Determination of the stereochemistry of 2-succinyl-5-enolpyruvyl-6-hydroxy-3- cyclohexene-1-carboxylate, a key intermediate in menaquinone biosynthesis

Ming Jiang; Minjiao Chen; Yang Cao; Yinhua Yang; Kong Hung Sze; Xiaolei Chen; Zhihong Guo

doi:10.1021/ol702126m

Determination of the stereochemistry of 2-succinyl-5-enolpyruvyl-6-hydroxy-3- cyclohexene-1-carboxylate, a key intermediate in menaquinone biosynthesis

Org Lett. 2007 Nov 8;9(23):4765-7. doi: 10.1021/ol702126m. Epub 2007 Oct 23.

Authors

Ming Jiang¹, Minjiao Chen, Yang Cao, Yinhua Yang, Kong Hung Sze, Xiaolei Chen, Zhihong Guo

Affiliation

¹ Department of Chemistry, Center for Cancer Research, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR, China.

PMID: 17956107
DOI: 10.1021/ol702126m

Abstract

The turnover product of the committed step of menaquinone biosynthesis was isolated and determined to be (1R,2S,5S,6S)-2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate. Structural determination of this key intermediate represents a critical step to complete elucidation of the biosynthetic pathway.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Chorismic Acid / chemistry
Cyclohexanecarboxylic Acids / chemical synthesis
Cyclohexanecarboxylic Acids / chemistry*
Cyclohexenes / chemistry
Keto Acids / chemical synthesis
Keto Acids / chemistry*
Magnetic Resonance Spectroscopy
Models, Molecular
Molecular Structure
Protons
Stereoisomerism
Vitamin K 2 / chemistry*
Vitamin K 2 / metabolism*

Substances

2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylic acid
Cyclohexanecarboxylic Acids
Cyclohexenes
Keto Acids
Protons
Vitamin K 2
isochorismic acid
Chorismic Acid