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Synthesis of alpha,alpha-disubstituted 4-phosphonophenylalanine analogues as conformationally-constrained phosphotyrosyl mimetics

  1. Author:
    Oishi, S.
    Kang, S. U.
    Liu, H. P.
    Zhang, M. C.
    Yang, D. J.
    Deschamps, J. R.
    Burke, T. R.
  2. Author Address

    Burke, TR, NCI, Med Chem Lab, Ctr Canc Res, NIH, POB B,Bldg 376 Boyles St, Frederick, MD 21702 USA NCI, Med Chem Lab, Ctr Canc Res, NIH, Frederick, MD 21702 USA. Univ Michigan, Sch Med, Dept Hematol Oncol, Ann Arbor, MI 48109 USA. USN, Res Lab, Struct Matter Lab, Washington, DC 20375 USA.
    1. Year: 2004
  1. Journal: Tetrahedron
    1. 60
    2. 13
    3. Pages: 2971-2977
  2. Type of Article: Article
  1. Abstract:

    Syntheses of N-Boc (S)-4-(diethylphosphono)-(alpha-methyl)phenylalanine [Boc-(alpha-Me)Phe(4-PO3Et2)-OH] (9) and N-Boc (S)-2amino-6-(diethylphosphono)tetralin-2-carboxylic acid [Boc-Atc(6-PO3Et2)-OH] (18) are reported as conformationally-constrained phosphotyrosyl mimetics suitably protected for peptide synthesis. Both syntheses proceeded through chiral arylhalides that are converted to arylphosphonates by palladium-catalyzed cross coupling with diethylphosphite. These amino acid analogues may be useful in the study of cellular signal transduction processes. (C) 2004 Elsevier Ltd. All rights reserved

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