Literature DB >> 24677572

Identification and characterization of a welwitindolinone alkaloid biosynthetic gene cluster in the stigonematalean Cyanobacterium Hapalosiphon welwitschii.

Matthew L Hillwig, Heather A Fuhrman, Kuljira Ittiamornkul, Tyler J Sevco, Daniel H Kwak, Xinyu Liu.   

Abstract

The identification of a 36 kb welwitindolinone (n class="Chemical">wel) biosynthetic gene cluster in Hapalosiphon welwitschii UTEX B1830 is reported. Characterization of the enzymes responsible for assembling the early biosynthetic intermediates geranyl pyrophosphate and 3-((Z)-2′-isocyanoethenyl)indole as well as a dedicated N-methyltransferase in the maturation of N-methylwelwitindolinone C isothiocyanate solidified the link between the wel pathway and welwitindolinone biosynthesis. Comparative analysis of the ambiguine and welwitindolinone biosynthetic pathways in two different organisms provided insights into the origins of diverse structures within hapalindole-type molecules.

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Year:  2014        PMID: 24677572      PMCID: PMC4382313          DOI: 10.1002/cbic.201300794

Source DB:  PubMed          Journal:  Chembiochem        ISSN: 1439-4227            Impact factor:   3.164


  24 in total

1.  Total synthesis of (-)-N-methylwelwitindolinone C isothiocyanate.

Authors:  Alexander D Huters; Kyle W Quasdorf; Evan D Styduhar; Neil K Garg
Journal:  J Am Chem Soc       Date:  2011-08-11       Impact factor: 15.419

2.  Enantiospecific total synthesis of N-methylwelwitindolinone D isonitrile.

Authors:  Evan D Styduhar; Alexander D Huters; Nicholas A Weires; Neil K Garg
Journal:  Angew Chem Int Ed Engl       Date:  2013-10-02       Impact factor: 15.336

3.  Total synthesis of N-methylwelwitindolinone D isonitrile.

Authors:  Vikram Bhat; Kevin M Allan; Viresh H Rawal
Journal:  J Am Chem Soc       Date:  2011-03-29       Impact factor: 15.419

4.  Total synthesis of (+/-)-welwitindolinone a isonitrile.

Authors:  Sarah E Reisman; Joseph M Ready; Atsushi Hasuoka; Catherine J Smith; John L Wood
Journal:  J Am Chem Soc       Date:  2006-02-08       Impact factor: 15.419

5.  A tRNA-dependent two-enzyme pathway for the generation of singly and doubly methylated ditryptophan 2,5-diketopiperazines.

Authors:  Tobias W Giessen; Alexander M von Tesmar; Mohamed A Marahiel
Journal:  Biochemistry       Date:  2013-06-07       Impact factor: 3.162

Review 6.  Trafficking in persulfides: delivering sulfur in biosynthetic pathways.

Authors:  Eugene G Mueller
Journal:  Nat Chem Biol       Date:  2006-04       Impact factor: 15.040

7.  A cytochrome P450 serves as an unexpected terpene cyclase during fungal meroterpenoid biosynthesis.

Authors:  Yit-Heng Chooi; Young J Hong; Ralph A Cacho; Dean J Tantillo; Yi Tang
Journal:  J Am Chem Soc       Date:  2013-11-01       Impact factor: 15.419

8.  Microtubule effects of welwistatin, a cyanobacterial indolinone that circumvents multiple drug resistance.

Authors:  X Zhang; C D Smith
Journal:  Mol Pharmacol       Date:  1996-02       Impact factor: 4.436

9.  Biosynthesis of ambiguine indole alkaloids in cyanobacterium Fischerella ambigua.

Authors:  Matthew L Hillwig; Qin Zhu; Xinyu Liu
Journal:  ACS Chem Biol       Date:  2013-11-20       Impact factor: 5.100

10.  Cannabidiolic-acid synthase, the chemotype-determining enzyme in the fiber-type Cannabis sativa.

Authors:  Futoshi Taura; Supaart Sirikantaramas; Yoshinari Shoyama; Kazuyoshi Yoshikai; Yukihiro Shoyama; Satoshi Morimoto
Journal:  FEBS Lett       Date:  2007-05-25       Impact factor: 4.124

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  24 in total

1.  Enzymology: A radical finding.

Authors:  Rebecca J M Goss; Sabine Grüschow
Journal:  Nat Chem Biol       Date:  2014-09-14       Impact factor: 15.040

2.  Hapalindole/Ambiguine Biogenesis Is Mediated by a Cope Rearrangement, C-C Bond-Forming Cascade.

Authors:  Shasha Li; Andrew N Lowell; Fengan Yu; Avi Raveh; Sean A Newmister; Nathan Bair; Jeffrey M Schaub; Robert M Williams; David H Sherman
Journal:  J Am Chem Soc       Date:  2015-12-02       Impact factor: 15.419

Review 3.  Enzymatic Halogenation and Dehalogenation Reactions: Pervasive and Mechanistically Diverse.

Authors:  Vinayak Agarwal; Zachary D Miles; Jaclyn M Winter; Alessandra S Eustáquio; Abrahim A El Gamal; Bradley S Moore
Journal:  Chem Rev       Date:  2017-01-20       Impact factor: 60.622

4.  Control of Stereoselectivity in Diverse Hapalindole Metabolites is Mediated by Cofactor-Induced Combinatorial Pairing of Stig Cyclases.

Authors:  Shasha Li; Sean A Newmister; Andrew N Lowell; Jiachen Zi; Callie R Chappell; Fengan Yu; Robert M Hohlman; Jimmy Orjala; Robert M Williams; David H Sherman
Journal:  Angew Chem Int Ed Engl       Date:  2020-03-19       Impact factor: 15.336

Review 5.  Comparison of Strategies to Overcome Drug Resistance: Learning from Various Kingdoms.

Authors:  Hiroshi Ogawara
Journal:  Molecules       Date:  2018-06-18       Impact factor: 4.411

6.  Scalable Total Syntheses of (-)-Hapalindole U and (+)-Ambiguine H.

Authors:  Thomas J Maimone; Yoshihiro Ishihara; Phil S Baran
Journal:  Tetrahedron       Date:  2015-05-02       Impact factor: 2.457

7.  Structure-Guided Reprogramming of a Hydroxylase To Halogenate Its Small Molecule Substrate.

Authors:  Andrew J Mitchell; Noah P Dunham; Jonathan A Bergman; Bo Wang; Qin Zhu; Wei-Chen Chang; Xinyu Liu; Amie K Boal
Journal:  Biochemistry       Date:  2017-01-11       Impact factor: 3.162

8.  Unified biogenesis of ambiguine, fischerindole, hapalindole and welwitindolinone: identification of a monogeranylated indolenine as a cryptic common biosynthetic intermediate by an unusual magnesium-dependent aromatic prenyltransferase.

Authors:  Xinyu Liu; Matthew L Hillwig; Leonardus M I Koharudin; Angela M Gronenborn
Journal:  Chem Commun (Camb)       Date:  2016-01-07       Impact factor: 6.222

9.  A new family of iron-dependent halogenases acts on freestanding substrates.

Authors:  Matthew L Hillwig; Xinyu Liu
Journal:  Nat Chem Biol       Date:  2014-09-14       Impact factor: 15.040

Review 10.  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

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