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Synthesis 1997; 1997(8): 921-924
DOI: 10.1055/s-1997-1297
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Synthesis of N-Substituted 10-Des(carbamoyloxy)-10-azidomitomycins

Nam Huh1 , Timothy P. Kogan2 , Harold Kohn3
  • 1Department of Chemistry, University of Houston, Houston, Texas 77204-5641, USA
  • 2Texas Biotechnology Corporation, 7000 Fannin, Suite 1920, Houston, Texas 77030, USA, Fax +1(713)7968232; E-mail: tkogan@tbc.com
  • 3Department of Chemistry, University of Houston, Houston, Texas 77204-5641, USA, Fax +1(713)7432709; E-mail: HKohn@uh.edu
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Publication Date:
31 December 2000 (online)

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A general method for the synthesis of N-substituted 10-des(carbamoyloxy)-10-azidomitomycins 5 has been developed. These compounds are expected to be rapidly converted to the corresponding C-10 isothiocyanate derivatives allowing mitomycins to couple to biomolecules. The key synthetic intermediate was 10-des(carbamoyloxy)-10-azidomitomycin C (12). Compound 12 was prepared by decarbamoylation of mitomycin C (1) followed by aziridine protection with Fmoc-chloride and activation of the C-10 site with methanesulfonyl chloride. Deprotection of the Fmoc unit with morpholine and treatment with NaN3 gave 12.

General synthesis of N-substituted 10-des(carbamoyloxy)-10-azido-mitomycins: useful compounds for bioconjugation