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Convenient Synthesis of N ‐Terminal Tfm‐Dipeptides from Unprotected Enantiopure α‐Tfm‐Proline and α‐Tfm‐Alanine
Author(s) -
Chaume Grégory,
Lensen Nathalie,
Caupène Caroline,
Brigaud Thierry
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900768
Subject(s) - enantiopure drug , chemistry , dipeptide , diketopiperazines , tripeptide , amino acid , alanine , trifluoromethyl , stereochemistry , proline , peptide synthesis , coupling reaction , combinatorial chemistry , organic chemistry , enantioselective synthesis , catalysis , biochemistry , alkyl
A convenient procedure for the synthesis of highly lipophilic dipeptide building blocks from enantiopure α‐trifluoromethyl α‐amino acids is reported. Coupling reactions at the C termini of the trifluoromethyl α‐amino acids were successfully performed with totally unprotected amino acids without formation of diketopiperazines. The synthesis of a tripeptide through a coupling reaction at the deactivated N‐terminal position was achieved. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)