Literature DB >> 23274670

Function of cytochrome P450 enzymes RosC and RosD in the biosynthesis of rosamicin macrolide antibiotic produced by Micromonospora rosaria.

Yohei Iizaka1, Noriko Higashi, Masanari Ishida, Reina Oiwa, Yumi Ichikawa, Moeka Takeda, Yojiro Anzai, Fumio Kato.   

Abstract

The cytochrome P450 enzyme-encoding genes rosC and rosD were cloned from the rosamicin biosynthetic gene cluster of Micromonospora rosaria IFO13697. The functions of RosC and RosD were demonstrated by gene disruption and complementation with M. rosaria and bioconversion of rosamicin biosynthetic intermediates with Escherichia coli expressing RosC and RosD. It is proposed that M. rosaria IFO13697 has two pathway branches that lead from the first desosaminyl rosamicin intermediate, 20-deoxo-20-dihydro-12,13-deepoxyrosamicin, to rosamicin.

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Year:  2012        PMID: 23274670      PMCID: PMC3591866          DOI: 10.1128/AAC.02092-12

Source DB:  PubMed          Journal:  Antimicrob Agents Chemother        ISSN: 0066-4804            Impact factor:   5.191


  15 in total

1.  Isolation and characterization of 23-O-mycinosyl-20-dihydro-rosamicin: a new rosamicin analogue derived from engineered Micromonospora rosaria.

Authors:  Yojiro Anzai; Ayami Sakai; Wei Li; Yohei Iizaka; Kazuo Koike; Kenji Kinoshita; Fumio Kato
Journal:  J Antibiot (Tokyo)       Date:  2010-04-23       Impact factor: 2.649

2.  Hydroxylation of testosterone by bacterial cytochromes P450 using the Escherichia coli expression system.

Authors:  Hitosi Agematu; Naoki Matsumoto; Yoshikazu Fujii; Hiroki Kabumoto; Satoru Doi; Kazuhiro Machida; Jun Ishikawa; Akira Arisawa
Journal:  Biosci Biotechnol Biochem       Date:  2006-01       Impact factor: 2.043

3.  Macrolide antibiotics M-4365 produced by Micromonospora. II. Chemical structures.

Authors:  A Kinumaki; K I Harada; T Suzuki; M Suzuki; T Okuda
Journal:  J Antibiot (Tokyo)       Date:  1977-06       Impact factor: 2.649

4.  A cytochrome P450-like gene possibly involved in oleandomycin biosynthesis by Streptomyces antibioticus.

Authors:  A M Rodriguez; C Olano; C Méndez; C R Hutchinson; J A Salas
Journal:  FEMS Microbiol Lett       Date:  1995-03-15       Impact factor: 2.742

5.  Gene targeting for O-methyltransferase genes, mycE and mycF, on the chromosome of Micromonospora griseorubida producing mycinamicin with a disruption cassette containing the bacteriophage phi C31 attB attachment site.

Authors:  Shu-ichi Tsukada; Yojiro Anzai; Shengying Li; Kenji Kinoshita; David H Sherman; Fumio Kato
Journal:  FEMS Microbiol Lett       Date:  2010-01-11       Impact factor: 2.742

6.  Production of hybrid 16-membered macrolides by expressing combinations of polyketide synthase genes in engineered Streptomyces fradiae hosts.

Authors:  Christopher D Reeves; Shannon L Ward; W Peter Revill; Hideki Suzuki; Matthew Marcus; Oleg V Petrakovsky; Saul Marquez; Hong Fu; Steven D Dong; Leonard Katz
Journal:  Chem Biol       Date:  2004-10

7.  Production of rosamicin derivatives in Micromonospora rosaria by introduction of D-mycinose biosynthetic gene with PhiC31-derived integration vector pSET152.

Authors:  Yojiro Anzai; Yohei Iizaka; Wei Li; Naoki Idemoto; Shu-ichi Tsukada; Kazuo Koike; Kenji Kinoshita; Fumio Kato
Journal:  J Ind Microbiol Biotechnol       Date:  2009-05-02       Impact factor: 3.346

8.  PCR-targeted Streptomyces gene replacement identifies a protein domain needed for biosynthesis of the sesquiterpene soil odor geosmin.

Authors:  Bertolt Gust; Greg L Challis; Kay Fowler; Tobias Kieser; Keith F Chater
Journal:  Proc Natl Acad Sci U S A       Date:  2003-01-31       Impact factor: 11.205

9.  Organization of the biosynthetic gene cluster for the macrolide antibiotic spiramycin in Streptomyces ambofaciens.

Authors:  Fatma Karray; Emmanuelle Darbon; Nathalie Oestreicher; Hélène Dominguez; Karine Tuphile; Josette Gagnat; Marie-Hélène Blondelet-Rouault; Claude Gerbaud; Jean-Luc Pernodet
Journal:  Microbiology       Date:  2007-12       Impact factor: 2.777

10.  Engineered biosynthesis of hybrid macrolide polyketides containing D-angolosamine and D-mycaminose moieties.

Authors:  Ursula Schell; Stephen F Haydock; Andrew L Kaja; Isabelle Carletti; Rachel E Lill; Eliot Read; Lesley S Sheehan; Lindsey Low; Maria-Jose Fernandez; Friederike Grolle; Hamish A I McArthur; Rose M Sheridan; Peter F Leadlay; Barrie Wilkinson; Sabine Gaisser
Journal:  Org Biomol Chem       Date:  2008-07-28       Impact factor: 3.876

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  8 in total

1.  Salinipyrone and Pacificanone Are Biosynthetic By-products of the Rosamicin Polyketide Synthase.

Authors:  Takayoshi Awakawa; Max Crüsemann; Jason Munguia; Nadine Ziemert; Victor Nizet; William Fenical; Bradley S Moore
Journal:  Chembiochem       Date:  2015-05-15       Impact factor: 3.164

Review 2.  An overview of the cytochrome P450 enzymes that catalyze the same-site multistep oxidation reactions in biotechnologically relevant selected actinomycete strains.

Authors:  Yohei Iizaka; David H Sherman; Yojiro Anzai
Journal:  Appl Microbiol Biotechnol       Date:  2021-03-12       Impact factor: 4.813

3.  Targeting Reactive Carbonyls for Identifying Natural Products and Their Biosynthetic Origins.

Authors:  Tucker Maxson; Jonathan I Tietz; Graham A Hudson; Xiao Rui Guo; Hua-Chia Tai; Douglas A Mitchell
Journal:  J Am Chem Soc       Date:  2016-11-14       Impact factor: 15.419

4.  A new mycinosyl rosamicin derivative produced by an engineered Micromonospora rosaria mutant with a cytochrome P450 gene disruption introducing the D-mycinose biosynthetic gene.

Authors:  Yohei Iizaka; Noriko Higashi; Wei Li; Atsushi Fukumoto; Yojiro Anzai; Fumio Kato
Journal:  J Ind Microbiol Biotechnol       Date:  2014-07-22       Impact factor: 3.346

5.  Chemoenzymatic Total Synthesis and Structural Diversification of Tylactone-Based Macrolide Antibiotics through Late-Stage Polyketide Assembly, Tailoring, and C-H Functionalization.

Authors:  Andrew N Lowell; Matthew D DeMars; Samuel T Slocum; Fengan Yu; Krithika Anand; Joseph A Chemler; Nisha Korakavi; Jennifer K Priessnitz; Sung Ryeol Park; Aaron A Koch; Pamela J Schultz; David H Sherman
Journal:  J Am Chem Soc       Date:  2017-06-05       Impact factor: 15.419

Review 6.  Natural products from thioester reductase containing biosynthetic pathways.

Authors:  Michael W Mullowney; Ryan A McClure; Matthew T Robey; Neil L Kelleher; Regan J Thomson
Journal:  Nat Prod Rep       Date:  2018-09-19       Impact factor: 13.423

7.  Post-PKS tailoring steps of the spiramycin macrolactone ring in Streptomyces ambofaciens.

Authors:  Hoang-Chuong Nguyen; Emmanuelle Darbon; Robert Thai; Jean-Luc Pernodet; Sylvie Lautru
Journal:  Antimicrob Agents Chemother       Date:  2013-05-28       Impact factor: 5.191

Review 8.  P450 Monooxygenases Enable Rapid Late-Stage Diversification of Natural Products via C-H Bond Activation.

Authors:  Nico D Fessner
Journal:  ChemCatChem       Date:  2019-02-15       Impact factor: 5.686

  8 in total

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