Identification and stereochemical assignment of the beta-hydroxytryptophan intermediate in the echinomycin biosynthetic pathway

Kento Koketsu; Hiroki Oguri; Kenji Watanabe; Hideaki Oikawa

doi:10.1021/ol061738+

Identification and stereochemical assignment of the beta-hydroxytryptophan intermediate in the echinomycin biosynthetic pathway

Org Lett. 2006 Oct 12;8(21):4719-22. doi: 10.1021/ol061738+.

Authors

Kento Koketsu¹, Hiroki Oguri, Kenji Watanabe, Hideaki Oikawa

Affiliation

¹ Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo 060-0810, Japan.

PMID: 17020286
DOI: 10.1021/ol061738+

Abstract

[reaction: see text] Little is known about how quinoxaline-2-carboxylic acid (QC) is synthesized in nature. On the basis of analysis of echinomycin biosynthetic gene clusters as well as feeding experiments with labeled precursors, we have proposed a biosynthetic pathway to QC and identified the (2S,3S)-beta-hydroxytryptophan as a key intermediate.

Publication types

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

MeSH terms

5-Hydroxytryptophan / chemistry*
Echinomycin / biosynthesis*
Echinomycin / chemistry
Molecular Structure
Quinoxalines / metabolism*
Stereoisomerism
Streptomyces* / enzymology
Streptomyces* / genetics
Streptomyces* / metabolism

Substances

Quinoxalines
Echinomycin
5-Hydroxytryptophan
quinoxaline-2-carboxylic acid