; be linDed to deamination; e33ecti>el allo ing nitrogen 3rom theamine groups o3 amino acids to be remo>ed; >ia glutamate as an intermediate; and 3inalle creted 3rom the bod in the 3orm o3 urea4

!eurotransmitter

Glutamate is the most abundant e citator neurotransmitter in the >ertebrate ner>ous s stem 4[0] At chemical s napses ; glutamate is stored in >esicles 4 $er>e impulses trigger release o3glutamate 3rom the pre-s naptic cell4 In the opposing post-s naptic cell; glutamate receptors ; such as the $1)A receptor ; bind glutamate and are acti>ated4 ecause o3 its role in s naptic

plasticit ; glutamate is in>ol>ed in cogniti>e 3unctions liDe learning and memor in the brain4[#] =he 3orm o3 plasticit Dno n as long-term potentiation taDes place at glutamatergics napses in the hippocampus ; neocorte ; and other parts o3 the brain4 Glutamate orDs notonl as a point-to-point transmitter but also through spill-o>er s naptic crosstalD bet eens napses in hich summation o3 glutamate released 3rom a neighboring s napse createse tras naptic signaling: >olume transmission 4[ *]
http://en.wikipedia.org/wiki/Metabolismhttp://en.wikipedia.org/wiki/Metabolismhttp://en.wikipedia.org/wiki/Proteinshttp://en.wikipedia.org/wiki/Amino_acidshttp://en.wikipedia.org/wiki/Transaminationhttp://en.wikipedia.org/wiki/Transaminasehttp://en.wikipedia.org/wiki/Citric_acid_cyclehttp://en.wikipedia.org/wiki/Alaninehttp://en.wikipedia.org/wiki/Pyruvatehttp://en.wikipedia.org/wiki/Aspartatehttp://en.wikipedia.org/wiki/Oxaloacetatehttp://en.wikipedia.org/wiki/Glycolysishttp://en.wikipedia.org/wiki/Gluconeogenesishttp://en.wikipedia.org/wiki/Gluconeogenesishttp://en.wikipedia.org/wiki/Citric_acid_cyclehttp://en.wikipedia.org/wiki/Nitrogenhttp://en.wikipedia.org/wiki/Deaminationhttp://en.wikipedia.org/wiki/Glutamate_dehydrogenasehttp://en.wikipedia.org/wiki/Glutamate_dehydrogenasehttp://en.wikipedia.org/wiki/Glutamic_acid#cite_note-springerlink-6http://en.wikipedia.org/wiki/Nicotinamide_adenine_dinucleotide_phosphatehttp://en.wikipedia.org/wiki/Nicotinamide_adenine_dinucleotide_phosphatehttp://en.wikipedia.org/wiki/Ammoniumhttp://en.wikipedia.org/wiki/Ureahttp://en.wikipedia.org/wiki/Liverhttp://en.wikipedia.org/wiki/Neurotransmitterhttp://en.wikipedia.org/wiki/Neurotransmitterhttp://en.wikipedia.org/wiki/Nervous_systemhttp://en.wikipedia.org/wiki/Glutamic_acid#cite_note-pmid10736372-7http://en.wikipedia.org/wiki/Synapseshttp://en.wikipedia.org/wiki/Synapseshttp://en.wikipedia.org/wiki/Synaptic_vesiclehttp://en.wikipedia.org/wiki/Nerve_impulseshttp://en.wikipedia.org/wiki/Nerve_impulseshttp://en.wikipedia.org/wiki/Glutamate_receptorshttp://en.wikipedia.org/wiki/Glutamate_receptorshttp://en.wikipedia.org/wiki/NMDA_receptorhttp://en.wikipedia.org/wiki/Synaptic_plasticityhttp://en.wikipedia.org/wiki/Synaptic_plasticityhttp://en.wikipedia.org/wiki/Learninghttp://en.wikipedia.org/wiki/Learninghttp://en.wikipedia.org/wiki/Memoryhttp://en.wikipedia.org/wiki/Memoryhttp://en.wikipedia.org/wiki/Glutamic_acid#cite_note-8http://en.wikipedia.org/wiki/Long-term_potentiationhttp://en.wikipedia.org/wiki/Long-term_potentiationhttp://en.wikipedia.org/wiki/Hippocampushttp://en.wikipedia.org/wiki/Neocortexhttp://en.wikipedia.org/wiki/Volume_transmissionhttp://en.wikipedia.org/wiki/Glutamic_acid#cite_note-9http://en.wikipedia.org/wiki/Metabolismhttp://en.wikipedia.org/wiki/Proteinshttp://en.wikipedia.org/wiki/Amino_acidshttp://en.wikipedia.org/wiki/Transaminationhttp://en.wikipedia.org/wiki/Transaminasehttp://en.wikipedia.org/wiki/Citric_acid_cyclehttp://en.wikipedia.org/wiki/Alaninehttp://en.wikipedia.org/wiki/Pyruvatehttp://en.wikipedia.org/wiki/Aspartatehttp://en.wikipedia.org/wiki/Oxaloacetatehttp://en.wikipedia.org/wiki/Glycolysishttp://en.wikipedia.org/wiki/Gluconeogenesishttp://en.wikipedia.org/wiki/Citric_acid_cyclehttp://en.wikipedia.org/wiki/Nitrogenhttp://en.wikipedia.org/wiki/Deaminationhttp://en.wikipedia.org/wiki/Glutamate_dehydrogenasehttp://en.wikipedia.org/wiki/Glutamate_dehydrogenasehttp://en.wikipedia.org/wiki/Glutamic_acid#cite_note-springerlink-6http://en.wikipedia.org/wiki/Nicotinamide_adenine_dinucleotide_phosphatehttp://en.wikipedia.org/wiki/Nicotinamide_adenine_dinucleotide_phosphatehttp://en.wikipedia.org/wiki/Ammoniumhttp://en.wikipedia.org/wiki/Ureahttp://en.wikipedia.org/wiki/Liverhttp://en.wikipedia.org/wiki/Neurotransmitterhttp://en.wikipedia.org/wiki/Nervous_systemhttp://en.wikipedia.org/wiki/Glutamic_acid#cite_note-pmid10736372-7http://en.wikipedia.org/wiki/Synapseshttp://en.wikipedia.org/wiki/Synaptic_vesiclehttp://en.wikipedia.org/wiki/Nerve_impulseshttp://en.wikipedia.org/wiki/Glutamate_receptorshttp://en.wikipedia.org/wiki/NMDA_receptorhttp://en.wikipedia.org/wiki/Synaptic_plasticityhttp://en.wikipedia.org/wiki/Synaptic_plasticityhttp://en.wikipedia.org/wiki/Learninghttp://en.wikipedia.org/wiki/Memoryhttp://en.wikipedia.org/wiki/Glutamic_acid#cite_note-8http://en.wikipedia.org/wiki/Long-term_potentiationhttp://en.wikipedia.org/wiki/Hippocampushttp://en.wikipedia.org/wiki/Neocortexhttp://en.wikipedia.org/wiki/Volume_transmissionhttp://en.wikipedia.org/wiki/Glutamic_acid#cite_note-9


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Brain nonsynaptic glutamatergic signaling circuits

( tracellular glutamate in Drosophila brains has been 3ound to regulate posts napticglutamate receptor clustering; >ia a process in>ol>ing receptor desensitiKation4 [2*] A genee pressed in glial cells acti>el transports glutamate into the e tracellular space ;[2*] hile; inthe nucleus accumbens -stimulating group II metabotropic glutamate receptors; this gene as3ound to reduce e tracellular glutamate le>els 4[2 ] =his raises the possibilit that thise tracellular glutamate pla s an Mendocrine-liDeM role as part o3 a larger homeostatic s stem4

G"B" precursor

Glutamate also ser>es as the precursor 3or the s nthesis o3 the inhibitor GA A in GA A-ergic neurons4 =his reaction is catal Ked b glutamate decarbo lase 7GA)9; hich is mostabundant in the cerebellum and pancreas 4

Sti33-man s ndrome is a neurologic disorder caused b anti-GA) antibodies; leading to adecrease in GA A s nthesis and; there3ore; impaired motor 3unction such as muscle sti33nessand spasm4 Since the pancreas is also abundant 3or the enK me GA); a direct immunologicaldestruction occurs in the pancreas and the patients ill ha>e diabetes mellitus4

Fla#or enhancer

1ain article/ Glutamic acid 73la>or9

Glutamic acid; being a constituent o3 protein; is present in e>er 3ood that contains protein; but it can onl be tasted hen it is present in an unbound 3orm4 Signi3icant amounts o3 3ree

glutamic acid are present in a ide >ariet o3 3oods; including cheese and so sauce ; and isresponsible 3or umami ; one o3 the 3i>e basic tastes o3 the human sense o3 taste 4 Glutamic acidis o3ten used as a 3ood additi>e and 3la>our enhancer in the 3orm o3 its sodium salt monosodium glutamate 71SG94

!utrient

All meats; poultr ; 3ish; eggs; dair products; and Dombu are e cellent sources o3 glutamicacid4 Some protein-rich plant 3oods also ser>e as sources4 =hirt to ,"N o3 the protein inheat is glutamic acid4 $inet -3i>e percent o3 the dietar glutamate is metaboliKed bintestinal cells in a 3irst pass 4[22]

Plant gro$th

Au igro is a plant gro th preparation that contains ,*N glutamic acid4

!MR Spectroscopy

In recent ears; there has been much research into the use o3 )Cs in $1 spectroscop 4 Aglutamic acid deri>ati>e; pol - -benK l-%-glutamate 7P %G9; is o3ten used as an alignmentmedium to control the scale o3 the dipolar interactions obser>ed4 [2,]
http://en.wikipedia.org/wiki/Drosophilahttp://en.wikipedia.org/wiki/Drosophilahttp://en.wikipedia.org/wiki/Glutamic_acid#cite_note-augustin-19http://en.wikipedia.org/wiki/Glial_cellhttp://en.wikipedia.org/wiki/Extracellular_spacehttp://en.wikipedia.org/wiki/Glutamic_acid#cite_note-augustin-19http://en.wikipedia.org/wiki/Glutamic_acid#cite_note-augustin-19http://en.wikipedia.org/wiki/Nucleus_accumbenshttp://en.wikipedia.org/wiki/Glutamic_acid#cite_note-20http://en.wikipedia.org/wiki/Glutamic_acid#cite_note-20http://en.wikipedia.org/wiki/Glutamic_acid#cite_note-20http://en.wikipedia.org/wiki/GABAhttp://en.wikipedia.org/wiki/Glutamate_decarboxylasehttp://en.wikipedia.org/wiki/Cerebellumhttp://en.wikipedia.org/wiki/Cerebellumhttp://en.wikipedia.org/wiki/Pancreashttp://en.wikipedia.org/wiki/Stiff-man_syndromehttp://en.wikipedia.org/wiki/Glutamic_acid_(flavor)http://en.wikipedia.org/wiki/Cheesehttp://en.wikipedia.org/wiki/Cheesehttp://en.wikipedia.org/wiki/Soy_saucehttp://en.wikipedia.org/wiki/Soy_saucehttp://en.wikipedia.org/wiki/Umamihttp://en.wikipedia.org/wiki/Basic_tastehttp://en.wikipedia.org/wiki/Tastehttp://en.wikipedia.org/wiki/Tastehttp://en.wikipedia.org/wiki/Food_additivehttp://en.wikipedia.org/wiki/Flavour_enhancerhttp://en.wikipedia.org/wiki/Sodiumhttp://en.wikipedia.org/wiki/Sodiumhttp://en.wikipedia.org/wiki/Salthttp://en.wikipedia.org/wiki/Monosodium_glutamatehttp://en.wikipedia.org/wiki/Kombuhttp://en.wikipedia.org/wiki/Kombuhttp://en.wikipedia.org/wiki/Glutamic_acid#cite_note-21http://en.wikipedia.org/wiki/Glutamic_acid#cite_note-21http://en.wikipedia.org/wiki/Auxigrohttp://en.wikipedia.org/wiki/Residual_dipolar_couplinghttp://en.wikipedia.org/wiki/Nuclear_magnetic_resonance_spectroscopyhttp://en.wikipedia.org/w/index.php?title=Poly-%CE%B3-benzyl-L-glutamate&action=edit&redlink=1http://en.wikipedia.org/w/index.php?title=Poly-%CE%B3-benzyl-L-glutamate&action=edit&redlink=1http://en.wikipedia.org/wiki/Glutamic_acid#cite_note-22http://en.wikipedia.org/wiki/Drosophilahttp://en.wikipedia.org/wiki/Glutamic_acid#cite_note-augustin-19http://en.wikipedia.org/wiki/Glial_cellhttp://en.wikipedia.org/wiki/Extracellular_spacehttp://en.wikipedia.org/wiki/Glutamic_acid#cite_note-augustin-19http://en.wikipedia.org/wiki/Nucleus_accumbenshttp://en.wikipedia.org/wiki/Glutamic_acid#cite_note-20http://en.wikipedia.org/wiki/GABAhttp://en.wikipedia.org/wiki/Glutamate_decarboxylasehttp://en.wikipedia.org/wiki/Cerebellumhttp://en.wikipedia.org/wiki/Pancreashttp://en.wikipedia.org/wiki/Stiff-man_syndromehttp://en.wikipedia.org/wiki/Glutamic_acid_(flavor)http://en.wikipedia.org/wiki/Cheesehttp://en.wikipedia.org/wiki/Soy_saucehttp://en.wikipedia.org/wiki/Umamihttp://en.wikipedia.org/wiki/Basic_tastehttp://en.wikipedia.org/wiki/Tastehttp://en.wikipedia.org/wiki/Food_additivehttp://en.wikipedia.org/wiki/Flavour_enhancerhttp://en.wikipedia.org/wiki/Sodiumhttp://en.wikipedia.org/wiki/Salthttp://en.wikipedia.org/wiki/Monosodium_glutamatehttp://en.wikipedia.org/wiki/Kombuhttp://en.wikipedia.org/wiki/Glutamic_acid#cite_note-21http://en.wikipedia.org/wiki/Auxigrohttp://en.wikipedia.org/wiki/Residual_dipolar_couplinghttp://en.wikipedia.org/wiki/Nuclear_magnetic_resonance_spectroscopyhttp://en.wikipedia.org/w/index.php?title=Poly-%CE%B3-benzyl-L-glutamate&action=edit&redlink=1http://en.wikipedia.org/wiki/Glutamic_acid#cite_note-22


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Production

China-based Hu3eng Group %imited is the largest producer o3 glutamic acid in the orld; ithcapacit increasing to ,**;*** tons at the end o3 2**6 3rom 0*;*** tons during 2**6;

putting them at 2"N ,*N o3 the Chinese marDet4 1eihua is the second-largest Chinese producer4 =ogether; the top-3i>e producers ha>e roughl "*N share in China4 Chinese demandis roughl 4 million tons per ear; hile global demand; including China; is 4! million tons

per ear4

Pharmacology

=he drug phenc clidine 7more commonl Dno n as PCP9 antagoniKes glutamic acid non-competiti>el at the $1)A receptor4 Hor the same reasons; sub-anaesthetic doses o3Detamine ha>e strong dissociati>e and hallucinogenic e33ects4 Glutamate does not easil passthe blood brain barrier ; but; instead; is transported b a high-a33init transport s stem4 [2+] Itcan also be con>erted into glutamine 4

See also

'ainic acid

)isodium glutamate

1onosodium glutamate

References

4 % http/::haKard4com:msds:m3:baDer:baDer:3iles:g,#!*4htm

24 % http/::booDs4google4ch:booDsBidQ teiA U+6SRC pgQPA " lpgQPA" d?QmethionineEsolubilit EinEethanol sourceQbl otsQ.K.ueOPPo sigQ'J1T )$gJS>G Cdd()#l3a (h'R hlQen saQT eiQ2-26=-bV'-mT*RLt,I2ACA redirWescQ X>Qonepage ?QmethionineN2*solubilit N2*inN2*ethanol 3Q3alse

,4 Y a b c obert SapolsD 72**"94 M iolog and .uman eha>ior/ =he $eurological Origins o3 Indi>idualit ; 2nd editionM4 The Teaching Company 4 Msee pages # and 2* o3 Guide ooDM

+4 % 4.4A4 Plimmer 7 # 29 [ #*0]4 4.4A4 Plimmer H4G4 .opDins4 ed4 Thechemical composition of the proteins 4 1onographs on biochemistr 4 Part I& "nalysis 72nd ed494 %ondon/ %ongmans; Green and Co44 p4 +4 etrie>ed &une ,; 2* 24

"4 % enton; Ale 72**"-*!- *94 MI3 1SG is so bad 3or ou; h doesn te>er one in Asia ha>e a headacheBM 4 The Guardian 4 etrie>ed 2**0- -2 4
http://en.wikipedia.org/wiki/Fufeng_Grouphttp://en.wikipedia.org/wiki/Phencyclidinehttp://en.wikipedia.org/wiki/Receptor_antagonisthttp://en.wikipedia.org/wiki/Ketaminehttp://en.wikipedia.org/wiki/Blood_brain_barrierhttp://en.wikipedia.org/wiki/Glutamic_acid#cite_note-23http://en.wikipedia.org/wiki/Glutamic_acid#cite_note-23http://en.wikipedia.org/wiki/Glutaminehttp://en.wikipedia.org/wiki/Glutaminehttp://en.wikipedia.org/wiki/Kainic_acidhttp://en.wikipedia.org/wiki/Disodium_glutamatehttp://en.wikipedia.org/wiki/Monosodium_glutamatehttp://en.wikipedia.org/wiki/Glutamic_acid#cite_ref-0http://hazard.com/msds/mf/baker/baker/files/g3970.htmhttp://en.wikipedia.org/wiki/Glutamic_acid#cite_ref-1http://books.google.ch/books?id=xteiARU46SQC&pg=PA15&lpg=PA15&dq=methionine+solubility+in+ethanol&source=bl&ots=HzHueOPPoB&sig=KjMXxDNgjSvG1CddED9lfaYEhKQ&hl=en&sa=X&ei=2-26T-bZK-mX0QWt3I2ACA&redir_esc=y#v=onepage&q=methionine%20solubility%20in%20ethanol&f=falsehttp://books.google.ch/books?id=xteiARU46SQC&pg=PA15&lpg=PA15&dq=methionine+solubility+in+ethanol&source=bl&ots=HzHueOPPoB&sig=KjMXxDNgjSvG1CddED9lfaYEhKQ&hl=en&sa=X&ei=2-26T-bZK-mX0QWt3I2ACA&redir_esc=y#v=onepage&q=methionine%20solubility%20in%20ethanol&f=falsehttp://books.google.ch/books?id=xteiARU46SQC&pg=PA15&lpg=PA15&dq=methionine+solubility+in+ethanol&source=bl&ots=HzHueOPPoB&sig=KjMXxDNgjSvG1CddED9lfaYEhKQ&hl=en&sa=X&ei=2-26T-bZK-mX0QWt3I2ACA&redir_esc=y#v=onepage&q=methionine%20solubility%20in%20ethanol&f=falsehttp://books.google.ch/books?id=xteiARU46SQC&pg=PA15&lpg=PA15&dq=methionine+solubility+in+ethanol&source=bl&ots=HzHueOPPoB&sig=KjMXxDNgjSvG1CddED9lfaYEhKQ&hl=en&sa=X&ei=2-26T-bZK-mX0QWt3I2ACA&redir_esc=y#v=onepage&q=methionine%20solubility%20in%20ethanol&f=falsehttp://books.google.ch/books?id=xteiARU46SQC&pg=PA15&lpg=PA15&dq=methionine+solubility+in+ethanol&source=bl&ots=HzHueOPPoB&sig=KjMXxDNgjSvG1CddED9lfaYEhKQ&hl=en&sa=X&ei=2-26T-bZK-mX0QWt3I2ACA&redir_esc=y#v=onepage&q=methionine%20solubility%20in%20ethanol&f=falsehttp://en.wikipedia.org/wiki/Glutamic_acid#cite_ref-twsNovK11_2-0http://en.wikipedia.org/wiki/Glutamic_acid#cite_ref-twsNovK11_2-0http://en.wikipedia.org/wiki/Glutamic_acid#cite_ref-twsNovK11_2-1http://en.wikipedia.org/wiki/Glutamic_acid#cite_ref-twsNovK11_2-2http://en.wikipedia.org/wiki/Glutamic_acid#cite_ref-3http://books.google.com/?id=7JM8AAAAIAAJ&pg=PA114http://books.google.com/?id=7JM8AAAAIAAJ&pg=PA114http://en.wikipedia.org/wiki/Glutamic_acid#cite_ref-guardian_4-0http://observer.guardian.co.uk/foodmonthly/story/0,,1522368,00.htmlhttp://observer.guardian.co.uk/foodmonthly/story/0,,1522368,00.htmlhttp://en.wikipedia.org/wiki/The_Guardianhttp://en.wikipedia.org/wiki/The_Guardianhttp://en.wikipedia.org/wiki/Fufeng_Grouphttp://en.wikipedia.org/wiki/Phencyclidinehttp://en.wikipedia.org/wiki/Receptor_antagonisthttp://en.wikipedia.org/wiki/Ketaminehttp://en.wikipedia.org/wiki/Blood_brain_barrierhttp://en.wikipedia.org/wiki/Glutamic_acid#cite_note-23http://en.wikipedia.org/wiki/Glutaminehttp://en.wikipedia.org/wiki/Kainic_acidhttp://en.wikipedia.org/wiki/Disodium_glutamatehttp://en.wikipedia.org/wiki/Monosodium_glutamatehttp://en.wikipedia.org/wiki/Glutamic_acid#cite_ref-0http://hazard.com/msds/mf/baker/baker/files/g3970.htmhttp://en.wikipedia.org/wiki/Glutamic_acid#cite_ref-1http://books.google.ch/books?id=xteiARU46SQC&pg=PA15&lpg=PA15&dq=methionine+solubility+in+ethanol&source=bl&ots=HzHueOPPoB&sig=KjMXxDNgjSvG1CddED9lfaYEhKQ&hl=en&sa=X&ei=2-26T-bZK-mX0QWt3I2ACA&redir_esc=y#v=onepage&q=methionine%20solubility%20in%20ethanol&f=falsehttp://books.google.ch/books?id=xteiARU46SQC&pg=PA15&lpg=PA15&dq=methionine+solubility+in+ethanol&source=bl&ots=HzHueOPPoB&sig=KjMXxDNgjSvG1CddED9lfaYEhKQ&hl=en&sa=X&ei=2-26T-bZK-mX0QWt3I2ACA&redir_esc=y#v=onepage&q=methionine%20solubility%20in%20ethanol&f=falsehttp://books.google.ch/books?id=xteiARU46SQC&pg=PA15&lpg=PA15&dq=methionine+solubility+in+ethanol&source=bl&ots=HzHueOPPoB&sig=KjMXxDNgjSvG1CddED9lfaYEhKQ&hl=en&sa=X&ei=2-26T-bZK-mX0QWt3I2ACA&redir_esc=y#v=onepage&q=methionine%20solubility%20in%20ethanol&f=falsehttp://en.wikipedia.org/wiki/Glutamic_acid#cite_ref-twsNovK11_2-0http://en.wikipedia.org/wiki/Glutamic_acid#cite_ref-twsNovK11_2-1http://en.wikipedia.org/wiki/Glutamic_acid#cite_ref-twsNovK11_2-2http://en.wikipedia.org/wiki/Glutamic_acid#cite_ref-3http://books.google.com/?id=7JM8AAAAIAAJ&pg=PA114http://books.google.com/?id=7JM8AAAAIAAJ&pg=PA114http://en.wikipedia.org/wiki/Glutamic_acid#cite_ref-guardian_4-0http://observer.guardian.co.uk/foodmonthly/story/0,,1522368,00.htmlhttp://observer.guardian.co.uk/foodmonthly/story/0,,1522368,00.htmlhttp://en.wikipedia.org/wiki/The_Guardian


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64 % M'iDunae IDeda Sodium GlutamateM 4 &apan Patent O33ice4 2**2- *-*!4etrie>ed 2**0- -2 4

!4 Y a b Grabo sDa; A4Z $o icDi; 14Z ' inta; &4 72* 94 MGlutamatedeh drogenase o3 the germinating triticale seeds/ Gene e pression; acti>it

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04 % 1eldrum; 4 S4 72***94 MGlutamate as a neurotransmitter in the brain/e>ie o3 ph siolog and patholog M4 The Journal of nutrition (') 7+S Suppl9/**!S * "S4 P1I) *!,6,!2 4 edit

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*4 % ODubo; 4Z SeDi a; .4Z $amiDi; S4Z SaDamoto; .4Z Iinuma; S4Z amasaDi; 14ZLatanabe; 14Z .irose; '4 et al4 72* *94 MImaging e tras naptic glutamate d namics inthe brainM4 Proceedings of the National Academy of Sciences ()* 7 +9/ 6"264)OI / *4 *!,:pnas4*# , "+ *! 4edit

4 % Shigeri; 4Z Seal; 4 P4Z Shimamoto; '4 72**+94 M1olecular pharmacolog o3glutamate transporters; (AA=s and @G%U=sM4 Brain Research Re ie!s +, 7,9/ 2"* 26"4 )OI / *4 * 6:J4brainresre>42**+4*+4**+ 4 P1I) "2 *,*! 4 edit

24 % 1ane>; .4Z Ha>aron; 14Z Guidotti; A4Z Costa; (4 7 #0#94 M)ela ed increase

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,4 % . nd; 14Z Scott; .4 %4Z )odd; P4 4 72**+94 MGlutamate-mediatede citoto icit and neurodegeneration in AlKheimerBs diseaseM4 Neurochemistry

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of Sciences (). 72+9/ 0!+*4 )OI / *4 *!,:pnas4*"*,2!+ *2 4edit

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64 % %aughton; )4 %4Z Lheeler; S4 @4Z %unt; G4 G4Z Lolstenholme; A4 &4 72**294M=he -Subunit o3 Caenorhabditis elegans A>ermectin eceptor esponds to Gl cineand is (ncoded b Chromosome M4 Journal of Neurochemistry -+ 7"9/ 2,"+ 2,"!4

)OI / *4 *+6:J4 +! -+ "#4 ##"46+*"2,"+4 4 P1I) !",60 4edit
http://en.wikipedia.org/wiki/Glutamic_acid#cite_ref-5http://www.jpo.go.jp/seido_e/rekishi_e/kikunae_ikeda.htmhttp://en.wikipedia.org/wiki/Japan_Patent_Officehttp://en.wikipedia.org/wiki/Japan_Patent_Officehttp://en.wikipedia.org/wiki/Glutamic_acid#cite_ref-springerlink_6-0http://en.wikipedia.org/wiki/Glutamic_acid#cite_ref-springerlink_6-0http://en.wikipedia.org/wiki/Glutamic_acid#cite_ref-springerlink_6-1http://en.wikipedia.org/wiki/Digital_object_identifierhttp://dx.doi.org/10.1007%2Fs11738-011-0801-1http://en.wikipedia.org/w/index.php?title=Template:Cite_doi/10.1007.2Fs11738-011-0801-1&action=edit&editintro=Template:Cite_doi/editintro2http://en.wikipedia.org/wiki/Glutamic_acid#cite_ref-pmid10736372_7-0http://en.wikipedia.org/wiki/PubMed_Identifierhttp://www.ncbi.nlm.nih.gov/pubmed/10736372http://www.ncbi.nlm.nih.gov/pubmed/10736372http://en.wikipedia.org/w/index.php?title=Template:Cite_pmid/10736372&action=edit&editintro=Template:Cite_pmid/editintro2http://en.wikipedia.org/wiki/Glutamic_acid#cite_ref-8http://en.wikipedia.org/wiki/Digital_object_identifierhttp://dx.doi.org/10.1007%2FBF02253527http://en.wikipedia.org/wiki/PubMed_Identifierhttp://www.ncbi.nlm.nih.gov/pubmed/7870979http://en.wikipedia.org/w/index.php?title=Template:Cite_doi/10.1007.2FBF02253527&action=edit&editintro=Template:Cite_doi/editintro2http://en.wikipedia.org/wiki/Glutamic_acid#cite_ref-9http://en.wikipedia.org/wiki/Digital_object_identifierhttp://dx.doi.org/10.1073%2Fpnas.0913154107http://en.wikipedia.org/w/index.php?title=Template:Cite_doi/10.1073.2Fpnas.0913154107&action=edit&editintro=Template:Cite_doi/editintro2http://en.wikipedia.org/wiki/Glutamic_acid#cite_ref-10http://en.wikipedia.org/wiki/Digital_object_identifierhttp://dx.doi.org/10.1016%2Fj.brainresrev.2004.04.004http://en.wikipedia.org/wiki/PubMed_Identifierhttp://en.wikipedia.org/wiki/PubMed_Identifierhttp://www.ncbi.nlm.nih.gov/pubmed/15210307http://www.ncbi.nlm.nih.gov/pubmed/15210307http://en.wikipedia.org/w/index.php?title=Template:Cite_doi/10.1016.2Fj.brainresrev.2004.04.004&action=edit&editintro=Template:Cite_doi/editintro2http://en.wikipedia.org/w/index.php?title=Template:Cite_doi/10.1016.2Fj.brainresrev.2004.04.004&action=edit&editintro=Template:Cite_doi/editintro2http://en.wikipedia.org/wiki/Glutamic_acid#cite_ref-11http://en.wikipedia.org/wiki/PubMed_Identifierhttp://en.wikipedia.org/wiki/PubMed_Identifierhttp://www.ncbi.nlm.nih.gov/pubmed/2568579http://www.ncbi.nlm.nih.gov/pubmed/2568579http://en.wikipedia.org/w/index.php?title=Template:Cite_pmid/2568579&action=edit&editintro=Template:Cite_pmid/editintro2http://en.wikipedia.org/wiki/Glutamic_acid#cite_ref-12http://en.wikipedia.org/wiki/Digital_object_identifierhttp://dx.doi.org/10.1016%2Fj.neuint.2004.03.007http://en.wikipedia.org/wiki/PubMed_Identifierhttp://www.ncbi.nlm.nih.gov/pubmed/15234100http://en.wikipedia.org/w/index.php?title=Template:Cite_doi/10.1016.2Fj.neuint.2004.03.007&action=edit&editintro=Template:Cite_doi/editintro2http://en.wikipedia.org/wiki/Glutamic_acid#cite_ref-13http://en.wikipedia.org/wiki/Digital_object_identifierhttp://dx.doi.org/10.1073%2Fpnas.0503274102http://en.wikipedia.org/w/index.php?title=Template:Cite_doi/10.1073.2Fpnas.0503274102&action=edit&editintro=Template:Cite_doi/editintro2http://en.wikipedia.org/wiki/Glutamic_acid#cite_ref-14http://en.wikipedia.org/wiki/Digital_object_identifierhttp://en.wikipedia.org/wiki/Digital_object_identifierhttp://dx.doi.org/10.1523%2Fjneurosci.1519-07.2007http://en.wikipedia.org/wiki/PubMed_Identifierhttp://www.ncbi.nlm.nih.gov/pubmed/17581946http://en.wikipedia.org/w/index.php?title=Template:Cite_doi/10.1523.2Fjneurosci.1519-07.2007&action=edit&editintro=Template:Cite_doi/editintro2http://en.wikipedia.org/wiki/Glutamic_acid#cite_ref-15http://en.wikipedia.org/wiki/Digital_object_identifierhttp://dx.doi.org/10.1046%2Fj.1471-4159.1995.64052354.xhttp://en.wikipedia.org/wiki/PubMed_Identifierhttp://en.wikipedia.org/wiki/PubMed_Identifierhttp://www.ncbi.nlm.nih.gov/pubmed/7536811http://www.ncbi.nlm.nih.gov/pubmed/7536811http://en.wikipedia.org/w/index.php?title=Template:Cite_doi/10.1046.2Fj.1471-4159.1995.64052354.x&action=edit&editintro=Template:Cite_doi/editintro2http://en.wikipedia.org/wiki/Glutamic_acid#cite_ref-5http://www.jpo.go.jp/seido_e/rekishi_e/kikunae_ikeda.htmhttp://en.wikipedia.org/wiki/Japan_Patent_Officehttp://en.wikipedia.org/wiki/Glutamic_acid#cite_ref-springerlink_6-0http://en.wikipedia.org/wiki/Glutamic_acid#cite_ref-springerlink_6-1http://en.wikipedia.org/wiki/Digital_object_identifierhttp://dx.doi.org/10.1007%2Fs11738-011-0801-1http://en.wikipedia.org/w/index.php?title=Template:Cite_doi/10.1007.2Fs11738-011-0801-1&action=edit&editintro=Template:Cite_doi/editintro2http://en.wikipedia.org/wiki/Glutamic_acid#cite_ref-pmid10736372_7-0http://en.wikipedia.org/wiki/PubMed_Identifierhttp://www.ncbi.nlm.nih.gov/pubmed/10736372http://en.wikipedia.org/w/index.php?title=Template:Cite_pmid/10736372&action=edit&editintro=Template:Cite_pmid/editintro2http://en.wikipedia.org/wiki/Glutamic_acid#cite_ref-8http://en.wikipedia.org/wiki/Digital_object_identifierhttp://dx.doi.org/10.1007%2FBF02253527http://en.wikipedia.org/wiki/PubMed_Identifierhttp://www.ncbi.nlm.nih.gov/pubmed/7870979http://en.wikipedia.org/w/index.php?title=Template:Cite_doi/10.1007.2FBF02253527&action=edit&editintro=Template:Cite_doi/editintro2http://en.wikipedia.org/wiki/Glutamic_acid#cite_ref-9http://en.wikipedia.org/wiki/Digital_object_identifierhttp://dx.doi.org/10.1073%2Fpnas.0913154107http://en.wikipedia.org/w/index.php?title=Template:Cite_doi/10.1073.2Fpnas.0913154107&action=edit&editintro=Template:Cite_doi/editintro2http://en.wikipedia.org/wiki/Glutamic_acid#cite_ref-10http://en.wikipedia.org/wiki/Digital_object_identifierhttp://dx.doi.org/10.1016%2Fj.brainresrev.2004.04.004http://en.wikipedia.org/wiki/PubMed_Identifierhttp://www.ncbi.nlm.nih.gov/pubmed/15210307http://en.wikipedia.org/w/index.php?title=Template:Cite_doi/10.1016.2Fj.brainresrev.2004.04.004&action=edit&editintro=Template:Cite_doi/editintro2http://en.wikipedia.org/wiki/Glutamic_acid#cite_ref-11http://en.wikipedia.org/wiki/PubMed_Identifierhttp://www.ncbi.nlm.nih.gov/pubmed/2568579http://en.wikipedia.org/w/index.php?title=Template:Cite_pmid/2568579&action=edit&editintro=Template:Cite_pmid/editintro2http://en.wikipedia.org/wiki/Glutamic_acid#cite_ref-12http://en.wikipedia.org/wiki/Digital_object_identifierhttp://dx.doi.org/10.1016%2Fj.neuint.2004.03.007http://en.wikipedia.org/wiki/PubMed_Identifierhttp://www.ncbi.nlm.nih.gov/pubmed/15234100http://en.wikipedia.org/w/index.php?title=Template:Cite_doi/10.1016.2Fj.neuint.2004.03.007&action=edit&editintro=Template:Cite_doi/editintro2http://en.wikipedia.org/wiki/Glutamic_acid#cite_ref-13http://en.wikipedia.org/wiki/Digital_object_identifierhttp://dx.doi.org/10.1073%2Fpnas.0503274102http://en.wikipedia.org/w/index.php?title=Template:Cite_doi/10.1073.2Fpnas.0503274102&action=edit&editintro=Template:Cite_doi/editintro2http://en.wikipedia.org/wiki/Glutamic_acid#cite_ref-14http://en.wikipedia.org/wiki/Digital_object_identifierhttp://dx.doi.org/10.1523%2Fjneurosci.1519-07.2007http://en.wikipedia.org/wiki/PubMed_Identifierhttp://www.ncbi.nlm.nih.gov/pubmed/17581946http://en.wikipedia.org/w/index.php?title=Template:Cite_doi/10.1523.2Fjneurosci.1519-07.2007&action=edit&editintro=Template:Cite_doi/editintro2http://en.wikipedia.org/wiki/Glutamic_acid#cite_ref-15http://en.wikipedia.org/wiki/Digital_object_identifierhttp://dx.doi.org/10.1046%2Fj.1471-4159.1995.64052354.xhttp://en.wikipedia.org/wiki/PubMed_Identifierhttp://www.ncbi.nlm.nih.gov/pubmed/7536811http://en.wikipedia.org/w/index.php?title=Template:Cite_doi/10.1046.2Fj.1471-4159.1995.64052354.x&action=edit&editintro=Template:Cite_doi/editintro2


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