Biosynthesis of lactacystin.

نویسندگان

  • S Takahashi
  • K Uchida
  • A Nakagawa
  • Y Miyake
  • M Kainosho
  • K Matsuzaki
  • S Omura
چکیده

The biosynthesis of lactacystin, a new microbial metabolite which induces differentiation of neuroblastoma cells, was studied by the feeding experiments of various 13C-labeled compounds and NMR spectroscopic analysis. The feeding experiments showed that lactacystin consists of three containing gamma-lactam moiety arises by a condensation between methylmalonic semialdehyde and C alpha position of L-leucine, followed by intramolecular cyclization. Two diastereotopic methyls, C-11 and C-12 of lactacystin were found to originate from the pro-R and pro-S methyls of leucine, respectively, as shown by incorporating a new type of chiral 13C-labeled L-leucine.

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عنوان ژورنال:
  • The Journal of antibiotics

دوره 48 9  شماره 

صفحات  -

تاریخ انتشار 1995