title: Identification and stereochemical assignment of the beta-hydroxytryptophan intermediate in the echinomycin biosynthetic pathway.
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.
authors.affiliation: Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo 060-0810, Japan.
authors.forename: Kento
authors.initials: K
authors.lastname: Koketsu
authors.forename: Hiroki
authors.initials: H
authors.lastname: Oguri
authors.forename: Kenji
authors.initials: K
authors.lastname: Watanabe
authors.forename: Hideaki
authors.initials: H
authors.lastname: Oikawa
mesh_terms: D006916:5-Hydroxytryptophan / Q000737:chemistry*; D004448:Echinomycin / Q000096:biosynthesis* / Q000737:chemistry; D015394:Molecular Structure; D011810:Quinoxalines / Q000378:metabolism*; D013237:Stereoisomerism; D013302:Streptomyces / Q000201:enzymology / Q000235:genetics / Q000378:metabolism
chemical_list: D011810:Quinoxalines; D004448:Echinomycin; D006916:5-Hydroxytryptophan; C042218:quinoxaline-2-carboxylic acid