6-Deoxyerythronolide B Synthase Thioesterase-Catalyzed Macrocyclization Is Highly Stereoselective

2012 ◽  
Vol 14 (9) ◽  
pp. 2278-2281 ◽  
Author(s):  
Atahualpa Pinto ◽  
Meng Wang ◽  
Mark Horsman ◽  
Christopher N. Boddy
Keyword(s):  
Deoxyerythronolide B Synthase

scholarly journals Stereospecificity of Ketoreductase Domains of the 6-Deoxyerythronolide B Synthase

2007 ◽  
Vol 129 (44) ◽  
pp. 13758-13769 ◽  
Author(s):  
Roselyne Castonguay ◽  
Weiguo He ◽  
Alice Y. Chen ◽  
Chaitan Khosla ◽  
David E. Cane
Keyword(s):  
Deoxyerythronolide B Synthase

6-Deoxyerythronolide B Synthase 1 Is Specifically Acylated by a Diketide Intermediate at the β-Ketoacyl-Acyl Carrier Protein Synthase Domain of Module 2†

Biochemistry ◽  
1996 ◽  
Vol 35 (48) ◽  
pp. 15244-15248 ◽  
Author(s):  
Naohiro Tsukamoto ◽  
Jo-Anne Chuck ◽  
Guanglin Luo ◽  
Camilla M. Kao ◽  
Chaitan Khosla ◽  
...  
Keyword(s):  
Acyl Carrier Protein ◽  
Carrier Protein ◽  
Deoxyerythronolide B Synthase

scholarly journals Chemobiosynthesis of Novel 6-Deoxyerythronolide B Analogues by Mutation of the Loading Module of 6-Deoxyerythronolide B Synthase 1

2005 ◽  
Vol 71 (8) ◽  
pp. 4503-4509 ◽  
Author(s):  
Sumati Murli ◽  
Karen S. MacMillan ◽  
Zhihao Hu ◽  
Gary W. Ashley ◽  
Steven D. Dong ◽  
...  
Keyword(s):  
Escherichia Coli ◽  
Streptomyces Coelicolor ◽  
Cost Effective ◽  
Effective Alternative ◽  
Facile Synthesis ◽  
E Coli ◽  
Cost Effective Alternative ◽  
Deoxyerythronolide B Synthase

ABSTRACT Chemobiosynthesis (J. R. Jacobsen, C. R. Hutchinson, D. E. Cane, and C. Khosla, Science 277:367-369, 1997) is an important route for the production of polyketide analogues and has been used extensively for the production of analogues of 6-deoxyerythronolide B (6-dEB). Here we describe a new route for chemobiosynthesis using a version of 6-deoxyerythronolide B synthase (DEBS) that lacks the loading module. When the engineered DEBS was expressed in both Escherichia coli and Streptomyces coelicolor and fed a variety of acyl-thioesters, several novel 15-R-6-dEB analogues were produced. The simpler “monoketide” acyl-thioester substrates required for this route of 15-R-6-dEB chemobiosynthesis allow greater flexibility and provide a cost-effective alternative to diketide-thioester feeding to DEBS KS1o for the production of 15-R-6-dEB analogues. Moreover, the facile synthesis of the monoketide acyl-thioesters allowed investigation of alternative thioester carriers. Several alternatives to N-acetyl cysteamine were found to work efficiently, and one of these, methyl thioglycolate, was verified as a productive thioester carrier for mono- and diketide feeding in both E. coli and S. coelicolor.

scholarly journals The 2.7-A crystal structure of a 194-kDa homodimeric fragment of the 6-deoxyerythronolide B synthase

2006 ◽  
Vol 103 (30) ◽  
pp. 11124-11129 ◽  
Author(s):  
Y. Tang ◽  
C.-Y. Kim ◽  
I. I. Mathews ◽  
D. E. Cane ◽  
C. Khosla
Keyword(s):  
Crystal Structure ◽  
Deoxyerythronolide B Synthase

scholarly journals In Vitro Reconstitution and Analysis of the 6-Deoxyerythronolide B Synthase

2013 ◽  
Vol 135 (45) ◽  
pp. 16809-16812 ◽  
Author(s):  
Brian Lowry ◽  
Thomas Robbins ◽  
Chih-Hisang Weng ◽  
Robert V. O’Brien ◽  
David E. Cane ◽  
...  
Keyword(s):  
In Vitro Reconstitution ◽  
Deoxyerythronolide B Synthase
Sign in / Sign up

Export Citation Format

Share Document