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Literature DB >> 28029240

β-Lactone Synthetase Found in the Olefin Biosynthesis Pathway.

James K Christenson^1,2, Jack E Richman^1,2, Matthew R Jensen^1,2, Jennifer Y Neufeld², Carrie M Wilmot^1,2, Lawrence P Wackett^1,2,3.

Abstract

The first β-lactone synthetase enzyme is reported, creating an unexpected link between the biosynthesis of olefinic hydrocarbons and highly functionalized natural products. The enzyme OleC, involved in the microbial biosynthesis of long-chain olefinic hydrocarbons, reacts with syn- and anti-β-hydroxy acid substrates to yield cis- and trans-β-lactones, respectively. Protein sequence comparisons reveal that enzymes homologous to OleC are encoded in natural product gene clusters that generate β-lactone rings, suggesting a common mechanism of biosynthesis.

Entities: Chemical Disease Gene Species

Mesh：

Substances：

Year: 2017 PMID： 28029240 PMCID： PMC5499249 DOI： 10.1021/acs.biochem.6b01199

Source DB: PubMed Journal: Biochemistry ISSN： 0006-2960 Impact factor: 3.162

14 in total

1. Salinosporamide A: a highly cytotoxic proteasome inhibitor from a novel microbial source, a marine bacterium of the new genus salinospora.

Authors: Robert H Feling; Greg O Buchanan; Tracy J Mincer; Christopher A Kauffman; Paul R Jensen; William Fenical
Journal: Angew Chem Int Ed Engl Date: 2003-01-20 Impact factor: 15.336

2. Functional characterization of an NADPH dependent 2-alkyl-3-ketoalkanoic acid reductase involved in olefin biosynthesis in Stenotrophomonas maltophilia.

Authors: Shilah A Bonnett; Kancharla Papireddy; Samuel Higgins; Stephen del Cardayre; Kevin A Reynolds
Journal: Biochemistry Date: 2011-10-13 Impact factor: 3.162

3. Tylonolide hemiacetal, the aglycone of tylosin, and its partial synthesis.

Authors: S Masamune; Y Hayase; W K Chan; R L Sobzak
Journal: J Am Chem Soc Date: 1976-11-24 Impact factor: 15.419

4. The biochemistry of long-chain, nonisoprenoid hydrocarbons. I. Characterization of the hydrocarbons of Sarcina lutea and the isolation of possible intermediates of biosynthesis.

Authors: P W Albro; J C Dittmer
Journal: Biochemistry Date: 1969-01 Impact factor: 3.162

5. Operon for biosynthesis of lipstatin, the Beta-lactone inhibitor of human pancreatic lipase.

Authors: Tingli Bai; Daozhong Zhang; Shuangjun Lin; Qingshan Long; Yemin Wang; Hongyu Ou; Qianjin Kang; Zixin Deng; Wen Liu; Meifeng Tao
Journal: Appl Environ Microbiol Date: 2014-09-19 Impact factor: 4.792

6. Oxazolomycin biosynthesis in Streptomyces albus JA3453 featuring an "acyltransferase-less" type I polyketide synthase that incorporates two distinct extender units.

Authors: Chunhua Zhao; Jane M Coughlin; Jianhua Ju; Dongqing Zhu; Evelyn Wendt-Pienkowski; Xiufen Zhou; Zhijun Wang; Ben Shen; Zixin Deng
Journal: J Biol Chem Date: 2010-04-20 Impact factor: 5.157

β-Lactone Synthetase Found in the Olefin Biosynthesis Pathway.

1. Salinosporamide A: a highly cytotoxic proteasome inhibitor from a novel microbial source, a marine bacterium of the new genus salinospora.

2. Functional characterization of an NADPH dependent 2-alkyl-3-ketoalkanoic acid reductase involved in olefin biosynthesis in Stenotrophomonas maltophilia.

3. Tylonolide hemiacetal, the aglycone of tylosin, and its partial synthesis.

4. The biochemistry of long-chain, nonisoprenoid hydrocarbons. I. Characterization of the hydrocarbons of Sarcina lutea and the isolation of possible intermediates of biosynthesis.

5. Operon for biosynthesis of lipstatin, the Beta-lactone inhibitor of human pancreatic lipase.

6. Oxazolomycin biosynthesis in Streptomyces albus JA3453 featuring an "acyltransferase-less" type I polyketide synthase that incorporates two distinct extender units.

7. Mining the cinnabaramide biosynthetic pathway to generate novel proteasome inhibitors.

8. Widespread head-to-head hydrocarbon biosynthesis in bacteria and role of OleA.

9. C29 olefinic hydrocarbons biosynthesized by Arthrobacter species.

Review 10. Biosynthesis of oxygen and nitrogen-containing heterocycles in polyketides.

1. β-Lactone formation during product release from a nonribosomal peptide synthetase.

2. Global analysis of adenylate-forming enzymes reveals β-lactone biosynthesis pathway in pathogenic Nocardia.

Review 3. Recent Advances in Enzymatic Complexity Generation: Cyclization Reactions.

4. The role of OleA His285 in orchestration of long-chain acyl-coenzyme A substrates.

5. Active Multienzyme Assemblies for Long-Chain Olefinic Hydrocarbon Biosynthesis.

6. Recombinant Expression and Purification of Large Bacterial Multienzyme Assemblies for Biosynthetic Processes.

7. Novel Electrophilic Scaffold for Imaging of Essential Penicillin-Binding Proteins in Streptococcus pneumoniae.

8. OleA Glu117 is key to condensation of two fatty-acyl coenzyme A substrates in long-chain olefin biosynthesis.

9. Competing off-loading mechanisms of meropenem from an l,d-transpeptidase reduce antibiotic effectiveness.

10. p-Nitrophenyl esters provide new insights and applications for the thiolase enzyme OleA.