Stereoselective synthesis of <scp>d</scp>-<i>glycero</i>-<scp>d</scp>-<i>manno</i>-heptose-1β,7-bisphosphate (HBP) from <scp>d</scp>-mannurono-2,6-lactone-Reference-Cited by-同舟云学术

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Stereoselective synthesis of d-glycero-d-manno-heptose-1β,7-bisphosphate (HBP) from d-mannurono-2,6-lactone

Published:2024 Issue:13 Volume:22 Page:2544-2548
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

Shinotsuka Yuta¹,Nakajima Riko¹,Ogawa Kohei¹,Takise Kaede¹,Takeuchi Yutaka²,Tanaka Hiroshi²^ORCID,Sasaki Kaname¹^ORCID

Affiliation:

1. Department of Chemistry, Toho University, 2-2-1 Miyama, Funabashi 274-8510, Japan

2. Department of Chemical Science and Engineering, Tokyo Institute of Technology, 2-12-1-H101, Ookayama, Muguro-ku, Tokyo 152-8552, Japan

Abstract

The synthesis of HBP is distinguished by the β-steroselective glycosylation of phosphate and ketone formation from the 2,6-lactone through the utilization of a C1 nucleophile.

Funder

Japan Society for the Promotion of Science

Publisher

Royal Society of Chemistry (RSC)

Link

http://pubs.rsc.org/en/content/articlepdf/2024/OB/D4OB00139G

Reference29 articles.

1. Lipopolysaccharide modification in Gram-negative bacteria during chronic infection

2. Divergence of Biochemical Function in the HAD Superfamily: d-glycero-d-manno-Heptose-1,7-bisphosphate Phosphatase (GmhB)

3. Novel pathways for biosynthesis of nucleotide-activated glycero-manno-heptose precursors of bacterial glycoproteins and cell surface polysaccharides

4. Cytosolic detection of the bacterial metabolite HBP activates TIFA-dependent innate immunity

5. Alpha-kinase 1 is a cytosolic innate immune receptor for bacterial ADP-heptose

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