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

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 p...

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Detalhes bibliográficos
Autores: Putra, Surya Rosa, Charon, Lionel, Danielsen, Knut, Pale Grosdemange, Catherine, Lois Rojas, Luisa María, Campos Martínez, Narciso, Boronat i Margosa, Albert, Rohmer, Michel
Formato: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:1998
País:España
Recursos:Universidad de Barcelona
Repositorio:Dipòsit Digital de la UB
OAI Identifier:oai:diposit.ub.edu:2445/225941
Acesso em linha:https://hdl.handle.net/2445/225941
Access Level:acceso abierto
Palavra-chave:Química microbiològica
Química bioinorgànica
Microbiological chemistry
Bioinorganic chemistry
Descrição
Resumo: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.