Literature DB >> 17017767

Pentalenolactone biosynthesis. Molecular cloning and assignment of biochemical function to PtlI, a cytochrome P450 of Streptomyces avermitilis.

Richard Quaderer1, Satoshi Omura, Haruo Ikeda, David E Cane.   

Abstract

A gene cluster encoding all of the enzymes for the biosynthesis of the antibiotic pentalenolactone (1) has recently been identified in Streptomyces avermitilis. The biosynthetic gene cluster contains the ptlI (SAV2999) gene which encodes a cytochrome P450 (CYP183A1). PtlI was cloned by PCR and expressed in Escherichia coli as a C-terminal His6-tag protein. Recombinant PtlI bound pentalenene (3) with high affinity (KD = 1.44 +/- 0.14 muM). Incubation of recombinant PtlI with (+/-)-3 in the presence of NADPH, E. coli flavodoxin and flavodoxin reductase, and O2 resulted in conversion to a single enantiomer of pentalen-13-al (7), by stepwise allylic oxidation via pentalen-13-ol (6). The steady-state kinetic parameters for the oxidation of pentalenene (3) to pentalen-13-ol (6) were kcat = 0.503 +/- 0.006 min-1 and Km = 3.33+/-0.62 muM for 3.

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Year:  2006        PMID： 17017767      PMCID： PMC2533730          DOI： 10.1021/ja0639214

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


  20 in total

1.  Heme-Containing Oxygenases.

Authors:  Masanori Sono; Mark P. Roach; Eric D. Coulter; John H. Dawson
Journal:  Chem Rev       Date:  1996-11-07       Impact factor: 60.622

2.  THE CARBON MONOXIDE-BINDING PIGMENT OF LIVER MICROSOMES. I. EVIDENCE FOR ITS HEMOPROTEIN NATURE.

Authors:  T OMURA; R SATO
Journal:  J Biol Chem       Date:  1964-07       Impact factor: 5.157

3.  NADPH-flavodoxin reductase and flavodoxin from Escherichia coli: characteristics as a soluble microsomal P450 reductase.

Authors:  C M Jenkins; M R Waterman
Journal:  Biochemistry       Date:  1998-04-28       Impact factor: 3.162

4.  Measurement of substrate and inhibitor binding to microsomal cytochrome P-450 by optical-difference spectroscopy.

Authors:  C R Jefcoate
Journal:  Methods Enzymol       Date:  1978       Impact factor: 1.600

5.  Artemisia annua L. (Asteraceae) trichome-specific cDNAs reveal CYP71AV1, a cytochrome P450 with a key role in the biosynthesis of the antimalarial sesquiterpene lactone artemisinin.

Authors:  Keat H Teoh; Devin R Polichuk; Darwin W Reed; Goska Nowak; Patrick S Covello
Journal:  FEBS Lett       Date:  2006-01-30       Impact factor: 4.124

6.  Pentalenolactone biosynthesis. Molecular cloning and assignment of biochemical function to PtlH, a non-heme iron dioxygenase of Streptomyces avermitilis.

Authors:  Zheng You; Satoshi Omura; Haruo Ikeda; David E Cane
Journal:  J Am Chem Soc       Date:  2006-05-24       Impact factor: 15.419

7.  Characterization of human sterol 27-hydroxylase. A mitochondrial cytochrome P-450 that catalyzes multiple oxidation reaction in bile acid biosynthesis.

Authors:  J J Cali; D W Russell
Journal:  J Biol Chem       Date:  1991-04-25       Impact factor: 5.157

8.  Flavodoxin and NADPH-flavodoxin reductase from Escherichia coli support bovine cytochrome P450c17 hydroxylase activities.

Authors:  C M Jenkins; M R Waterman
Journal:  J Biol Chem       Date:  1994-11-04       Impact factor: 5.157

9.  Arabidopsis ent-kaurene oxidase catalyzes three steps of gibberellin biosynthesis.

Authors:  C A Helliwell; A Poole; W J Peacock; E S Dennis
Journal:  Plant Physiol       Date:  1999-02       Impact factor: 8.340

10.  Studies on biosynthesis of pentalenolactone. V isolation of deoxypentalenylglucuron.

Authors:  S Takahashi; M Takeuchi; M Arai; H Seto; N Otake
Journal:  J Antibiot (Tokyo)       Date:  1983-03       Impact factor: 2.649
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  22 in total

Review 1.  Genome mining of the Streptomyces avermitilis genome and development of genome-minimized hosts for heterologous expression of biosynthetic gene clusters.

Authors:  Haruo Ikeda; Shin-ya Kazuo; Satoshi Omura
Journal:  J Ind Microbiol Biotechnol       Date:  2013-08-29       Impact factor: 3.346

2.  Genome mining in streptomyces. Discovery of an unprecedented P450-catalyzed oxidative rearrangement that is the final step in the biosynthesis of pentalenolactone.

Authors:  Dongqing Zhu; Myung-Ji Seo; Haruo Ikeda; David E Cane
Journal:  J Am Chem Soc       Date:  2011-02-01       Impact factor: 15.419

3.  Pentalenolactone biosynthesis: Molecular cloning and assignment of biochemical function to PtlF, a short-chain dehydrogenase from Streptomyces avermitilis, and identification of a new biosynthetic intermediate.

Authors:  Zheng You; Satoshi Omura; Haruo Ikeda; David E Cane
Journal:  Arch Biochem Biophys       Date:  2006-11-22       Impact factor: 4.013

4.  FK506 maturation involves a cytochrome p450 protein-catalyzed four-electron C-9 oxidation in parallel with a C-31 O-methylation.

Authors:  Dandan Chen; Lihan Zhang; Bo Pang; Jing Chen; Zhinan Xu; Ikuro Abe; Wen Liu
Journal:  J Bacteriol       Date:  2013-02-22       Impact factor: 3.490

Review 5.  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

6.  Identification of functional cytochrome P450 and ferredoxin from Streptomyces sp. EAS-AB2608 by transcriptional analysis and their heterologous expression.

Authors:  Shinya Okubo; Eri Ena; Akifumi Okuda; Ikuko Kozone; Junko Hashimoto; Yoshie Nishitsuji; Manabu Fujie; Noriyuki Satoh; Haruo Ikeda; Kazuo Shin-Ya
Journal:  Appl Microbiol Biotechnol       Date:  2021-05-04       Impact factor: 4.813

Review 7.  Cytochromes P450 for natural product biosynthesis in Streptomyces: sequence, structure, and function.

Authors:  Jeffrey D Rudolf; Chin-Yuan Chang; Ming Ma; Ben Shen
Journal:  Nat Prod Rep       Date:  2017-08-30       Impact factor: 13.423

Review 8.  Exploration and mining of the bacterial terpenome.

Authors:  David E Cane; Haruo Ikeda
Journal:  Acc Chem Res       Date:  2011-10-31       Impact factor: 22.384

9.  Product-mediated regulation of pentalenolactone biosynthesis in Streptomyces species by the MarR/SlyA family activators PenR and PntR.

Authors:  Dongqing Zhu; Yinping Wang; Manman Zhang; Haruo Ikeda; Zixin Deng; David E Cane
Journal:  J Bacteriol       Date:  2013-01-11       Impact factor: 3.490

10.  Pyran formation by an atypical CYP-mediated four-electron oxygenation-cyclization cascade in an engineered aureothin pathway.

Authors:  Martin Richter; Benjamin Busch; Keishi Ishida; Bradley S Moore; Christian Hertweck
Journal:  Chembiochem       Date:  2012-09-07       Impact factor: 3.164
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