Carbohydrate Chemistry by D. R. Bundle, G. Descotes, J. Gigg, R. Gigg, W. Klaffke, B.

By D. R. Bundle, G. Descotes, J. Gigg, R. Gigg, W. Klaffke, B. Meyer, J. Staněk, T. Suami, J. Thiem (auth.)

Contents: D.R. package deal, Ottawa, Ont., Canada: Synthesis of Oligosaccharides relating to Bacterial O-AntigensG. Descotes, Villeurbanne, France: Synthetic Saccharide PhotochemistryJ. Gigg, R. Gigg, London, united kingdom: Synthesis of GlycolipidsB. Meyer, Athens, GA, united states: Conformational points of OligosaccharidesJ. Stanek, Jr., Prague, CSFR: Preparation ofSelectively Alkylated Saccharides as artificial IntermediatesT. Suami, Tokyo, Japan: Chemistry of Pseudo-SugarsJ. Thiem, W. Klaffke, Hamburg, FRG: Syntheses of Deoxy Oligosaccharides

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Kochetkov NK, Shibaev VN, Druzhinina TN, Gogilashvili LM, Danilov LL, Torgov VI, Mattsev SD, Utkina NS (1982) Dokl Akad Nauk SSSR 262: 1393; (1982) Chem Abstr 97: 106402a 59. Ekborg G, L6nngren J, Svensson S (1975) Acta Chem Scand Ser B29:1031 60. Kochetkov NK, Klimov EM, Torgov VI (1976) Izv Akad Nauk SSSR Ser Khim 165; (1976) Chem Abstr 85:332965 61. Kochetkov NK, Dmitriev BA, Chernyak AYa, Pokrovskii VI, Tendetnik YY (1979) Bioorg Khim 5: 217; (1979) Chern Abstr 90: 187248k 62. Kochetkov MK, Dmitriev BA, Chernyak AYa, Levinsky AB (1982) Carbohydr Res 110, C16 63.

Nevertheless, a facile synthesis of dihydroshowdomycin [54] uses the same type of photoaddition of amides on unsaturated sugars following Scheme 26. 20xycarbinyl Radicals A general study of the photochemical addition of 2-propanol and 1,3-dioxolane to unsaturated sugars [48, 55, 56] shows the following order of reactivity (see Scheme 27) and yields mixtures of stereoisomers. ,o 0 / Ac0-1 o(-> Ac \OAc decreasing reactivity Scheme 27 Recently, more efficient photochemical additions are described on the enol bonds at C-5, C-6 of unsaturated sugars.

First steps have already been reported in this area as applied to O-polysaccharides [58]. Since the enzyme complex responsible for the construction and polymerization of repeating units is membrane bound, it seems certain that progress in this area will be slow. It is encouraging to note, however, that the genes responsible for the synthesis and assembly of one bacterial O-polysaccharide, that of Vibrio cholerae have been cloned and expressed in E. coli [135]. Potential access to the genes coding for enzymes that perform O-polysaccharide synthesis is thus within sight.

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