Stereo- and Regioselective Synthesis of O-Mannosyl Glycan Containing Matriglycan and a Part of Tandem Ribitol Phosphate

We herein successfully synthesized two pivotal structures of O-mannosyl glycan: (1) the matriglycan-repeating tetrasaccharide Xyl alpha 1-3GIcA beta 1-3Xyl alpha 1-3GlcA beta and (2) the link between matriglycan and a part of tandem ribitol phosphate, Xyl alpha 1-3GlcA beta 1-4Xyl beta 1-4Rbo, in a...

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Published inJournal of organic chemistry Vol. 85; no. 20; pp. 12935 - 12946
Main Authors Tamura, Takahiro, Omura, Yuka, Tamura, Jun-ichi
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 16.10.2020
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
MUSCULAR-DYSTROPHY
ACID
GLYCOSYLATION
DYSTROGLYCAN
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Summary:We herein successfully synthesized two pivotal structures of O-mannosyl glycan: (1) the matriglycan-repeating tetrasaccharide Xyl alpha 1-3GIcA beta 1-3Xyl alpha 1-3GlcA beta and (2) the link between matriglycan and a part of tandem ribitol phosphate, Xyl alpha 1-3GlcA beta 1-4Xyl beta 1-4Rbo, in a regio- and stereocontrolled manner. The disaccharide unit with the alpha-linkage of xylose was obtained by adopting the conformational fixation of the xylopyranoside ring and a specific solvation system of diastereoselective solubility.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c01569