Thioglycosidic linkage

Scheme 1.2 Solid-phase oligosaccharide synthesis employing thioglycosidic linkages to different solid supports.

Scheme 11. The thioglycoside linkage in 50 was activated to yield methyl glycoside 51 (DTBP, 2,6-di-tert-butyl-pyridine).

Scheme 12. The activation of a thioglycoside linkage such as 52 enables the usage of galactose as a five-dimension diversity scaffold.

Conformational equilibria of thio-oligosaccharides revealed that the most important thiodisac-charide (4-thio-a-maltoside) has a conformation similar to that of the parent maltosyl residue and that the thioglycoside linkage presents a high degree of flexibility. Interestingly, the C-S... 

H. Hashimoto, K. Shimada, and S. Horito, Synthesis of a-L-fucopyranosyl disaccharides with thioglycosidic linkages and characterization of a-L-fucosidases from bovine kidney and epididymis by their inhibitory activities, Tetrahedron Asymmetry, 5 (1994) 2351-2366. 

Glycocin F, secreted by Lactobacillus plantarum KW30, was characterized and led to the identification of an unexpected N-acetylglucosamine bound to a Cysteine by a thioglycosidic linkage. Further studies by structural nuclear magnetic resonance confirmed the presence of two N-acetylglucosamine moieties, one attached to a Serine o g gen atom, the second to a Cysteine sulfur atom. ... 

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