A new efficient enantioselective synthesis of malonylphenylalanyl and malonylmethylphenylalanyl derivatives suitable for solid phase peptide synthesis

We describe the enantioselective synthesis of two para-malonylphenylalanyl and para-malonylmethylphenylalanyl derivatives suitably protected by Fmoc, Boc or Cbz. These compounds can be incorporated into peptides by solid phase synthesis. A new synthesis of enantiomerically pure malonylphenylalanyl a...

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Bibliographic Details
Published in:Tetrahedron letters 2005-05, Vol.46 (19), p.3319-3322
Main Authors: Chen, Huixiong, Luzy, Jean-Philippe, Garbay, Christiane
Format: Article
Language:English
Subjects:
Enantioselective synthesis
Phosphotyrosine mimetics
SH2 domain
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Summary:We describe the enantioselective synthesis of two para-malonylphenylalanyl and para-malonylmethylphenylalanyl derivatives suitably protected by Fmoc, Boc or Cbz. These compounds can be incorporated into peptides by solid phase synthesis. A new synthesis of enantiomerically pure malonylphenylalanyl and malonylmethylphenylalanyl derivatives was developed in which the corresponding prochiral enamides were treated by asymmetric hydrogenation using the Rh(I)-( S, S)-Me-DuPHOS system. These unnatural amino acids were suitably protected and can be used in solid phase peptide synthesis.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2005.03.105