Synthesis of D-glycero-D-manno-heptose 1,7-bisphosphate (HBP) featuring a β-stereoselective bis-phosphorylation

Lina Liang; Stéphane P. Vincent

doi:10.1016/j.tetlet.2017.08.005

Synthesis of D-glycero-D-manno-heptose 1,7-bisphosphate (HBP) featuring a β-stereoselective bis-phosphorylation

Lina Liang, Stéphane P. Vincent

Unit of organic chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

D-glycero-D-manno-Heptose 1,7-bisphosphate (HBP) plays a unique role in bacteriology. We describe in this study a very efficient synthesis of HBP, featuring a highly 6-D-selective construction of the heptose scaffold as well as a double phosphorylation step installing, in a single operation and in a β-stereoselective manner, the 1- and the 7-phosphates.

Original language	English
Pages (from-to)	3631-3633
Number of pages	3
Journal	Tetrahedron Letters
Volume	58
Issue number	37
DOIs	https://doi.org/10.1016/j.tetlet.2017.08.005
Publication status	Published - 13 Sept 2017

Keywords

Bacterial saccharides
Carbohydrates
Glycosidation
Phosphorylation

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10.1016/j.tetlet.2017.08.005

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title = "Synthesis of D-glycero-D-manno-heptose 1,7-bisphosphate (HBP) featuring a β-stereoselective bis-phosphorylation",

abstract = "D-glycero-D-manno-Heptose 1,7-bisphosphate (HBP) plays a unique role in bacteriology. We describe in this study a very efficient synthesis of HBP, featuring a highly 6-D-selective construction of the heptose scaffold as well as a double phosphorylation step installing, in a single operation and in a β-stereoselective manner, the 1- and the 7-phosphates.",

keywords = "Bacterial saccharides, Carbohydrates, Glycosidation, Phosphorylation",

author = "Lina Liang and Vincent, {St{\'e}phane P.}",

note = "Funding Information: The authors thank the China Scholarship Council (CSC, PhD grant n? 201506670006 to L.L.). Publisher Copyright: {\textcopyright} 2017 Elsevier Ltd Copyright: Copyright 2017 Elsevier B.V., All rights reserved.",

year = "2017",

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doi = "10.1016/j.tetlet.2017.08.005",

language = "English",

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journal = "Tetrahedron Letters",

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AU - Liang, Lina

AU - Vincent, Stéphane P.

N1 - Funding Information: The authors thank the China Scholarship Council (CSC, PhD grant n? 201506670006 to L.L.). Publisher Copyright: © 2017 Elsevier Ltd Copyright: Copyright 2017 Elsevier B.V., All rights reserved.

PY - 2017/9/13

Y1 - 2017/9/13

N2 - D-glycero-D-manno-Heptose 1,7-bisphosphate (HBP) plays a unique role in bacteriology. We describe in this study a very efficient synthesis of HBP, featuring a highly 6-D-selective construction of the heptose scaffold as well as a double phosphorylation step installing, in a single operation and in a β-stereoselective manner, the 1- and the 7-phosphates.

AB - D-glycero-D-manno-Heptose 1,7-bisphosphate (HBP) plays a unique role in bacteriology. We describe in this study a very efficient synthesis of HBP, featuring a highly 6-D-selective construction of the heptose scaffold as well as a double phosphorylation step installing, in a single operation and in a β-stereoselective manner, the 1- and the 7-phosphates.

KW - Bacterial saccharides

KW - Carbohydrates

KW - Glycosidation

KW - Phosphorylation

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DO - 10.1016/j.tetlet.2017.08.005

M3 - Article

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SN - 0040-4039

VL - 58

SP - 3631

EP - 3633

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 37

ER -

Synthesis of D-glycero-D-manno-heptose 1,7-bisphosphate (HBP) featuring a β-stereoselective bis-phosphorylation

Abstract

Keywords

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