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Epimerization‐Free Block Synthesis of Peptides from Thioacids and Amines with the Sanger and Mukaiyama Reagents
Author(s) -
Crich David,
Sharma Indrajeet
Publication year - 2009
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200805782
Subject(s) - reagent , chemistry , amine gas treating , epimer , aryl , halide , combinatorial chemistry , peptide bond , peptide , stereochemistry , medicinal chemistry , organic chemistry , alkyl , biochemistry
Highly activated thioesters formed by the rapid reaction of C‐terminal thioacids derived from protected amino acids and peptides with the Sanger reagent and other electron‐deficient aryl halides in the presence of a free amine immediately form a peptide bond with the amine. This essentially epimerization‐free method was used for the 4+4 block synthesis of a hindered octapeptide (see scheme; Boc, Pbf, and Trt are protecting groups).