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Synthesis 2005(18): 3159-3166  
DOI: 10.1055/s-2005-918426
PAPER
© Georg Thieme Verlag Stuttgart · New York

2-Amino-4-pyrrolidinothieno[2,3-d]pyrimidine-6-carboxylic Acid as an N-Terminal Surrogate in Amino Acid and Peptide Analogues

Evangelos E. Bissyrisa, Dimitris Belekosb, Vassiliki Magafaa, Petros G. Tsoungasc, George Varvounis*b, Paul Cordopatis*a
a Department of Pharmacy, University of Patras, Rio 26504, Greece
Fax: +30(2610)997714; e-Mail: pacord@upatras.gr;
b Department of Chemistry, University of Ioannina, Ioannina 45110, Greece
Fax: +30(26510)98799; e-Mail: gvarvoun@cc.uoi.gr;
c Ministry of Development, Department of Research and Technology, 14-18 Messogion Ave., Athens 11510, Greece
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Publication History

Received 6 June 2005
Publication Date:
06 October 2005 (online)

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Abstract

2-Amino-4-pyrrolidinothieno[2,3-d]pyrimidine-6-carboxylic acid (4) (ATPC) is an unnatural amino acid with promise in applications as a building block for the synthesis of peptidomimetics. ATPC was obtained from both 3a and 3b thienopyrimidines by hydrolysis and hydrogenolysis, respectively. The synthesis of eleven ATPC-amino acids and two ATPC-peptides is described. ATPC is incorporated as N-terminal moiety in solution or solid-phase peptide synthesis using Boc or Fmoc methodology and without protection of the ATPC amino group.

Key words

heterocycles - amino acids - peptides - thienopyrimidine - angiotensin II