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Synlett 2000; 2000(1): 134-136
DOI: 10.1055/s-2000-6464
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Stereoselective Preparation of l-4-(2′-Malonyl)phenylalanine Suitably Protected for Fmoc-Based Synthesis of Potent Signal Transduction Inhibitory Ligands

Yang Gao* , Terrence R. Burke, Jr.
  • *Laboratory of Medicinal Chemistry, Division of Basic Sciences, National Cancer Institute, National Institutes of Health, Blg. 37, Rm. 5C06, Bethesda, MD 20817, U.S.A.; Fax + 1-301-402-2275; E-mail: tburke@helix.nih.gov
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Publication Date:
31 December 2000 (online)

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Preparation is reported of N-Fmoc 4-(2′-(di-tert-butylmalonyl))-l-phenylalanine, a useful reagent for the synthesis of signal transduction-directed ligands containing p-(2′-malonyl)phenylalanine (pmF), one of the most potent pTyr mimetics yet described for the inhibition of Grb2 SH2 domain binding. An important aspect of the current synthetic approach, is the introduction of chirality using the Williams auxiliary, benzyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate.

phosphotyrosine mimetic - stereoselective - amino acid analogue - SH2 domain