期刊
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC
卷 64, 期 1-2, 页码 113-117出版社
ELSEVIER SCIENCE BV
DOI: 10.1016/j.molcatb.2010.03.001
关键词
Acetylacetoin synthase; Bacillus stearothermophilus; C-C bond formation; Enzyme catalysis; alpha-Hydroxy-1,3-diketones
The synthesis of alpha-hydroxy-1,3-diketones 2 and 3 from the corresponding 1,2-diketones with Bacillus stearothermophilus ATCC2027 acetylacetoin synthase (AAS) was described. The enzyme catalyzed the condensation of the dialkyl- or alkyl-aryl-1,2-diketones 1 with the elimination of a carboxylic acid moiety. The reactions were carried out using either one diketone both acting as donor and acceptor (homo-coupling) or with two different reacting species (cross-coupling). The homo-coupling reactions of the asymmetric dialkyl-1,2-diketones 1c-d afforded a mixture of the regioisomers 2 (30-42%, ee 67-70%) and 3 (19-25%), while only the 1,3-diketones 2a (57%), 2b (60%), and 2e (45%, ee 76%) were obtained using 2,3-butanedione 1a, 3,4-hexanedione 1b, and 1-phenyl-1,2-propanedione 1e, respectively. The cross-coupling reactions of the diketones 1a and 1b, and 1b and 1e were carried out using various ratios of the donor and the acceptor. In both cases the only cross-coupling product was 3-ethyl-3-hydroxy-2,4-hexanedione 4(62%, ee 91%). (C) 2010 Elsevier B.V. All rights reserved.
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