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Synthesis 2005(18): 3159-3166
DOI: 10.1055/s-2005-918426
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
Further Information
Publication History
Received
6 June 2005
Publication Date:
06 October 2005 (online)


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