Cellobiose analogues

Reaction of 1,6-anhydro-il, 6 - -benzylidene-3-maltose with 1,3-dlchloro-l,l,3,3-tetraisopropyldislloxane (1.e. TIPS-CI2) in pyridine yielded the 2, 3 -0 -TIPS ether, while the cellobiose analogue yielded the 2,3-0 -TIPS ether (1.e. substituted on the anhydro-sugar moiety). Discrimination between the 2,3- and 2, 3 -hydroxy groups of maltose and cellobiose can be effected in this... 

R. G. Edwards, L. Hough, and A. C. Richardson, Transformations of cellobiose derivatives into analogues of lactose, Carbohydr. Res., 55 (1977) 129-148. 

B. W. Sigurdskjold, B. Duus, and K. Bock, Hydrolysis of substrate analogues catalysed by P-D-glucosidase from Aspergillus niger. Part II Deoxy and deoxyhalo derivatives of cellobiose, Acta Chem. Scand., 45 (1991) 1032-1041. 

In contrast to this relatively high specificity of cellobiose oxidoreductases for P-I,4-linked di- or oligosaccharides they are highly non-specific with respect to the electron acceptor and can reduce a wide range of quinones, quinone-analogue dyes such as dichloroindophenol, organic radical species, and variously complexed metal ions (29, 33). Some of these electron acceptors of S. rolfsii CDH together with their kinetic constants are listed in Table III. 

The keto-disaccharide nucleoside analogue (34) has been synthesized from B-cellobiosyl or 3-D-glucopyranosyl derivatives of theophylline. 6 -Deoxygenation of the glucosyl derivative followed by glycosylation to the disaccharide with subsequent standard conversion of the terminal unit to the unsaturated keto sugar was found to be preferable because of the unreactivity of the 6 -hydroxy group in the cellobiose precursor. ... 

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