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exo-Glycal Chemistry: General Aspects and Synthetic Applications for Biochemical Use

[ Vol. 5 , Issue. 14 ]

Author(s):

Chun-Hung Lin, Hui-Chang Lin and Wen-Bin Yang   Pages 1431 - 1457 ( 27 )

Abstract:


It is well known that carbohydrates play an indispensable role in a variety of essential biological activities, such as cell-cell adhesion, bacteria and virus infections, and tumor metastasis. Among an increasing number of sugars and sugar mimetics that have been designed and synthesized for the purpose of drug discovery, C-glycosides are considered to be one of the best choices on account of their stability and resemblance as they differ from normal glycosides only in glycosidic linkages. exo-Glycals are unsaturated sugars that have a double bond attached to the anomeric center outside the sugar ring. These carbohydrate molecules are useful for the synthesis of C-glycosides and compounds containing quaternary carbons, provided that the olefin can be properly reduced or functionalized. This review places special emphasis on two aspects of exo-glycals including general methods of preparation and synthetic applications for making biologically important molecules. The first half discusses the methods of addition/elimination and Ramburg-B├Ącklund rearrangement that offer many beneficial features including a wide range of double bond substitutions, limited reaction steps, easy operation and good overall yields. The rest of the article demonstrates a number of synthetic studies using exoglycals as the starting materials. The target molecules can be categorized into three groups, namely C-glycosides, enzyme inhibitors and bioactive natural products.

Keywords:

exo-glycal, C-glycoside, addition, elimination, glycosylation, quaternary carbon, inhibitor, rearrangement

Affiliation:

Institute of BiologicalChemistry, Academia Sinica, No.128 Academia Road Section 2, Nan-Kang,Taipei, 11529, Taiwan.



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