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Concise and enantioselective synthesis of Fmoc-Pmp(BUt)(2)-OH and design of potent Pmp-containing Grb2-SH2 domain antagonists

  1. Author:
    Li, P.
    Zhang, M. C.
    Peach, M. L.
    Liu, H. P.
    Yang, D. J.
    Roller, P. P.

  2. Author Address

    NCI, Med Chem Lab, NIH, Ft Detrick, MD 21702 USA NCI, Med Chem Lab, NIH, Ft Detrick, MD 21702 USA Univ Michigan, Sch Med, Ann Arbor, MI 48109 USA Li P NCI, Med Chem Lab, NIH, Ft Detrick, MD 21702 USA
    1. Year: 2003
  2. Journal: Organic Letters
    1. 5
    2. 17
    3. Pages: 3095-3098
  4. Type of Article: Article
  1. Abstract:

    L-Phosphonomethylphenylalanine (L-Pmp) is an important phosphatase-resistant pTyr analogue. A most concise and stereoselective approach to the synthesis of the suitably protected Fmoc-Pmp(Bu-t)(2)-OH was developed in order to incorporate the functionally significant L-Pmp residue into peptides and peptidomimetics efficiently using standard Fmoc protocol. With this key building block, we are able to efficiently synthesize a series of potent Pmp-containing Grb2- SH2 domain antagonists, which can be used as chemotherapeutic leads for the treatment of erbB2-overexpressed breast cancer.

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