Neopikromycin and novapikromycin from the pikromycin biosynthetic pathway of Streptomyces venezuelae

Sang Kil Lee, Je Won Park, Ji Won Kim, Won Seok Jung, Sung Ryeol Park, Cha Yong Choi, Eung Soo Kim, Beom Seok Kim, Jong Seog Ahn, David H. Sherman, Yeo Joon Yoon

Research output: Contribution to journalArticle

41 Citations (Scopus)

Abstract

Two new macrolides from the pikromycin biosynthetic pathway of Streptomyces venezuelae, neopikromycin (9) and novapikromycin (10), were identified and structurally characterized through mass spectrometry and NMR spectroscopy. The established structures showed that 9 and 10 have hydroxyl groups at C-14 (9) and at both C-12 and C-14 (10), on the basis of a comparison with narbomycin (7). The purified PikC cytochrome P450 monooxygenase catalyzes the in vitro hydroxylation of 7 and pikromycin (8) to yield 9 and 10, respectively, thus expanding the substrate- and regio-flexibility of this enzyme.

Original languageEnglish
Pages (from-to)847-849
Number of pages3
JournalJournal of Natural Products
Volume69
Issue number5
DOIs
Publication statusPublished - 2006 May 1

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Streptomyces venezuelae
macrolides
Biosynthetic Pathways
Streptomyces
hydroxylation
cytochrome P-450
biochemical pathways
nuclear magnetic resonance spectroscopy
Mass Spectrometry
mass spectrometry
Hydroxylation
Macrolides
enzymes
Mixed Function Oxygenases
Hydroxyl Radical
Cytochrome P-450 Enzyme System
Nuclear magnetic resonance spectroscopy
Mass spectrometry
Magnetic Resonance Spectroscopy
Substrates

ASJC Scopus subject areas

  • Plant Science
  • Chemistry (miscellaneous)
  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

Cite this

Neopikromycin and novapikromycin from the pikromycin biosynthetic pathway of Streptomyces venezuelae. / Lee, Sang Kil; Park, Je Won; Kim, Ji Won; Jung, Won Seok; Park, Sung Ryeol; Choi, Cha Yong; Kim, Eung Soo; Kim, Beom Seok; Ahn, Jong Seog; Sherman, David H.; Yoon, Yeo Joon.

In: Journal of Natural Products, Vol. 69, No. 5, 01.05.2006, p. 847-849.

Research output: Contribution to journalArticle

Lee, SK, Park, JW, Kim, JW, Jung, WS, Park, SR, Choi, CY, Kim, ES, Kim, BS, Ahn, JS, Sherman, DH & Yoon, YJ 2006, 'Neopikromycin and novapikromycin from the pikromycin biosynthetic pathway of Streptomyces venezuelae', Journal of Natural Products, vol. 69, no. 5, pp. 847-849. https://doi.org/10.1021/np060026p
Lee, Sang Kil ; Park, Je Won ; Kim, Ji Won ; Jung, Won Seok ; Park, Sung Ryeol ; Choi, Cha Yong ; Kim, Eung Soo ; Kim, Beom Seok ; Ahn, Jong Seog ; Sherman, David H. ; Yoon, Yeo Joon. / Neopikromycin and novapikromycin from the pikromycin biosynthetic pathway of Streptomyces venezuelae. In: Journal of Natural Products. 2006 ; Vol. 69, No. 5. pp. 847-849.
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