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

doi:10.1016/S0040-4039(98)01301-X

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

Université de Strasbourg
University of Barcelona

Research output: Contribution to journal › Article › peer-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 language	English
Pages (from-to)	6185-6188
Number of pages	4
Journal	Tetrahedron Letters
Volume	39
Issue number	34
DOIs	https://doi.org/10.1016/S0040-4039(98)01301-X
Publication status	Published - 20 Aug 1998
Externally published	Yes

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10.1016/S0040-4039(98)01301-X

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

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.",

author = "Putra, \{Surya Rosa\} and Lionel Charon and Knut Danielsen and Catherine Pale-Grosdemange and Lois, \{Luisa Maria\} and Narciso Campos and Albert Boronat and Michel Rohmer",

year = "1998",

month = aug,

day = "20",

doi = "10.1016/S0040-4039(98)01301-X",

language = "English",

volume = "39",

pages = "6185--6188",

journal = "Tetrahedron Letters",

issn = "0040-4039",

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TY - JOUR

T1 - 5-hydroxypentane-2,3-dione (Laurencione), a bacterial metabolite of 1- deoxy-D-threo-pentulose

AU - Putra, Surya Rosa

AU - Charon, Lionel

AU - Danielsen, Knut

AU - Pale-Grosdemange, Catherine

AU - Lois, Luisa Maria

AU - Campos, Narciso

AU - Boronat, Albert

AU - Rohmer, Michel

PY - 1998/8/20

Y1 - 1998/8/20

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/0032552065

U2 - 10.1016/S0040-4039(98)01301-X

DO - 10.1016/S0040-4039(98)01301-X

M3 - Article

AN - SCOPUS:0032552065

SN - 0040-4039

VL - 39

SP - 6185

EP - 6188

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 34

ER -

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

Abstract

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