5-hydroxypentane-2,3-dione (Laurencione), a bacterial metabolite of 1- deoxy-D-threo-pentulose

Surya Rosa Putra, Lionel Charon, Knut Danielsen, Catherine Pale-Grosdemange, Luisa Maria Lois, Narciso Campos, Albert Boronat, Michel Rohmer*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)

Abstract

Cell-free systems from the bacteria Escherichia coli and Klebsiella planticola that were incubated with 13C labeled pyruvate and D- glyceraldehyde synthesized 5-hydroxypentane-2,3-dione (laurencione) along with 1-deoxy-D-threo-pentulose (1-deoxy-D-xylulose). Both compounds showed identical labeling patterns, indicating that the C5 skeletons were derived from the condensation of (hydroxyethyl)thiamin on D-glyceraldehyde. Conversion of [5,5-2H2]deoxyxylulose into laurencione by a cell-free system from E. coli showed that the α-dione is obtained from the pentulose by water elimination.

Original languageEnglish
Pages (from-to)6185-6188
Number of pages4
JournalTetrahedron Letters
Volume39
Issue number34
DOIs
Publication statusPublished - 20 Aug 1998
Externally publishedYes

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