Chirality in Industry II: Developments in the Commercial Manufacture and Applications of Optically...
1
Book reviews CHIRALITY IN INDUSTRY II: DEVELOPMENTS IN THE COMMERCIAL MANUFACTURE AND APPLICATIONS OF OPTICALLY ACTIVE COM- POUNDS, edited by A. N. Collins, G. N. Sheldrake and J. Crosby. Wiley, Chichester, 1997. No. of pages: xiv 412. Hardback: price £125.00, ISBN 0-471-96680-0. Paperback: price £37.50. ISBN 0-471-98284-9. I reviewed the first volume of this series for Flavour and Fragrance Journal, 8, 123 (1993) when many of the com- pounds discussed were related to those used as flavours or fragrances. This second volume has a much larger emphasis on chiral drugs. Indeed, in his Introduction (10 pp.) J. Crosby says that the needs of the pharmaceutical industry are the major driving force for development of the manufacture of optically active compounds. He goes on to review the advances made since the first volume. The second chapter discusses ‘Chiral Drugs: Regulatory Aspects’ (8 pp.) while the third (21 pp.) reviews ‘Production Methods for Chiral Non-steroidal Anti-inflammatory Profen Drugs’. The fourth chapter (37 pp.) deals with the ‘Synthesis of Enantiomerically Pure Nucleosides’ (related to anti-viral drugs). The second section on ‘Physical Methods and Classical Resolution’ is of more general interest. The four chapters discuss ‘Rational Design in Resolutions’ (18 pp.), ‘Resol- ution versus Stereoselective Synthesis in Drug Development: Some Case Histories’ (20 pp.), ‘Crystal Science Techniques in the Manufacture of Chiral Compounds’ (38 pp.) and ‘Membrane Separations in the Production of Optically Pure Compounds’ (24 pp.). The third section on ‘Biological Methods and Chiral Pool Syntheses’ again concentrates on drug intermediates in four of the six chapters. The others deal with the ‘Synthesis and Applications of Chiral Liquid Crystals’ and ‘Bio-transformation in the Production of L-Carnitine’. In the last section, ‘Asymmetric Syntheses by Chemical Methods’, there is one chapter likely to be of more direct interest to readers of this Journal. Chapter 16 (17 pp.), by C. Fehr of Firmenich, discusses ‘Enantioselective Protonation in Fragrance Synthesis’, in particular, the synthesis of (S)-a- damascone and related compounds and a new tetralin musk perfume component. Other chapters discuss the ‘Asymmetric Hydrocyanation of Vinylarenes’ (as a route to profen drugs, 25 pp.), ‘Thiamphenicol: A Manufacturing Process involving a Double Inversion of Stereochemistry’ (10 pp.), ‘Sharpless Asymmetric Epoxidation: Scale-up and Industrial Produc- tion’ (18 pp.), ‘Asymmetric Synthesis of Sulphoxides: Two Case Studies’ (9 pp.) and ‘Asymmetric Reduction of Pro- chiral Ketones’. These chapter titles indicate the wide range of the book which, with the earlier volume, will be required reading for anyone required to produce any amount of a pure enan- tiomer. The paperback editions make the books more aord- able for individual readers. ROGER STEVENS Threlkeld, UK FLAVOUR AND FRAGRANCE JOURNAL Flavour Fragr. J., 13, 424–425 (1998) ANALYTICAL METHODS FOR FOOD AUTHENTICA- TION, edited by P. R. Ashurst and M. J. Dennis, Blackie Academic & Professional, London, 1998. No. of pages x 350, price £79.00. ISBN 0 7514 0426 8 Analytical Methods for Food Authentication comprises 12 chapters written by 16 authors on the principal analytical techniques applicable to the authentication of foods. It follows on from the 1996 book entitled Food Authentication from the same editors, which dealt with authentication by food commodity. Once again, the book is set clearly in 10/12 pt Times and is printed on a good quality white paper. The first chapter is an introduction to methods for food authentication by the editors. They start by asking what food analysts are trying to achieve when they carry out authen- ticity tests. They suggest that food producers, enforcement authorities and national governments have subtly dierent needs. Reputable producers must meet the needs of legisla- tion where their product is sold and wish to ensure that any commodities purchased meet specification. Method validity is crucial to enforcement authorities so that it is defensible in a court of law. Whilst enforcement is normally conducted at a local level, national governments need to co-ordinate and direct these activities and ensure that appropriate research and resources are in place to meet the needs of industry and enforcement authorities, in order to protect the public. The chapter on stable isotope analysis by mass spectro- metry (by D. A. Krueger) deals with the stable isotopes of carbon, oxygen and hydrogen. High precision stable isotope ratio analysis (SIRA) enables the generation of characteristic signatures in materials from dierent regions. It is becoming widely used for the authentication of foodstus and the detection of economic adulteration, including such problems as the origin of carbonation in sparkling wine, sugars in maples syrup and vanillin in vanilla extract. The next chapter, on nuclear magnetic resonance spectroscopy (by I. J. Colqu- houn and M. Lees), deals with high-resolution NMR and site-specific natural isotope fractionation (SNIF) by NMR. The latter technique, which was originally used to detect enrichment of wines (by adding sugar to grape must before fermentation to increase alcohol yield), has now found many applications with other alcohols, fruit juices and flavours. Other chapters follow on infrared spectroscopy by (C. N. G. Scotter and R. Wilson), covering both mid- and near-infrared and its applications, and oligosaccharide analysis (by N. Low), a chapter containing many useful chromato- grams. Enzymatic methods of food analysis (by G. Henniger) describes this analysis as an independent and separate branch # 1998 John Wiley & Sons, Ltd. CCC 0882–5734/98/060424–02$17.50
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Transcript of Chirality in Industry II: Developments in the Commercial Manufacture and Applications of Optically...
Book reviews
CHIRALITY IN INDUSTRY II: DEVELOPMENTS INTHE COMMERCIAL MANUFACTURE AND
APPLICATIONS OF OPTICALLY ACTIVE COM-POUNDS, edited by A. N. Collins, G. N. Sheldrake andJ. Crosby. Wiley, Chichester, 1997. No. of pages: xiv � 412.
Hardback: price £125.00, ISBN 0-471-96680-0. Paperback:price £37.50. ISBN 0-471-98284-9.
I reviewed the ®rst volume of this series for Flavour and
Fragrance Journal, 8, 123 (1993) when many of the com-pounds discussed were related to those used as ¯avours orfragrances. This second volume has a much larger emphasis
on chiral drugs. Indeed, in his Introduction (10 pp.) J. Crosbysays that the needs of the pharmaceutical industry are themajor driving force for development of the manufacture of
optically active compounds. He goes on to review theadvances made since the ®rst volume. The second chapterdiscusses `Chiral Drugs: Regulatory Aspects' (8 pp.) while
the third (21 pp.) reviews `Production Methods for ChiralNon-steroidal Anti-in¯ammatory Profen Drugs'. The fourthchapter (37 pp.) deals with the `Synthesis of EnantiomericallyPure Nucleosides' (related to anti-viral drugs).
The second section on `Physical Methods and ClassicalResolution' is of more general interest. The four chaptersdiscuss `Rational Design in Resolutions' (18 pp.), `Resol-
ution versus Stereoselective Synthesis in Drug Development:Some Case Histories' (20 pp.), `Crystal Science Techniques inthe Manufacture of Chiral Compounds' (38 pp.) and
`Membrane Separations in the Production of Optically PureCompounds' (24 pp.). The third section on `Biological
Methods and Chiral Pool Syntheses' again concentrates ondrug intermediates in four of the six chapters. The others dealwith the `Synthesis and Applications of Chiral Liquid
Crystals' and `Bio-transformation in the Production ofL-Carnitine'.In the last section, `Asymmetric Syntheses by Chemical
Methods', there is one chapter likely to be of more direct
interest to readers of this Journal. Chapter 16 (17 pp.), by C.Fehr of Firmenich, discusses `Enantioselective Protonation inFragrance Synthesis', in particular, the synthesis of (S)-a-damascone and related compounds and a new tetralin muskperfume component. Other chapters discuss the `AsymmetricHydrocyanation of Vinylarenes' (as a route to profen drugs,
25 pp.), `Thiamphenicol: A Manufacturing Process involvinga Double Inversion of Stereochemistry' (10 pp.), `SharplessAsymmetric Epoxidation: Scale-up and Industrial Produc-
tion' (18 pp.), `Asymmetric Synthesis of Sulphoxides: TwoCase Studies' (9 pp.) and `Asymmetric Reduction of Pro-chiral Ketones'.These chapter titles indicate the wide range of the book
which, with the earlier volume, will be required reading foranyone required to produce any amount of a pure enan-tiomer. The paperback editions make the books more a�ord-
able for individual readers.ROGER STEVENS
Threlkeld, UK
FLAVOUR AND FRAGRANCE JOURNAL
Flavour Fragr. J., 13, 424±425 (1998)
ANALYTICAL METHODS FOR FOOD AUTHENTICA-
TION, edited by P. R. Ashurst and M. J. Dennis, BlackieAcademic & Professional, London, 1998. No. of pagesx � 350, price £79.00. ISBN 07514 0426 8
Analytical Methods for Food Authentication comprises12 chapters written by 16 authors on the principal analyticaltechniques applicable to the authentication of foods. It
follows on from the 1996 book entitled Food Authenticationfrom the same editors, which dealt with authentication byfood commodity. Once again, the book is set clearly in
10/12 pt Times and is printed on a good quality white paper.The ®rst chapter is an introduction to methods for food
authentication by the editors. They start by asking what food
analysts are trying to achieve when they carry out authen-ticity tests. They suggest that food producers, enforcementauthorities and national governments have subtly di�erentneeds. Reputable producers must meet the needs of legisla-
tion where their product is sold and wish to ensure that anycommodities purchased meet speci®cation. Method validity iscrucial to enforcement authorities so that it is defensible in a
court of law. Whilst enforcement is normally conducted at alocal level, national governments need to co-ordinate anddirect these activities and ensure that appropriate research
and resources are in place to meet the needs of industry and
enforcement authorities, in order to protect the public.The chapter on stable isotope analysis by mass spectro-
metry (by D. A. Krueger) deals with the stable isotopes of
carbon, oxygen and hydrogen. High precision stable isotoperatio analysis (SIRA) enables the generation of characteristicsignatures in materials from di�erent regions. It is becomingwidely used for the authentication of foodstu�s and the
detection of economic adulteration, including such problemsas the origin of carbonation in sparkling wine, sugars inmaples syrup and vanillin in vanilla extract. The next chapter,
on nuclear magnetic resonance spectroscopy (by I. J. Colqu-houn and M. Lees), deals with high-resolution NMR andsite-speci®c natural isotope fractionation (SNIF) by NMR.
The latter technique, which was originally used to detectenrichment of wines (by adding sugar to grape must beforefermentation to increase alcohol yield), has now found manyapplications with other alcohols, fruit juices and ¯avours.
Other chapters follow on infrared spectroscopy by (C. N. G.Scotter and R. Wilson), covering both mid- and near-infraredand its applications, and oligosaccharide analysis (by N.
Low), a chapter containing many useful chromato-grams. Enzymatic methods of food analysis (by G. Henniger)describes this analysis as an independent and separate branch
# 1998 John Wiley & Sons, Ltd. CCC 0882±5734/98/060424±02$17.50
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