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Design and synthesis of a beta-amino phosphotyrosyl mimetic suitably protected for peptide synthesis

  1. Author:
    Lee, K.
    Zhang, M. C.
    Yang, D. J.
    Burke, T. R.
  2. Author Address

    NCI, Med Chem Lab, Canc Res Ctr, NIH, Frederick, MD 21702 USA NCI, Med Chem Lab, Canc Res Ctr, NIH, Frederick, MD 21702 USA Univ Michigan, Dept Hematol Oncol, Ann Arbor, MI 48109 USA Burke TR NCI, Med Chem Lab, Canc Res Ctr, NIH, Frederick, MD 21702 USA
    1. Year: 2002
  1. Journal: Bioorganic & Medicinal Chemistry Letters
    1. 12
    2. 23
    3. Pages: 3399-3401
  2. Type of Article: Article
  1. Abstract:

    Mimetics of phosphotyrosine (pTyr) such as phosphonomethylphertylalanine (Pmp) have traditionally retained a-amino functionality. However, beta-amino acids represent isomeric variants, which may exhibit properties that are distinct from the parent. Reported herein is the first beta- amino pTyr mimetic (Pmp(beta)) bearing protection suitable for peptide synthesis. Preparation of Pmp(beta) was accomplished enantioselectively in 43% overall yield from commercially available 4-vinylbenzyl chloride. (C) 2002 Elsevier Science Ltd. All rights reserved.

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