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

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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

ASJC Scopus subject areas

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

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    Lee, S. K., Park, J. W., Kim, J. W., Jung, W. S., Park, S. R., Choi, C. Y., Kim, E. S., Kim, B. S., Ahn, J. S., Sherman, D. H., & Yoon, Y. J. (2006). Neopikromycin and novapikromycin from the pikromycin biosynthetic pathway of Streptomyces venezuelae. Journal of Natural Products, 69(5), 847-849. https://doi.org/10.1021/np060026p