β-Lactone Synthetase Found in the Olefin Biosynthesis Pathway

被引:39
作者
Christenson, James K. [1 ,2 ]
Richman, Jack E. [1 ,2 ]
Jensen, Matthew R. [1 ,2 ]
Neufeld, Jennifer Y. [2 ]
Wilmot, Carrie M. [1 ,2 ]
Wackett, Lawrence P. [1 ,2 ,3 ]
机构
[1] Univ Minnesota, Dept Biochem Mol Biol & Biophys, Minneapolis, MN 55455 USA
[2] Univ Minnesota, Inst Biotechnol, St Paul, MN 55108 USA
[3] Univ Minnesota, Microbial & Plant Genom Inst, St Paul, MN 55108 USA
基金
美国国家卫生研究院;
关键词
HYDROCARBONS; PROTEASOME; INHIBITOR;
D O I
10.1021/acs.biochem.6b01199
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The first beta-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-beta-hydroxy acid substrates to yield cis- and trans-beta-lactones, respectively. Protein sequence comparisons reveal that enzymes homologous to OleC are encoded in natural product gene clusters that generate beta-lactone rings, suggesting a common mechanism of biosynthesis.
引用
收藏
页码:348 / 351
页数:4
相关论文
共 19 条
  • [1] BIOCHEMISTRY OF LONG-CHAIN NONISOPRENOID HYDROCARBONS .I. CHARACTERIZATION OF HYDROCARBONS OF SARCINA LUTEA AND ISOLATION OF POSSIBLE INTERMEDIATES OF BIOSYNTHESIS
    ALBRO, PW
    DITTMER, JC
    [J]. BIOCHEMISTRY, 1969, 8 (01) : 394 - &
  • [2] Operon for Biosynthesis of Lipstatin, the Beta-Lactone Inhibitor of Human Pancreatic Lipase
    Bai, Tingli
    Zhang, Daozhong
    Lin, Shuangjun
    Long, Qingshan
    Wang, Yemin
    Ou, Hongyu
    Kang, Qianjin
    Deng, Zixin
    Liu, Wen
    Tao, Meifeng
    [J]. APPLIED AND ENVIRONMENTAL MICROBIOLOGY, 2014, 80 (24) : 7473 - 7483
  • [3] Functional Characterization of an NADPH Dependent 2-Alkyl-3-ketoalkanoic Acid Reductase Involved in Olefin Biosynthesis in Stenotrophomonas maltophilia
    Bonnett, Shilah A.
    Papireddy, Kancharla
    Higgins, Samuel
    del Cardayre, Stephen
    Reynolds, Kevin A.
    [J]. BIOCHEMISTRY, 2011, 50 (44) : 9633 - 9640
  • [4] Crystal structure of firefly luciferase throws light on a superfamily of adenylate-forming enzymes
    Conti, E
    Franks, NP
    Brick, P
    [J]. STRUCTURE, 1996, 4 (03) : 287 - 298
  • [5] Mechanistic studies on the inactivation of the proteasome by lactacystin A central role for clasto-lactacystin beta-lactone
    Dick, LR
    Cruikshank, AA
    Grenier, L
    Melandri, FD
    Nunes, SL
    Stein, RL
    [J]. JOURNAL OF BIOLOGICAL CHEMISTRY, 1996, 271 (13) : 7273 - 7276
  • [6] Salinosporamide A:: A highly cytotoxic proteasome inhibitor from a novel microbial source, a marine bacterium of the new genus Salinospora
    Feling, RH
    Buchanan, GO
    Mincer, TJ
    Kauffman, CA
    Jensen, PR
    Fenical, W
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (03) : 355 - +
  • [7] Purification and Characterization of OleA from Xanthomonas campestris and Demonstration of a Non-decarboxylative Claisen Condensation Reaction
    Frias, Janice A.
    Richman, Jack E.
    Erickson, Jasmine S.
    Wackett, Lawrence P.
    [J]. JOURNAL OF BIOLOGICAL CHEMISTRY, 2011, 286 (13) : 10930 - 10938
  • [8] C29 Olefinic Hydrocarbons Biosynthesized by Arthrobacter Species
    Frias, Janice A.
    Richman, Jack E.
    Wackett, Lawrence P.
    [J]. APPLIED AND ENVIRONMENTAL MICROBIOLOGY, 2009, 75 (06) : 1774 - 1777
  • [9] Biosynthesis of oxygen and nitrogen-containing heterocycles in polyketides
    Hemmerling, Franziska
    Hahn, Frank
    [J]. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2016, 12 : 1512 - 1550
  • [10] Stenotrophomonas maltophilia OleC-Catalyzed ATP-Dependent Formation of Long-Chain Z-Olefins from 2-Alkyl-3-hydroxyalkanoic Acids
    Kancharla, Papireddy
    Bonnett, Shilah A.
    Reynolds, Kevin A.
    [J]. CHEMBIOCHEM, 2016, 17 (15) : 1426 - 1429