title: Chemistry of xylopyranosides.
abstract: 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.
authors.affiliation: Centre for Analysis and Synthesis, Centre for Chemistry and Chemical Engineering, Lund University, P.O. Box 124, SE-221 00 Lund, Sweden.
authors.forename: Karin
authors.initials: K
authors.lastname: Thorsheim
authors.affiliation: Centre for Analysis and Synthesis, Centre for Chemistry and Chemical Engineering, Lund University, P.O. Box 124, SE-221 00 Lund, Sweden.
authors.forename: Anna
authors.initials: A
authors.lastname: Siegbahn
authors.affiliation: Centre for Analysis and Synthesis, Centre for Chemistry and Chemical Engineering, Lund University, P.O. Box 124, SE-221 00 Lund, Sweden.
authors.forename: Richard E
authors.initials: RE
authors.lastname: Johnsson
authors.affiliation: Centre for Molecular Protein Science, Centre for Chemistry and Chemical Engineering, Lund University, P.O. Box 124, SE-221 00 Lund, Sweden.
authors.forename: Henrik
authors.initials: H
authors.lastname: Stålbrand
authors.affiliation: Centre for Analysis and Synthesis, Centre for Chemistry and Chemical Engineering, Lund University, P.O. Box 124, SE-221 00 Lund, Sweden.
authors.forename: Sophie
authors.initials: S
authors.lastname: Manner
authors.affiliation: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, SE-106 91 Stockholm, Sweden.
authors.forename: Göran
authors.initials: G
authors.lastname: Widmalm
authors.affiliation: Centre for Analysis and Synthesis, Centre for Chemistry and Chemical Engineering, Lund University, P.O. Box 124, SE-221 00 Lund, Sweden. Electronic address: ulf.ellervik@chem.lu.se.
authors.forename: Ulf
authors.initials: U
authors.lastname: Ellervik
mesh_terms: D000818:Animals; D006027:Glycosides / Q000737:chemistry*; D006801:Humans; D015394:Molecular Structure; D011714:Pyrans / Q000737:chemistry*; D014994:Xylose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D006027:Glycosides; D011714:Pyrans; D014994:Xylose
keywords: Biology; Conformational analysis; Glycoside synthesis; Modifications; Protective groups; Xylopyranoside