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Library Screening in Aqueous Media To Develop a Highly Active Peptide Catalyst for Enantioselective Michael Addition of a Malonate
Author(s) -
Akagawa Kengo,
Iwasaki Yumika,
Kudo Kazuaki
Publication year - 2016
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.201600828
Subject(s) - chemistry , enantioselective synthesis , malonate , peptide , michael reaction , catalysis , residue (chemistry) , lysine , aqueous solution , proline , tryptophan , stereochemistry , combinatorial chemistry , organocatalysis , organic chemistry , amino acid , biochemistry
Screenings of peptide libraries with N‐terminal l ‐ or d ‐proline were performed under aqueous conditions to obtain capable catalysts for the asymmetric Michael addition of a malonate. From a d ‐prolyl peptide library, a consensus sequence, d ‐Pro‐ d ‐Pro‐X‐Trp‐X 3 , was found, and the peptide possessing lysine in this framework showed good reactivity and enantioselectivity. The presence of the tryptophan residue at the fourth position was essential and replacing it with a pyrenylalanine residue further improved the catalytic ability. With an optimum peptide, the reaction could be promoted efficiently in aqueous media at a low catalyst loading.