2. Academic Validation
  3. Synthesis and biological evaluation of tubulysin D analogs related to stereoisomers of tubuvaline

Synthesis and biological evaluation of tubulysin D analogs related to stereoisomers of tubuvaline

  • Bioorg Med Chem Lett. 2011 Jan 1;21(1):431-4. doi: 10.1016/j.bmcl.2010.10.118.
Taku Shibue 1,  Iwao Okamoto,  Nobuyoshi Morita,  Hiroshi Morita,  Yusuke Hirasawa,  Takahiro Hosoya,  Osamu Tamura
Affiliations

Affiliation

  • 1 Exploratory Research Laboratories, Kyorin Pharmaceutical Co Ltd, 2399-1 Nogi, Nogi-Machi, Shimotsuga-Gun, Tochigi 329-0114, Japan.
PMID: 21106374 DOI: 10.1016/j.bmcl.2010.10.118
Abstract

The synthesis and biological evaluation of stereoisomers in tubulysin D are described. The stereoselective synthesis of all possible stereoisomers of C-11 and C-13 positions in tubulysin D was achieved by employing 1'-epi-Tuv-Me, 3'-epi-Tuv-Me, and ent-Tuv-Me and their biological properties were evaluated. It is clear that the stereochemistries of the C-11 and C-13 positions in tubulysin D have no practical impact on the inhibition of tubulin polymerization but play a role in the potent antiproliferative activities.

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