Synthesis of p-amino-L-phenylalanine derivatives with protected p-amino group 
for preparation of p-azido-L-phenylalanine peptide

Fahrenholz, Falk; Thierauch, Karl-Heinz

doi:10.1111/j.1399-3011.1980.tb02908.x

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Synthesis of p-amino-L-phenylalanine derivatives with protected p-amino group for preparation of p-azido-L-phenylalanine peptide

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Fahrenholz, Falk
Department of Physical Chemistry, Max Planck Institute of Biophysics, Max Planck Society;

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Thierauch, Karl-Heinz
Department of Physical Chemistry, Max Planck Institute of Biophysics, Max Planck Society;

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Citation

Fahrenholz, F., & Thierauch, K.-H. (1980). Synthesis of p-amino-L-phenylalanine derivatives with protected p-amino group for preparation of p-azido-L-phenylalanine peptide. International journal of peptide and protein research, 15(4), 323-330. doi:10.1111/j.1399-3011.1980.tb02908.x.

Cite as: https://hdl.handle.net/21.11116/0000-0008-3E8A-8

Abstract

For the synthesis of p-azidophenylalanine peptides, the p-amino group of p-amino-L-phenylalanine is protected with the Z- or Boc residue via the copper complex or by specific acylation at pH 4.6. The alpha-amino or alpha-carboxy group is blocked by a protecting group (Boc, Ddz, OMe respectively Z, Nps, Ddz), which can be removed selectively. The synthesis of nine derivatives of p-amino-L-phenylalanine for incorporation into the peptide chain is described. The p-amino-phenylalanine is converted to p-azidophenylalanine without affecting disulfide bridges.