Literature DB >> 29935040

Total Synthesis Establishes the Biosynthetic Pathway to the Naphterpin and Marinone Natural Products.

Lauren A M Murray1, Shaun M K McKinnie2,3, Henry P Pepper1, Reto Erni2,3, Zachary D Miles2,3, Michelle C Cruickshank1, Borja López-Pérez1, Bradley S Moore2,3, Jonathan H George1.   

Abstract

The naphterpins and marinones are naphthoquinone meroterpenoids with an unusual aromatic oxidation pattern that is biosynthesized from 1,3,6,8-tetrahydroxynaphthalene (THN). We propose that cryptic halogenation of THN derivatives by vanadium-dependent chloroperoxidase (VCPO) enzymes is key to this biosynthetic pathway, despite the absence of chlorine in these natural products. This speculation inspired a total synthesis to mimic the naphterpin/marinone biosynthetic pathway. In validation of this biogenetic hypothesis, two VCPOs were discovered that interconvert several of the proposed biosynthetic intermediates.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  biomimetic synthesis; biosynthesis; dearomatization; meroterpenoids; total synthesis

Mesh：

Substances：

Year:  2018        PMID： 29935040      PMCID： PMC6248334          DOI： 10.1002/anie.201804351

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  36 in total

1.  Studies on terpenoids produced by actinomycetes. Isolation and structural elucidation of antioxidative agents, naphterpins B and C.

Authors:  Hiroshi Takagi; Keiichiro Motohashi; Toru Miyamoto; Kazuo Shin-ya; Kazuo Furihata; Haruo Seto
Journal:  J Antibiot (Tokyo)       Date:  2005-04       Impact factor: 2.649

Review 2.  Exploring the chemistry and biology of vanadium-dependent haloperoxidases.

Authors:  Jaclyn M Winter; Bradley S Moore
Journal:  J Biol Chem       Date:  2009-04-10       Impact factor: 5.157

3.  Metabolic products of microorganisms, 260. Naphthgeranines, new naphthoquinone antibiotics from Streptomyces sp.

Authors:  P Wessels; A Göhrt; A Zeeck; H Drautz; H Zähner
Journal:  J Antibiot (Tokyo)       Date:  1991-09       Impact factor: 2.649

4.  Chemically unprecedented biocatalytic (AuaG) retro-[2,3]-Wittig rearrangement: a new insight into aurachin B biosynthesis.

Authors:  Yohei Katsuyama; Xu-Wen Li; Rolf Müller; Bastien Nay
Journal:  Chembiochem       Date:  2014-09-10       Impact factor: 3.164

5.  Merochlorins A-D, cyclic meroterpenoid antibiotics biosynthesized in divergent pathways with vanadium-dependent chloroperoxidases.

Authors:  Leonard Kaysser; Peter Bernhardt; Sang-Jip Nam; Sandra Loesgen; J Graham Ruby; Peter Skewes-Cox; Paul R Jensen; William Fenical; Bradley S Moore
Journal:  J Am Chem Soc       Date:  2012-07-12       Impact factor: 15.419

6.  Biomimetic synthesis of antimalarial naphthoquinones.

Authors:  Jeremiah P Malerich; Thomas J Maimone; Gregory I Elliott; Dirk Trauner
Journal:  J Am Chem Soc       Date:  2005-05-04       Impact factor: 15.419

7.  Biosynthetically Guided Structure-Activity Relationship Studies of Merochlorin A, an Antibiotic Marine Natural Product.

Authors:  Borja López-Pérez; Henry P Pepper; Rong Ma; Benjamin J Fawcett; Ashok D Pehere; Qi Wei; Zengchun Ji; Steven W Polyak; Huanqin Dai; Fuhang Song; Andrew D Abell; Lixin Zhang; Jonathan H George
Journal:  ChemMedChem       Date:  2017-11-23       Impact factor: 3.466

8.  Characterization and Biochemical Assays of Streptomyces Vanadium-Dependent Chloroperoxidases.

Authors:  Shaun M K McKinnie; Zachary D Miles; Bradley S Moore
Journal:  Methods Enzymol       Date:  2018-04-02       Impact factor: 1.600

9.  Enantioselective total synthesis of (-)-napyradiomycin A1 via asymmetric chlorination of an isolated olefin.

Authors:  Scott A Snyder; Zhen-Yu Tang; Ritu Gupta
Journal:  J Am Chem Soc       Date:  2009-04-29       Impact factor: 15.419

Review 10.  Biosynthetic studies on terpenoids produced by Streptomyces.

Authors:  Tomohisa Kuzuyama
Journal:  J Antibiot (Tokyo)       Date:  2017-02-15       Impact factor: 2.649
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  10 in total

1.  Meroterpenoid natural products from Streptomyces bacteria - the evolution of chemoenzymatic syntheses.

Authors:  Lauren A M Murray; Shaun M K McKinnie; Bradley S Moore; Jonathan H George
Journal:  Nat Prod Rep       Date:  2020-06-30       Impact factor: 13.423

2.  Total Synthesis of (+)-Granatumine A and Related Bislactone Limonoid Alkaloids via a Pyran to Pyridine Interconversion.

Authors:  Alexander W Schuppe; Yizhou Zhao; Yannan Liu; Timothy R Newhouse
Journal:  J Am Chem Soc       Date:  2019-06-03       Impact factor: 15.419

3.  Total Enzyme Syntheses of Napyradiomycins A1 and B1.

Authors:  Shaun M K McKinnie; Zachary D Miles; Peter A Jordan; Takayoshi Awakawa; Henry P Pepper; Lauren A M Murray; Jonathan H George; Bradley S Moore
Journal:  J Am Chem Soc       Date:  2018-12-14       Impact factor: 15.419

4.  Synthesis of (±)-Setigerumine I: Biosynthetic Origins of the Elusive Racemic Papaveraceae Isoxazolidine Alkaloids*.

Authors:  Ana V Serna; László Kürti; Juha H Siitonen
Journal:  Angew Chem Int Ed Engl       Date:  2021-11-18       Impact factor: 15.336

Review 5.  Cryptic halogenation reactions in natural product biosynthesis.

Authors:  Sanjoy Adak; Bradley S Moore
Journal:  Nat Prod Rep       Date:  2021-10-20       Impact factor: 15.111

Review 6.  Terpene synthases in disguise: enzymology, structure, and opportunities of non-canonical terpene synthases.

Authors:  Jeffrey D Rudolf; Chin-Yuan Chang
Journal:  Nat Prod Rep       Date:  2020-03-25       Impact factor: 13.423

Review 7.  Bacterial terpenome.

Authors:  Jeffrey D Rudolf; Tyler A Alsup; Baofu Xu; Zining Li
Journal:  Nat Prod Rep       Date:  2021-05-26       Impact factor: 15.111

8.  Biosynthesis of Largimycins in Streptomyces argillaceus Involves Transient β-Alkylation and Cryptic Halogenation Steps Unprecedented in the Leinamycin Family.

Authors:  Adriana Becerril; Ignacio Pérez-Victoria; Jesús M Martín; Fernando Reyes; Jose A Salas; Carmen Méndez
Journal:  ACS Chem Biol       Date:  2022-07-13       Impact factor: 4.634

9.  Acceptor substrate determines donor specificity of an aromatic prenyltransferase: expanding the biocatalytic potential of NphB.

Authors:  Bryce P Johnson; Erin M Scull; Dustin A Dimas; Tejaswi Bavineni; Chandrasekhar Bandari; Andrea L Batchev; Eric D Gardner; Susan L Nimmo; Shanteri Singh
Journal:  Appl Microbiol Biotechnol       Date:  2020-03-18       Impact factor: 4.813

10.  Investigating the Role of Vanadium-Dependent Haloperoxidase Enzymology in Microbial Secondary Metabolism and Chemical Ecology.

Authors:  Jackson T Baumgartner; Shaun M K McKinnie
Journal:  mSystems       Date:  2021-08-24       Impact factor: 6.496
  10 in total

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