Inactivation of the carbamoyltransferase gene refines post-polyketide synthase modification steps in the biosynthesis of the antitumor agent geldanamycin

Young Soo Hong, Dongho Lee, Woncheol Kim, Jae Kap Jeong, Chun Gyu Kim, Jae Kyung Sohng, Jeong Hyung Lee, Sang Gi Paik, Jung Joon Lee

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The post-polyketide synthase modification of geldanamycin (1) biosynthesis is of interest as a means of introducing structural diversity into the compound. From the inactivation of a gene encoding carbamoyltransferase, we demonstrated that the C-17 hydroxylation and the C-21 oxidation precede O-carbamoylation and that the hypothetical progeldanamycin does not possess a double bond at C-4 and C-5. More importantly, our result revealed new intermediates 4,5-dihydro-7-O-descarbamoyl-7-hydroxygeldanamycin (3) and 4,5-dihydrogeldanamycin (5), indicating that O-carbamoylation occurs prior to the C-4,5 cis double bond formation in geldanamycin biosynthesis.

Original languageEnglish
Pages (from-to)11142-11143
Number of pages2
JournalJournal of the American Chemical Society
Issue number36
Publication statusPublished - 2004 Sep 15
Externally publishedYes


ASJC Scopus subject areas

  • Chemistry(all)

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