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

Evangelos E. Bissyris; Dimitris Belekos; Vassiliki Magafa; Petros G. Tsoungas; George Varvounis; Paul Cordopatis

doi:10.1055/s-2005-918426

PAPER

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

Evangelos E. Bissyris^a, Dimitris Belekos^b, Vassiliki Magafa^a, Petros G. Tsoungas^c, 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

Abstract

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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

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References

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