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Title: Application of an Acyl-CoA Ligase from Streptomyces aizunensis for Lactam Biosynthesis

ε-Caprolactam and δ-valerolactam are important commodity chemicals used in the manufacture of nylons, with millions of tons produced annually. Biological production of these highly valued chemicals has been limited due to a lack of enzymes that cyclize ω-amino fatty acid precursors to corresponding lactams under ambient conditions. In this study, we demonstrated production of these chemicals using ORF26, an acyl-CoA ligase involved in the biosynthesis of ECO-02301 in Streptomyces aizunensis. This enzyme has a broad substrate spectrum and can cyclize 4-aminobutyric acid into γ-butyrolactam, 5-aminovaleric acid into δ-valerolactam and 6-aminocaproic acid into ε-caprolactam. Recombinant E. coli expressing ORF26 produced valerolactam and caprolactam when 5-aminovaleric acid and 6-aminocaproic acid were added to the culture medium. Upon coexpressing ORF26 with a metabolic pathway that produced 5-aminovaleric acid from lysine, we were able to demonstrate production of δ-valerolactam from lysine.
Authors:
 [1] ;  [2] ;  [2] ;  [2] ;  [2] ; ORCiD logo [3]
  1. Univ. of California, Berkeley, CA (United States); Joint BioEnergy Inst. (JBEI), Emeryville, CA (United States)
  2. Joint BioEnergy Inst. (JBEI), Emeryville, CA (United States)
  3. Univ. of California, Berkeley, CA (United States); Joint BioEnergy Inst. (JBEI), Emeryville, CA (United States); Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States); Technical Univ. of Denmark, Horsholm (Denmark)
Publication Date:
Grant/Contract Number:
AC02-05CH11231; EEC 0540879
Type:
Accepted Manuscript
Journal Name:
ACS Synthetic Biology
Additional Journal Information:
Journal Volume: 6; Journal Issue: 5; Journal ID: ISSN 2161-5063
Publisher:
American Chemical Society (ACS)
Research Org:
Joint BioEnergy Inst. (JBEI), Emeryville, CA (United States); Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
Sponsoring Org:
USDOE Office of Science (SC), Biological and Environmental Research (BER) (SC-23); National Science Foundation (NSF)
Country of Publication:
United States
Language:
English
Subject:
59 BASIC BIOLOGICAL SCIENCES; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
OSTI Identifier:
1379853

Zhang, Jingwei, Barajas, Jesus F., Burdu, Mehmet, Wang, George, Baidoo, Edward E., and Keasling, Jay D.. Application of an Acyl-CoA Ligase from Streptomyces aizunensis for Lactam Biosynthesis. United States: N. p., Web. doi:10.1021/acssynbio.6b00372.
Zhang, Jingwei, Barajas, Jesus F., Burdu, Mehmet, Wang, George, Baidoo, Edward E., & Keasling, Jay D.. Application of an Acyl-CoA Ligase from Streptomyces aizunensis for Lactam Biosynthesis. United States. doi:10.1021/acssynbio.6b00372.
Zhang, Jingwei, Barajas, Jesus F., Burdu, Mehmet, Wang, George, Baidoo, Edward E., and Keasling, Jay D.. 2017. "Application of an Acyl-CoA Ligase from Streptomyces aizunensis for Lactam Biosynthesis". United States. doi:10.1021/acssynbio.6b00372. https://www.osti.gov/servlets/purl/1379853.
@article{osti_1379853,
title = {Application of an Acyl-CoA Ligase from Streptomyces aizunensis for Lactam Biosynthesis},
author = {Zhang, Jingwei and Barajas, Jesus F. and Burdu, Mehmet and Wang, George and Baidoo, Edward E. and Keasling, Jay D.},
abstractNote = {ε-Caprolactam and δ-valerolactam are important commodity chemicals used in the manufacture of nylons, with millions of tons produced annually. Biological production of these highly valued chemicals has been limited due to a lack of enzymes that cyclize ω-amino fatty acid precursors to corresponding lactams under ambient conditions. In this study, we demonstrated production of these chemicals using ORF26, an acyl-CoA ligase involved in the biosynthesis of ECO-02301 in Streptomyces aizunensis. This enzyme has a broad substrate spectrum and can cyclize 4-aminobutyric acid into γ-butyrolactam, 5-aminovaleric acid into δ-valerolactam and 6-aminocaproic acid into ε-caprolactam. Recombinant E. coli expressing ORF26 produced valerolactam and caprolactam when 5-aminovaleric acid and 6-aminocaproic acid were added to the culture medium. Upon coexpressing ORF26 with a metabolic pathway that produced 5-aminovaleric acid from lysine, we were able to demonstrate production of δ-valerolactam from lysine.},
doi = {10.1021/acssynbio.6b00372},
journal = {ACS Synthetic Biology},
number = 5,
volume = 6,
place = {United States},
year = {2017},
month = {4}
}