Enantioselective synthesis of stimulus-responsive amino acid via asymmetric α-amination of aldehyde

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Abstract

Development of a methodology to control the function of peptides and proteins is an indispensable task in the field of chemical biology and drug delivery. Recently, we reported synthesis of racemic stimulus-responsive amino acids and their application for controlling peptidyl function. In this study, we report enantioselective synthesis of a key intermediate of stimulus-responsive amino acids via asymmetric α-amination reaction of an aldehyde. The obtained chiral intermediate was converted to an Fmoc protected UV-responsive amino acid with (S)-configuration, and it was successfully incorporated into a model peptide by Fmoc solid phase peptide synthesis.

Journal

  • Tetrahedron

    Tetrahedron 66(37), 7367-7372, 2010-07-21

    Elsevier Ltd.

Codes

  • NII Article ID (NAID)
    120006493355
  • NII NACSIS-CAT ID (NCID)
    AA00861787
  • Text Lang
    ENG
  • Article Type
    journal article
  • ISSN
    0040-4020
  • Data Source
    IR 
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