Chemistry of xylopyranosides

• Published in: Carbohydrate research Vol. 418; pp. 65 - 88
• Main Authors: Thorsheim, Karin, Siegbahn, Anna, Johnsson, Richard E., Stålbrand, Henrik, Manner, Sophie, Widmalm, Göran, Ellervik, Ulf
• Format: Journal Article
• Language: English
• Published: Netherlands Elsevier Ltd 11.12.2015
• Subjects: Animals; Biochemistry and Molecular Biology; Biokemi och molekylärbiologi; Biologi; Biological Sciences; Biology; Conformational analysis; Glycoside synthesis; Glycosides - chemistry; Humans; Modifications; Molecular Structure; Natural Sciences; Naturvetenskap; Protective groups; Pyrans - chemistry; Xylopyranoside; Xylose - analogs & derivatives; Xylose - chemical synthesis; Xylose - chemistry; Modifications; Glycoside synthesis; Biology; Protective groups; Xylopyranoside; Conformational analysis
• ISSN: 0008-6215; 1873-426X; 1873-426X
• DOI: 10.1016/j.carres.2015.10.004

Xylose is one of the few monosaccharidic building blocks that are used by mammalian cells. In comparison with other monosaccharides, xylose is rather unusual and, so far, only found in two different mammalian structures, i.e. in the Notch receptor and as the linker between protein and glycosaminoglycan (GAG) chains in proteoglycans. Interestingly, simple soluble xylopyranosides can not only initiate the biosynthesis of soluble GAG chains but also function as inhibitors of important enzymes in the biosynthesis of proteoglycans. Furthermore, xylose is a major constituent of hemicellulosic xylans and thus one of the most abundant carbohydrates on Earth. Altogether, this has spurred a strong interest in xylose chemistry. The scope of this review is to describe synthesis of xylopyranosyl donors, as well as protective group chemistry, modifications, and conformational analysis of xylose.