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Enantioselective synthesis of N-alpha-Fmoc protected (2S,3R)-3- phenylpipecolic acid. A constrained phenylalanine analogue suitably protected for solid-phase peptide synthesis

  1. Author:
    Liu, D. G.
    Gao, Y.
    Wang, X. Z.
    Kelley, J. A.
    Burke, T. R.

  2. Author Address

    NCI, Med Chem Lab, Canc Res Ctr, NIH, Bldg 376,Boyles St,POB B, Frederick, MD 21702 USA NCI, Med Chem Lab, Canc Res Ctr, NIH, Frederick, MD 21702 USA Burke TR NCI, Med Chem Lab, Canc Res Ctr, NIH, Bldg 376,Boyles St,POB B, Frederick, MD 21702 USA
    1. Year: 2002
  2. Journal: Journal of Organic Chemistry
    1. 67
    2. 5
    3. Pages: 1448-1452
  4. Type of Article: Article
  1. Abstract:

    Reported herein is the first enantioselective preparation of (2S,3R)-3-phenylpipecolic acid as a conformationally constrained phenylalanine analogue bearing N-a-protection suitable for solid-phase peptide synthesis. Stereochemistries at both the 2- and 3-positions are derived inductively from a single chiral center provided by the commercially available Evans chiral auxiliary, (4S)-4-benzyl-1,3-oxazolidin-2-one. By constraining phi and x(1) torsion angles, this novel amino acid analogue can serve as a useful tool for the induction of defined geometry in phenylalanine-containing peptides.

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