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Title

Activated α, β-Unsaturated Aldehydes as Substrate of Dihydroxyacetone Phosphate (DHAP)-Dependent Aldolases in the Context of a Multienzyme System

AuthorsSánchez-Moreno, Israel ; Iturrate Montoya, Laura; Doyagüez, Elisa G.; Martínez, José Antonio; Fernández-Mayoralas, Alfonso ; García-Junceda, Eduardo
KeywordsAldol reaction
Aldolases
Biotransformations
CC bond formation
Multienzyme processes
Issue Date10-Nov-2009
PublisherWiley-VCH
CitationAdvanced Synthesis & Catalysis 351(17): 2967 - 2975(2009)
AbstractThe utility for carbon-carbon bond formation of a multienzyme system composed of recombinant dihydroxyacetone kinase (DHAK) from Citrobacter freundii, the fructose bisphosphate aldolase from rabbit muscle (RAMA) and acetate kinase (AK) for adenosine triphosphate (ATP) regeneration has been studied. Several aldehydes with great structural diversity, including three ,-unsaturated aldehydes, have been analysed as acceptor substrates. It was found that ,-unsaturated aldehydes bearing an electron-withdrawing group in the position to the double bond with a trans configuration are good acceptors for RAMA in this multienzyme system. The aldol reaction proceeds with excellent D-threo enantioselectivity and the aldol adduct is obtained in good overall yield. The L-threo and D-erythro enantiomers are also accessible from rhamnulose 1-phosphate aldolase (Rha-1PA) and fuculose 1-phosphate aldolase (Fuc-1PA) catalysed reactions, respectively.
DescriptionPublished in: Advanced Synthesis & Catalysis, Volume 351, Issue 17, Date: November 2009, Pages: 2967-2975.
Publisher version (URL)http://dx.doi.org/10.1002/adsc.200900603
URIhttp://hdl.handle.net/10261/20183
DOI10.1002/adsc.200900603
ISSN1615-4150
E-ISSN1615-4169
Appears in Collections:(IQOG) Artículos
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