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Amino Acids

, Volume 38, Issue 1, pp 133–143 | Cite as

A preparation of N-Fmoc-N-methyl-α-amino acids and N-nosyl-N-methyl-α-amino acids

  • Maria Luisa Di Gioia
  • Antonella Leggio
  • Angelo LiguoriEmail author
  • Francesca Perri
  • Carlo Siciliano
  • Maria Caterina Viscomi
Original Article

Abstract

A convenient route for the synthesis of lipophilic N-Fmoc-N-methyl-α-amino acids and N-nosyl-N-methyl-α-amino acids, interesting building blocks to be used for the preparation of N-methylated peptides, is presented. Both nosyl- and Fmoc-protected monomers are accessible, so these compounds can be used in solution as well as in solid phase peptide synthesis. The methodology is based on the use of benzhydryl group to protect temporarily the carboxyl function of N-nosyl-α-amino acids and on the subsequent methylation of the N-nosyl-α-amino acid benzhydryl esters with diazomethane. The benzhydryl esters offer several beneficial features such as simple preparation, stability to methylation and selective deprotection under mild conditions. The overall procedure is highly efficient in that the adopted conditions keep the chiral integrity of amino acid precursors and the process does not require chromatographic purification of the methylated products.

Keywords

N-Fmoc-N-methyl-α-amino acid N-Methyl-N-nosyl-α-amino acid Benzhydryl esters Diazomethane Diphenyldiazomethane N-Methylated dipeptides 

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Copyright information

© Springer-Verlag 2008

Authors and Affiliations

  • Maria Luisa Di Gioia
    • 1
  • Antonella Leggio
    • 1
  • Angelo Liguori
    • 1
    Email author
  • Francesca Perri
    • 1
  • Carlo Siciliano
    • 1
  • Maria Caterina Viscomi
    • 1
  1. 1.Dipartimento di Scienze FarmaceuticheUniversità della CalabriaArcavacata di Rende (CS)Italy

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