Genetic Engineering of Streptomyces coelicolor A3(2) for the Enantioselective Reduction of Unnatural beta-Keto-Ester Substrates.

Potential "reagents" for the enantioselective reduction, and other biotransformations, of beta-keto-esters result from the genetic engineering of Streptomyces coelicolor A3(2). For example, incubation of the N-acetylcysteamine thioester 1 with the recombinant strain CH999/pIJ5675 followed by treatment with MeOH/HCl gave the lactone 2 as essentially a single enantiomer.

[1]  D. Hopwood,et al.  Proof that the ACTVI genetic region of Streptomyces coelicolor A3(2) is involved in stereospecific pyran ring formation in the biosynthesis of actinorhodin. , 1999, Bioorganic & medicinal chemistry letters.

[2]  D. Hopwood,et al.  Genetic Contributions to Understanding Polyketide Synthases. , 1997, Chemical reviews.

[3]  J R Jacobsen,et al.  Precursor-directed biosynthesis of erythromycin analogs by an engineered polyketide synthase. , 1997, Science.

[4]  I. Gilbert,et al.  Synthesis of β-keto and α,β-unsaturated N-acetylcysteamine thioesters , 1995 .

[5]  S. Roelens,et al.  A protocol for the efficient synthesis of enantiopure .beta.-substituted .beta.-lactones , 1993 .

[6]  D. Cane,et al.  Macrolide biosynthesis. 6 Mechanism of polyketide chain elongation , 1991 .

[7]  P. Bartel,et al.  Biosynthesis of anthraquinones by interspecies cloning of actinorhodin biosynthesis genes in streptomycetes: clarification of actinorhodin gene functions , 1990, Journal of bacteriology.

[8]  J. Staunton,et al.  Aspyrone biosynthesis in Aspergillus melleus: identification of the intermediates formed on the polyketide synthase (PKS) in the first chain extension cycle leading to crotonate , 1991 .

[9]  S. Servi.  Baker's Yeast as a Reagent in Organic Synthesis , 1990 .

[10]  M. Yamaguchi,et al.  A synthesis of polycyclic aromatic compounds by the calcium acetate-induced aromatization of polyoxoalkanedioates generated from diesters and acetoacetate dianion , 1990 .

[11]  S. Masamune,et al.  C-Acylierung unter praktisch neutralen Bedingungen† , 1979 .

[12]  W. Maier,et al.  General Synthesis of Potentially Antiviral α‐Adamantyl Carbonyl Compounds , 1979 .