SYNTHESIS OF p‐AMINO‐L‐PHENYLALANINE DERIVATIVES WITH PROTECTED p‐AMINO GROUP FOR PREPARATION OF p‐AZIDO‐L‐PHENYLALANINE PEPTIDES
- 1 April 1980
- journal article
- research article
- Published by Wiley in International Journal of Peptide and Protein Research
- Vol. 15 (4) , 323-330
- https://doi.org/10.1111/j.1399-3011.1980.tb02908.x
Abstract
For affinity labeling of peptide hormone receptors, the use of peptides containing p-azidophenylalanine is desired. 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 Cu complex or by specific acylation at pH 4.6. The .alpha.-amino or .alpha.-carboxy group is blocked by a protecting group (Boc [butoxycarbonyl], Ddz [3,5-dimethoxy-.alpha.,.alpha.-dimethylbenzyloxycarbonyl], OMe, respectively, Z [benzyloxycarbonyl], Nps [p-nitrophenylthio], Ddz), which can be removed selectively. The synthesis of 9 derivatives of p-amino-L-phenylalanine for incorporation into the peptide chain is described. The p-amino-phenylalanine is converted to p-azidophenyalanine without affecting disulfide bridges.Keywords
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