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Efficient, Optimized Applications of p ‐Nitrophenyl Active Ester Temporarily Protecting Groups Together with Simultaneous Activation in Synthesis of Special Glu and Lys Peptides
Author(s) -
Szókán Gy.,
Almás M.,
Kótai A.,
Khlafulla A. R.
Publication year - 1997
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.199700079
Subject(s) - chemistry , aminolysis , ethylamine , peptide , protecting group , amino acid , peptide synthesis , combinatorial chemistry , azide , organic chemistry , biochemistry , catalysis , alkyl
Benzyloxycarbonyl‐glutamylpeptide p ‐nitrophenylesters were prepared from protected amino acids, e.g.: p ‐nitrophenyl‐glutamate as carboxyl component and aminoacid or peptide p ‐nitrophenylesters as amino components by different kinds of peptide coupling methods. Mixed carbonic anhydride and azide methods gave good results. The p ‐nitrophenylesters existed as temporary protecting groups, so the peptide couplings proceeded together with simultaneous activation. The conditions and applications of the procedure are discussed. The peptides having one or more active ester groups were used to form amides by their aminolysis with derivatives of ethylamine or were polycondensated (after deprotection) to obtain polypeptides.