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Several O-and N-linked inositols and/or aminoinositols have been prepared by iterative opening of epoxides and aziridines derived from homochiral cyclohexadiene cis-diols. The three inositols and their intermediate conduritols (conduramines) were tested against several glycosidases (alpha- and beta-glucosidase, alpha- and beta-galactosidase, alpha- and beta-mannosidase) in an assay that measured the rate of hydrolysis of p-nitrophenolglycosides rather than the concentration of p-nitrophenolate. Somewhat surprisingly, the best inhibition was seen against beta-galactosidase with several of the compounds. The inositols linked through oxygen or nitrogen were subjected to calcium binding studies performed in NMR experiments. Detailed analysis of the title compounds by NMR spectroscopy has been performed, and full assignments were made. One of the attendant benefits of the preparation of these compounds has been expressed in the design and synthesis of new salen catalysts whose effectiveness has been compared with Jacobsen's catalyst in the epoxidation of styrene.

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Recent applications of glycosyl fluorides as donors in controlled di- and oligosaccharide synthesis employing chemical and enzymatic methods are presented. Within the chemical approaches significant contributions have been made by the development of fluorophilic activators displaying high stereoselectivity as well as further improvements in "reactivity fine tuning" by variation of protecting groups. In the field of enzymatic oligosaccharide synthesis progress has been made in regioselective glycosyl transfer to secondary hydroxyl groups. Additionally, promising new approaches employing fluorides derived from monosaccharides with specifically mutated glycosidases or disaccharide derived fluorides with cellulases, have been developed. From the numerous contributions regarding the synthesis of deoxy-fluoro aldoses, emphasis is placed upon side-reactions on attempted nucleophilic substitutions. Within this field modification of pentoses at C-2 using the sulfonate/fluoride route or applying diethylaminosulfur trifluoride are discussed. The increasing use of asymmetric synthesis in this field, including a new entry starting from a chiral cis-diol, is noteworthy. Scope and limitations in the synthesis of 2-deoxy-2-fluoro aldoses by electrophilic addition across the double bond of glycals by making use of the new class of N-F-fluorinating agents are presented. The important role of fluorinated carbohydrates as probes in mechanistic enzyme studies as well as their application in biomedical research is illustrated by several examples.

Syntheses of various (2-deoxy-2-fluoro-glycosyl-)amino-acids are described. This new class of acid stable glycoconjugates was accessible by electrophilic fluorination of glycals, followed by coupling with suitable protected serine and aspartic acid derivates.