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Literature DB >> 29712376

First Total Synthesis of the Re-Type Lipopolysaccharide.

Hiroaki Yoshizaki¹, Naohiro Fukuda¹, Kenjiro Sato¹, Masato Oikawa¹, Koichi Fukase¹, Yasuo Suda¹, Shoichi Kusumoto¹.

Abstract

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.

Entities: Chemical Species

Keywords: glycolipids; glycosylations; lipopolysaccharides; natural products; total synthesis

Year: 2001 PMID： 29712376 DOI： 10.1002/1521-3773(20010417)40:8<1475::AID-ANIE1475>3.0.CO;2-V

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

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Cited

9 in total

1. Enzymatic synthesis of 3-deoxy-d-manno-octulosonic acid (KDO) and its application for LPS assembly.

Authors: Liuqing Wen; Yuan Zheng; Tiehai Li; Peng George Wang
Journal: Bioorg Med Chem Lett Date: 2016-04-21 Impact factor: 2.823

2. Differential induction of innate immune responses by synthetic lipid a derivatives.

Authors: Jidnyasa Gaekwad; Yanghui Zhang; Wei Zhang; Jaxk Reeves; Margreet A Wolfert; Geert-Jan Boons
Journal: J Biol Chem Date: 2010-07-15 Impact factor: 5.157

3. Neisseria meningitidis lipooligosaccharide structure-dependent activation of the macrophage CD14/Toll-like receptor 4 pathway.

Authors: Susu M Zughaier; Yih-Ling Tzeng; Shanta M Zimmer; Anup Datta; Russell W Carlson; David S Stephens
Journal: Infect Immun Date: 2004-01 Impact factor: 3.441

8. Synthesis of a Pentasaccharide Fragment Related to the Inner Core Region of Rhizobial and Agrobacterial Lipopolysaccharides.

Authors: Nino Trattnig; Jean-Baptiste Farcet; Philipp Gritsch; Anna Christler; Ralph Pantophlet; Paul Kosma
Journal: J Org Chem Date: 2017-10-26 Impact factor: 4.354

Review 9. Aminosugar-based immunomodulator lipid A: synthetic approaches.

Authors: Alla Zamyatina
Journal: Beilstein J Org Chem Date: 2018-01-04 Impact factor: 2.883

9 in total

First Total Synthesis of the Re-Type Lipopolysaccharide.

1. Enzymatic synthesis of 3-deoxy-d-manno-octulosonic acid (KDO) and its application for LPS assembly.

2. Differential induction of innate immune responses by synthetic lipid a derivatives.

3. Neisseria meningitidis lipooligosaccharide structure-dependent activation of the macrophage CD14/Toll-like receptor 4 pathway.

4. Progress in Kdo-glycoside chemistry.

5. Synthesis of chlamydia lipopolysaccharide haptens through the use of α-specific 3-iodo-Kdo fluoride glycosyl donors.

6. Scope and Limitations of 3-Iodo-Kdo Fluoride-Based Glycosylation Chemistry using N-Acetyl Glucosamine Acceptors.

7. First and stereoselective synthesis of an α-(2→5)-linked disaccharide of 3-deoxy-D-manno-oct-2-ulosonic acid (Kdo).

8. Synthesis of a Pentasaccharide Fragment Related to the Inner Core Region of Rhizobial and Agrobacterial Lipopolysaccharides.

Review 9. Aminosugar-based immunomodulator lipid A: synthetic approaches.