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Multi‐Gram Synthesis of a Hyaluronic Acid Subunit and Synthesis of Fully Protected Oligomers
Author(s) -
Virlouvet Mickaël,
Gartner Michael,
Koroniak Katarzyna,
Sleeman Jonathan P.,
Bräse Stefan
Publication year - 2010
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201000008
Subject(s) - chemistry , hyaluronic acid , glycosylation , hexa , disaccharide , gram , stereochemistry , protein subunit , combinatorial chemistry , biochemistry , bacteria , genetics , gene , biology
Fully protected tetra‐, hexa‐ and octasaccharides of hyaluronic acid were synthesized on a scale of several 100 mg up to gram quantities using allyl (methyl 2‐ O ‐benzoyl‐3‐ O ‐benzyl‐4‐ O ‐levulinoyl‐ β ‐ D ‐glucopyranosyluronate)‐(1→3)‐4‐ O ‐acetyl‐6‐ O ‐benzyl‐2‐deoxy‐2‐trichloroacetamido‐ β ‐ D ‐glucopyranoside as a key building block. This disaccharide was subjected to deprotection, then glycosylation via the trichloroacetimidate method was employed to achieve the formation of the oligosaccharides.