Literature DB >> 23102024

Baeyer-Villiger C-C bond cleavage reaction in gilvocarcin and jadomycin biosynthesis.

Nidhi Tibrewal1, Pallab Pahari, Guojun Wang, Madan K Kharel, Caleb Morris, Theresa Downey, Yanpeng Hou, Tim S Bugni, Jürgen Rohr.   

Abstract

GilOII has been unambiguously identified as the key enzyme performing the crucial C-C bond cleavage reaction responsible for the unique rearrangement of a benz[a]anthracene skeleton to the benzo[d]naphthopyranone backbone typical of the gilvocarcin-type natural anticancer antibiotics. Further investigations of this enzyme led to the isolation of a hydroxyoxepinone intermediate, leading to important conclusions regarding the cleavage mechanism.

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Year:  2012        PMID: 23102024      PMCID: PMC3498853          DOI: 10.1021/ja3081154

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  21 in total

1.  Characterization of JadH as an FAD- and NAD(P)H-dependent bifunctional hydroxylase/dehydrase in jadomycin biosynthesis.

Authors:  Yihua Chen; Keqiang Fan; Yongzhi He; Xinping Xu; Yanfeng Peng; Tingting Yu; Cuijuan Jia; Keqian Yang
Journal:  Chembiochem       Date:  2010-05-17       Impact factor: 3.164

2.  Identification of the product of toxoflavin lyase: degradation via a Baeyer-Villiger oxidation.

Authors:  Benjamin Philmus; Sameh Abdelwahed; Howard J Williams; Michael K Fenwick; Steven E Ealick; Tadhg P Begley
Journal:  J Am Chem Soc       Date:  2012-03-09       Impact factor: 15.419

3.  Total synthesis of jadomycin A and a carbasugar analogue of jadomycin B.

Authors:  Mingde Shan; Ehesan U Sharif; George A O'Doherty
Journal:  Angew Chem Int Ed Engl       Date:  2010-12-03       Impact factor: 15.336

4.  Multi-oxygenase complexes of the gilvocarcin and jadomycin biosyntheses.

Authors:  Madan K Kharel; Lili Zhu; Tao Liu; Jürgen Rohr
Journal:  J Am Chem Soc       Date:  2007-03-09       Impact factor: 15.419

5.  Roles of the synergistic reductive O-methyltransferase GilM and of O-methyltransferase GilMT in the gilvocarcin biosynthetic pathway.

Authors:  Nidhi Tibrewal; Theresa E Downey; Steven G Van Lanen; Ehesan Ul Sharif; George A O'Doherty; Jürgen Rohr
Journal:  J Am Chem Soc       Date:  2012-07-19       Impact factor: 15.419

6.  Enzymatic total synthesis of defucogilvocarcin M and its implications for gilvocarcin biosynthesis.

Authors:  Pallab Pahari; Madan K Kharel; Micah D Shepherd; Steven G van Lanen; Jürgen Rohr
Journal:  Angew Chem Int Ed Engl       Date:  2011-12-23       Impact factor: 15.336

7.  GilR, an unusual lactone-forming enzyme involved in gilvocarcin biosynthesis.

Authors:  Madan Kumar Kharel; Pallab Pahari; Hui Lian; Jürgen Rohr
Journal:  Chembiochem       Date:  2009-05-25       Impact factor: 3.164

8.  Gilvocarcins, new antitumor antibiotics. 1. Taxonomy, fermentation, isolation and biological activities.

Authors:  H Nakano; Y Matsuda; K Ito; S Ohkubo; M Morimoto; F Tomita
Journal:  J Antibiot (Tokyo)       Date:  1981-03       Impact factor: 2.649

9.  Genome mining in Streptomyces avermitilis: A biochemical Baeyer-Villiger reaction and discovery of a new branch of the pentalenolactone family tree.

Authors:  Jiaoyang Jiang; Charles N Tetzlaff; Satoshi Takamatsu; Masato Iwatsuki; Mamoru Komatsu; Haruo Ikeda; David E Cane
Journal:  Biochemistry       Date:  2009-07-14       Impact factor: 3.162

10.  Crystal structure of Baeyer-Villiger monooxygenase MtmOIV, the key enzyme of the mithramycin biosynthetic pathway .

Authors:  Miranda P Beam; Mary A Bosserman; Nicholas Noinaj; Marie Wehenkel; Jürgen Rohr
Journal:  Biochemistry       Date:  2009-06-02       Impact factor: 3.162

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  18 in total

1.  Molecular insight into substrate recognition and catalysis of Baeyer-Villiger monooxygenase MtmOIV, the key frame-modifying enzyme in the biosynthesis of anticancer agent mithramycin.

Authors:  Mary A Bosserman; Theresa Downey; Nicholas Noinaj; Susan K Buchanan; Jürgen Rohr
Journal:  ACS Chem Biol       Date:  2013-09-13       Impact factor: 5.100

2.  Formation of an Angular Aromatic Polyketide from a Linear Anthrene Precursor via Oxidative Rearrangement.

Authors:  Guixi Gao; Xiangyang Liu; Min Xu; Yemin Wang; Fei Zhang; Lijun Xu; Jin Lv; Qingshan Long; Qianjin Kang; Hong-Yu Ou; Ying Wang; Jürgen Rohr; Zixin Deng; Ming Jiang; Shuangjun Lin; Meifeng Tao
Journal:  Cell Chem Biol       Date:  2017-07-14       Impact factor: 8.116

3.  Production of Stealthin C Involves an S-N-Type Smiles Rearrangement.

Authors:  Peng Wang; Gloria J Hong; Matthew R Wilson; Emily P Balskus
Journal:  J Am Chem Soc       Date:  2017-02-16       Impact factor: 15.419

Review 4.  Oxidative Cyclization in Natural Product Biosynthesis.

Authors:  Man-Cheng Tang; Yi Zou; Kenji Watanabe; Christopher T Walsh; Yi Tang
Journal:  Chem Rev       Date:  2016-12-12       Impact factor: 60.622

5.  Discovery of the lomaiviticin biosynthetic gene cluster in Salinispora pacifica.

Authors:  Jeffrey E Janso; Brad A Haltli; Alessandra S Eustáquio; Kerry Kulowski; Abraham J Waldman; Li Zha; Hitomi Nakamura; Valerie S Bernan; Haiyin He; Guy T Carter; Frank E Koehn; Emily P Balskus
Journal:  Tetrahedron       Date:  2014-07-08       Impact factor: 2.457

6.  Biosynthesis: A carbonate architect emerges.

Authors:  Yuhui Sun
Journal:  Nat Chem Biol       Date:  2014-05-18       Impact factor: 15.040

Review 7.  The Enzymology of Organic Transformations: A Survey of Name Reactions in Biological Systems.

Authors:  Chia-I Lin; Reid M McCarty; Hung-Wen Liu
Journal:  Angew Chem Int Ed Engl       Date:  2017-02-14       Impact factor: 15.336

8.  General and practical carboxyl-group-directed remote C-H oxygenation reactions of arenes.

Authors:  Yang Wang; Anton V Gulevich; Vladimir Gevorgyan
Journal:  Chemistry       Date:  2013-10-21       Impact factor: 5.236

9.  Dynamic regulation of Monascus azaphilones biosynthesis by the binary MrPigE-MrPigF oxidoreductase system.

Authors:  Yali Duan; Hongmin Ma; Xuetuan Wei; Mu Li
Journal:  Appl Microbiol Biotechnol       Date:  2022-10-12       Impact factor: 5.560

10.  Spliceostatin hemiketal biosynthesis in Burkholderia spp. is catalyzed by an iron/α-ketoglutarate-dependent dioxygenase.

Authors:  Alessandra S Eustáquio; Jeffrey E Janso; Anokha S Ratnayake; Christopher J O'Donnell; Frank E Koehn
Journal:  Proc Natl Acad Sci U S A       Date:  2014-08-05       Impact factor: 11.205

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