Highly diastereoselective construction of L-heptosides by a sequential grignard addition/fleming-tamao oxidation

Maxime Durka; Kevin Buffet; Tianlei Li; Abdellatif Tikad; Bas Hagen; Stéphane P. Vincent

doi:10.1201/b16602

Highly diastereoselective construction of L-heptosides by a sequential grignard addition/fleming-tamao oxidation

Maxime Durka, Kevin Buffet, Tianlei Li, Abdellatif Tikad, Bas Hagen, Stéphane P. Vincent

Research output: Contribution in Book/Catalog/Report/Conference proceeding › Chapter

Abstract

Lipopolysaccharide (LPS) is a key component of the outer membrane of Gramnegative bacteria. This complex molecule plays key roles in the mortality of many infectious diseases as well as in the virulence of numerous human pathogens. LPS consists of three main substructures: lipid A, the oligosaccharide core, and the O-antigen. The oligosaccharide core unit can itself be divided into two parts: the inner core which is formed by at least one molecule of 3-deoxy-α-D-mannooct- 2-ulopyranosonic acid (Kdo) and two molecules of l-glycero-α-D-mannoheptopyranose (l-heptose), and the outer core which is composed of hexoses. The synthesis of heptosides has thus attracted much attention for the synthetic construction of bacterial oligosaccharides, for the preparation of immunogenic glycoconjugates and for the development of novel antibacterial agents.

Original language	English
Title of host publication	Carbohydrate Chemistry
Subtitle of host publication	Proven Synthetic Methods
Editors	Gijsbert Van der Marel, Jeroen Codee
Publisher	CRC Press
Chapter	11
Pages	77-83
Number of pages	7
Volume	2
ISBN (Electronic)	9780429064487
ISBN (Print)	9781439875940
DOIs	https://doi.org/10.1201/b16602
Publication status	Published - 4 Mar 2014

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title = "Highly diastereoselective construction of L-heptosides by a sequential grignard addition/fleming-tamao oxidation",

abstract = "Lipopolysaccharide (LPS) is a key component of the outer membrane of Gramnegative bacteria. This complex molecule plays key roles in the mortality of many infectious diseases as well as in the virulence of numerous human pathogens. LPS consists of three main substructures: lipid A, the oligosaccharide core, and the O-antigen. The oligosaccharide core unit can itself be divided into two parts: the inner core which is formed by at least one molecule of 3-deoxy-α-D-mannooct- 2-ulopyranosonic acid (Kdo) and two molecules of l-glycero-α-D-mannoheptopyranose (l-heptose), and the outer core which is composed of hexoses. The synthesis of heptosides has thus attracted much attention for the synthetic construction of bacterial oligosaccharides, for the preparation of immunogenic glycoconjugates and for the development of novel antibacterial agents.",

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Highly diastereoselective construction of L-heptosides by a sequential grignard addition/fleming-tamao oxidation. / Durka, Maxime; Buffet, Kevin; Li, Tianlei et al.
Carbohydrate Chemistry: Proven Synthetic Methods. ed. / Gijsbert Van der Marel; Jeroen Codee. Vol. 2 CRC Press, 2014. p. 77-83.

Research output: Contribution in Book/Catalog/Report/Conference proceeding › Chapter

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AU - Durka, Maxime

AU - Buffet, Kevin

AU - Li, Tianlei

AU - Tikad, Abdellatif

AU - Hagen, Bas

AU - Vincent, Stéphane P.

PY - 2014/3/4

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N2 - Lipopolysaccharide (LPS) is a key component of the outer membrane of Gramnegative bacteria. This complex molecule plays key roles in the mortality of many infectious diseases as well as in the virulence of numerous human pathogens. LPS consists of three main substructures: lipid A, the oligosaccharide core, and the O-antigen. The oligosaccharide core unit can itself be divided into two parts: the inner core which is formed by at least one molecule of 3-deoxy-α-D-mannooct- 2-ulopyranosonic acid (Kdo) and two molecules of l-glycero-α-D-mannoheptopyranose (l-heptose), and the outer core which is composed of hexoses. The synthesis of heptosides has thus attracted much attention for the synthetic construction of bacterial oligosaccharides, for the preparation of immunogenic glycoconjugates and for the development of novel antibacterial agents.

AB - Lipopolysaccharide (LPS) is a key component of the outer membrane of Gramnegative bacteria. This complex molecule plays key roles in the mortality of many infectious diseases as well as in the virulence of numerous human pathogens. LPS consists of three main substructures: lipid A, the oligosaccharide core, and the O-antigen. The oligosaccharide core unit can itself be divided into two parts: the inner core which is formed by at least one molecule of 3-deoxy-α-D-mannooct- 2-ulopyranosonic acid (Kdo) and two molecules of l-glycero-α-D-mannoheptopyranose (l-heptose), and the outer core which is composed of hexoses. The synthesis of heptosides has thus attracted much attention for the synthetic construction of bacterial oligosaccharides, for the preparation of immunogenic glycoconjugates and for the development of novel antibacterial agents.

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ER -

Highly diastereoselective construction of L-heptosides by a sequential grignard addition/fleming-tamao oxidation

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