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Antineoplastic agents. 599. Total synthesis of dolastatin 16.
Pettit, George R; Smith, Thomas H; Arce, Pablo M; Flahive, Erik J; Anderson, Collin R; Chapuis, Jean-Charles; Xu, Jun-Ping; Groy, Thomas L; Belcher, Paul E; Macdonald, Christian B.
Afiliación
  • Pettit GR; Department of Chemistry and Biochemistry, Arizona State University, P.O. Box 871604, Tempe, Arizona 85287-1604, United States.
  • Smith TH; Department of Chemistry and Biochemistry, Arizona State University, P.O. Box 871604, Tempe, Arizona 85287-1604, United States.
  • Arce PM; Department of Chemistry and Biochemistry, Arizona State University, P.O. Box 871604, Tempe, Arizona 85287-1604, United States.
  • Flahive EJ; Department of Chemistry and Biochemistry, Arizona State University, P.O. Box 871604, Tempe, Arizona 85287-1604, United States.
  • Anderson CR; Department of Chemistry and Biochemistry, Arizona State University, P.O. Box 871604, Tempe, Arizona 85287-1604, United States.
  • Chapuis JC; Department of Chemistry and Biochemistry, Arizona State University, P.O. Box 871604, Tempe, Arizona 85287-1604, United States.
  • Xu JP; Department of Chemistry and Biochemistry, Arizona State University, P.O. Box 871604, Tempe, Arizona 85287-1604, United States.
  • Groy TL; Department of Chemistry and Biochemistry, Arizona State University, P.O. Box 871604, Tempe, Arizona 85287-1604, United States.
  • Belcher PE; Department of Chemistry and Biochemistry, Arizona State University, P.O. Box 871604, Tempe, Arizona 85287-1604, United States.
  • Macdonald CB; Department of Chemistry and Biochemistry, Arizona State University, P.O. Box 871604, Tempe, Arizona 85287-1604, United States.
J Nat Prod ; 78(3): 476-85, 2015 Mar 27.
Article en En | MEDLINE | ID: mdl-25689568
The first 23-step total synthesis of the cyclodepsipeptide dolastatin 16 (1) has been achieved. Synthesis of the dolaphenvaline and dolamethylleuine amino acid units using simplified methods improved the overall efficiency. The formation of the 25-membered macrocycle employing lactonization with 2-methyl-6-nitrobenzoic anhydride completed a key step in the synthesis. Regrettably, the synthetic dolastatin 16 (1), while otherwise identical (by X-ray crystal structure and spectral analyses) with the natural product, did not reproduce the powerful (nanomolar) cancer cell growth inhibition displayed by the natural isolate. Presumably this result can be attributed to conformation(s) of the synthetic dolastatin 16 (1) or to a chemically undetected component isolated with the natural product.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Depsipéptidos / Antineoplásicos Límite: Humans Idioma: En Revista: J Nat Prod Año: 2015 Tipo del documento: Article País de afiliación: Estados Unidos Pais de publicación: Estados Unidos
Texto completo
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Depsipéptidos / Antineoplásicos Límite: Humans Idioma: En Revista: J Nat Prod Año: 2015 Tipo del documento: Article País de afiliación: Estados Unidos Pais de publicación: Estados Unidos