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Glycosylimidates, 54. Synthesis of the GlcNAcβ(1→4)MurNAcβ(1→4)GlcNAcβ(1→4)MurNAc tetrasaccharide of bacterial peptidoglycan
Author(s) -
Termin Andreas,
Schmidt Richard R.
Publication year - 1992
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199219920191
Subject(s) - chemistry , disaccharide , tetrasaccharide , glycosyl donor , glycosyl , stereochemistry , muramic acid , acetylation , peptidoglycan , aminosugar , glucosamine , organic chemistry , polysaccharide , biochemistry , cell wall , gene
From 2‐azido‐2‐deoxy‐ D ‐glucose have been prepared at 1‐O and/or 4‐O selectively protected glucosamine and muramic acid derivatives, which were transformed into glycosyl donors 6 and 14a, b and into glycosyl acceptors 7 and 15 . The reaction of these donors and acceptors yielded disaccharides 8 and 11–13 . Selective 1a‐ O ‐deprotection of disaccharide 12 and subsequent treatment with trichloroacetonitrile afforded disaccharide donor 17 ; selective removal of the 4b‐ O ‐protective groups in disaccharides 8 and 11 furnished disaccharide acceptor 9 . These building blocks were employed in the synthesis of β‐connected tetrasaccharide 18 which gave upon azido group reduction, acetylation of the amino groups, and complete O ‐deprotection the desired target molecule 1 characterized as its fully O ‐acetylated product 2 .