First Total Synthesis of the Re-Type Lipopolysaccharide

Three sequential efficient glycosylation reactions starting from D‐glucosamine were used in the first total synthesis of Escherichia coli Re lipopolysaccharide, which is one of the most simple lipopolysaccharides found on the surface of living bacteria.

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Bibliographic Details
Published inAngewandte Chemie International Edition Vol. 40; no. 8; pp. 1475 - 1480
Main Authors Yoshizaki, Hiroaki, Fukuda, Naohiro, Sato, Kenjiro, Oikawa, Masato, Fukase, Koichi, Suda, Yasuo, Kusumoto, Shoichi
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag GmbH 17.04.2001
WILEY‐VCH Verlag GmbH
Wiley
Subjects
Chemistry
Chemistry, Multidisciplinary
glycolipids
glycosylations
lipopolysaccharides
natural products
Physical Sciences
Science & Technology
total synthesis
LIPID-A ANALOGS
3-DEOXY-D-MANNO-2-OCTULOSONIC ACID KDO
BIOSYNTHETIC PRECURSOR
DIVERGENT SYNTHESIS
BIOLOGICAL-ACTIVITIES
SHORTER ACYL CHAINS
ANOMERIC O-ALKYLATION
ALPHA-GLYCOSIDES
GLYCOSYL FLUORIDES
STEREOCONTROLLED GLYCOSIDATIONS
natural products
glycolipids
lipopolysaccharides
total synthesis
glycosylations
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Summary:Three sequential efficient glycosylation reactions starting from D‐glucosamine were used in the first total synthesis of Escherichia coli Re lipopolysaccharide, which is one of the most simple lipopolysaccharides found on the surface of living bacteria.
Bibliography:ArticleID:ANIE1475
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istex:7512D44736828FFC71DCE3521E551240DB248E01
This work was supported by the Research for the Future Program (No. 97L00502) from the Japan Society for the Promotion of Science. H.Y. is grateful for a JSPS Research Fellowship for Young Scientists (No. 1241) from the Japan Society for the Promotion of Science. The authors are grateful to Mr. Seiji Adachi for his skillful measurement of NMR spectra.
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ISSN:1433-7851
1521-3773
DOI:10.1002/1521-3773(20010417)40:8<1475::AID-ANIE1475>3.0.CO;2-V