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Transcript of Invertebrati marini Prof. Giorgio Sartor Copyright © 2001-2008 by Giorgio Sartor. All rights...
![Page 1: Invertebrati marini Prof. Giorgio Sartor Copyright © 2001-2008 by Giorgio Sartor. All rights reserved. G03 - Versione 1.3 – dec 2008 I glucidi.](https://reader035.fdocuments.in/reader035/viewer/2022070312/5542eb4e497959361e8bc1c0/html5/thumbnails/1.jpg)
Invertebrati marini
Prof. Giorgio Sartor
Copyright © 2001-2008 by Giorgio Sartor.
All rights reserved.
G03 - Versione 1.3 – dec 2008
I glucidi
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V.1.3 © gsartor 2001-2008 Invertebrati marini - I glucidi - 2 -
Glicosidasi
• Così come per le proteine anche i polimeri glucidici vengono scissi in monomeri attraverso l’idrolisi di un legame glicosidico.
• Diversi sono i monomeri coinvolti nella formazione dei polisaccaridi di origine algale marina:– fucoso, – glucoso, – galattoso, – mannoso,– xyloso, – ramnoso
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Monomeri
OH
OHOH
OHO
OH
Galattoso
OH
OHOH
OHO
OH
Glucoso
OH
OHOH
OHO
OH
Mannoso
OH
OH
OH
OOH
Xiloso
OH
OH
OH
OCH3
OH
Ramnoso
OH
OH
OH
O
CH3
OH
Fucoso
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Omopolisaccaridi
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Eteropolisaccaridi
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• Glucosaminoglicani
• Alginati
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Fucoidan hydrolase and glycosidase activities in marine invertebrates
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Fucoidan hydrolase and glycosidase activity in marine invertebrates
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Glicosidasi
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Glicosidasi (EC 3.2.1.-)• 1. Ossidoreduttasi• 2. Transferasi• 3. Idrolasi
– 3.1 Agisce su legami esterei– 3.2 Glicosilasi
• 3.2.1 Glicosidasi, idrolizzano composti O- e S-glicosilici• 3.2.2 Idrolizzano composti N-glicosilici• 3.2.3 sottoclasse cancellata (Idrolizzano composti S-glicosilici)
– 3.3 Agisce su legami etere– 3.4 Agisce su legami peptidici (peptidasi)– 3.5 Agisce su legami C-N diversi da legame peptidico– 3.6 Agisce su legami anidride– 3.7 Agisce su legami C-C– 3.8 Agisce su legami alide– 3.9 Agisce su legami P-N– 3.10 Agisce su legami S-N– 3.11 Agisce su legami C-P– 3.12 Agisce su legami S-S– 3.13 Agisce su legami C-S
• 4. Liasi• 5. Isomerasi• 6. Ligasi
EC 3.2.1.1 – EC 3.2.1.165
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Meccanismi catalitici
• Le glicosidasi agiscono con idrolisi del legame glicosidico con due prodotti principali:– Monomeri con medesima configurazione del
carbonio anomerico• Intermedio ione ossonio (lisozima)• Intermedio covalente (-1,4-glicosidasi)
– Monomeri con inversione della configurazione del carbonio anomerico
• Stato di transizione ione ossicarbene
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V.1.3 © gsartor 2001-2008 Invertebrati marini - I glucidi - 12 -
Meccanismi catalitici
• Le glicosidasi agiscono con idrolisi del legame glicosidico con due prodotti principali:– Monomeri con medesima configurazione del
carbonio anomerico• Intermedio ione ossonio (lisozima)• Intermedio covalente (-1,4-glicosidasi)
– Monomeri con inversione della configurazione del carbonio anomerico
• Stato di transizione ione ossicarbene
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Intermedio ione ossonio
OR'OOH OR"
NHAc
OH
*
ONH2
*
OO H
*
OO
*
OO
*
OO
O+
R'OOH
NHAc
OH
*
ONH2
H
O R"
H
OR"
H
O H
*
OO H
*
OO
R'O
OHNHAc
OR"
OH
OR'O
OHNHAc
OH
OH
*
OO
*
OO
O+
R'OOH
NHAc
OH
*
ONH2
H
O H
*
ONH2
OR'OOH OH
NHAc
OH
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Lisozima
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Lisozima (EC 3.2.1.17)
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Lisozima (EC 3.2.1.17)
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Lisozima (EC 3.2.1.17)
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Intermedio covalente
OR'OOH
OR"
OH
OH
*
OO H
*
OO
*
OO
H
*
OO
OR'OOH
O
OH
OH
R"
H
OR"
*
OO
H
*
OO
OR'OOH
O
OH
OH
H
H
O H
OR'OOH
OH
OH
OH
*
OO H
*
OO
*
OO
*
OO
OR'OOH
OH
OH
R'O
OHOH
OR"
OH
OR'O
OHOH
OH
OH
+
+
alto pKa basso pKa
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Stato di transizione ione ossicarbene
*
OO
*
OOH
O
OH
OH
OR"
OH
O OOH
OH
OH
OH
O
OH
OH
OR"
OH
O OOH
OH
OH
OH
H
O H
H
*
OO
OH
OOH
OH
OH
OH
O
OH
OH
OR"
OH
O
H
*
OOO
OH
OH
OR"
OH
OHOOH
OH
OH
OH
OH
H
O H
*
OO
O
OH
OH
OR"
OH
O OOH
OH
OH
OHOO
H
*
+
+
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Ritenzione della configurazione
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Ritenzione della configurazione
• Senza formazione di un intermedio covalente
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Inversione della configurazione
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GLicogenasi (EC 3.2.1.1)
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GLicogenasi (EC 3.2.1.1)
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Laminarina
O
OHOH
OH
OH
O OH
OH
O
OH
O
OH
OH
O
OH
OH
n
-13
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Laminaranasi - EC 3.2.1.6
2CL2
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V.1.3 © gsartor 2001-2008 Invertebrati marini - I glucidi - 27 -
Fucoidan
O
O
*
O
CH3
SO
O
OO
O
OH
*
OH
CH3
OS
O
OO
n
O
OH
O
CH3
S
*
OO
O
O*n
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-L-fucosidasi - EC 3.2.1.44
2CL2
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Agarasi (EC 3.2.1.81)
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PROTEINE POLISACCARIDI LIPIDI
Aminoacidi Esosi; Pentosi Ac. Grassi; Glicerolo
ATP
ADP + PiATP
Piruvato
ATP
O2
ADP + Pi ADP + Pi
ATP
ADP + Pi
ATP
ADP + Pi
AcetilCoA
ATP
ADP + Pi
-chetoacidiATP
ADP + Pi
ATP
ADP + Pi
CO2H2ONH3
IIFASE OSSIDATIVA
IFASE IDROLITICA
III
Metabolismodei glucidi
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Crediti e autorizzazioni all’utilizzo• Questo materiale è stato assemblato da informazioni raccolte dai seguenti testi di Biochimica:
– CHAMPE Pamela , HARVEY Richard , FERRIER Denise R. LE BASI DELLA BIOCHIMICA [ISBN 978-8808-17030-9] – Zanichelli
– NELSON David L. , COX Michael M. I PRINCIPI DI BIOCHIMICA DI LEHNINGER - Zanichelli – GARRETT Reginald H., GRISHAM Charles M. BIOCHIMICA con aspetti molecolari della Biologia
cellulare - Zanichelli– VOET Donald , VOET Judith G , PRATT Charlotte W FONDAMENTI DI BIOCHIMICA [ISBN 978-8808-
06879-8] - Zanichelli
• E dalla consultazione di svariate risorse in rete, tra le quali:– Kegg: Kyoto Encyclopedia of Genes and Genomes http://www.genome.ad.jp/kegg/– Brenda: http://www.brenda.uni-koeln.de/– Protein Data Bank: http://www.rcsb.org/pdb/ – Rensselaer Polytechnic Institute:
http://www.rpi.edu/dept/bcbp/molbiochem/MBWeb/mb1/MB1index.html
Questo ed altro materiale può essere reperito a partire da:http://www.ambra.unibo.it/giorgio.sartor/ oppure da http://www. gsartor.org/
Il materiale di questa presentazione è di libero uso per didattica e ricerca e può essere usato senza limitazione, purché venga riconosciuto l’autore usando questa frase:
Materiale ottenuto dal Prof. Giorgio SartorUniversità di Bologna a Ravenna
Giorgio Sartor - [email protected]