Synthesis of a natural oligosaccharide antibiotic active against Helicobacter pylori

Shino Manabe, Kazuyuki Ishii, Yukishige Ito

Research output: Contribution to journalArticlepeer-review

44 Citations (Scopus)

Abstract

(Chemical Equation Presented) An oligosaccharide active against Helicobacter pylori was synthesized in a highly efficient manner for the first time. The anti-H. pylori oligosaccharide structure is a core-2 branched-type oligosaccharide with a characteristic α-N-acetylglucosamine at the nonreducing end. The oligosaccharide was synthesized from the nonreducing end to the reducing end, with an N-benzyl-2,3-oxazolidinone-carrying glycosyl donor used to introduce an α-N-acetylglucosamine at the nonreducing end. Complete chemoselective activation of a bromo sugar in the presence of a thioglycoside acceptor was achieved, and the use of 2,6-dimethylphenyl thioglycoside prevented the aglycon transfer observed when the corresponding phenyl thioglycoside is used as an acceptor.

Original languageEnglish
Pages (from-to)6107-6115
Number of pages9
JournalJournal of Organic Chemistry
Volume72
Issue number16
DOIs
Publication statusPublished - 2007 Aug 1
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Synthesis of a natural oligosaccharide antibiotic active against Helicobacter pylori'. Together they form a unique fingerprint.

Cite this