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Biosynthesis of the beta-amino acid moiety of the enediyne antitumor antibiotic c-1027 featuring beta-amino acyl-s-carrier protein intermediates

Academic Article
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Overview

authors

  • Van Lanen, S. G.
  • Dorrestein, P. C.
  • Christenson, S. D.
  • Liu, W.
  • Ju, J. H.
  • Kelleher, N. L.
  • Shen, Ben

publication date

  • August 2005

journal

  • Journal of the American Chemical Society  Journal

abstract

  • The enediyne antitumor antibiotic C-1027 chromoprotein is produced by Streptomyces globisporus. The biosynthesis of the (S)-3-chloro-4,5-dihydroxy-beta-phenylalanine moiety (boxed) of the C-1027 chromophore (1) from l-tyrosine (3) and its incorporation into 1 are catalyzed by six enzymes: SgcC, SgcC1, SgcC2, SgcC3, SgcC4, ShcC5. In vivo and in vitro characterization of these enzymes delineated this pathway, unveiling a novel strategy for beta-amino acid modification featuring beta-amino acyl-S-carrier protein intermediates. These findings shed new light into beta-amino acid biosynthesis and present a new opportunity to engineer the C-1027 biosynthetic machinery for the production of novel analogues as exemplified by 20-deschloro-C-1027 (4), 20-deschro-22-deshydroxy-C-1027 (5), and 22-deshydroxy-C-1027 (6).

subject areas

  • Acyl Carrier Protein
  • Amino Acids
  • Aminoglycosides
  • Antibiotics, Antineoplastic
  • Enediynes
  • Enzymes
  • Molecular Conformation
  • Stereoisomerism
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Identity

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja052871k

PubMed ID

  • 16104723
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Additional Document Info

start page

  • 11594

end page

  • 11595

volume

  • 127

issue

  • 33

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