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The L ‐Leu Hexamer, a Short and Highly Enantioselective Peptide Catalyst for the Juliá–Colonna Epoxidation: Stabilization of a Helical Conformation in DMSO
Author(s) -
Weyer Alexandra,
Díaz Dolores,
Nierth Alexander,
Schlörer Nils E.,
Berkessel Albrecht
Publication year - 2012
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201100243
Subject(s) - random hexamer , enantioselective synthesis , peptide , chemistry , catalysis , stereochemistry , helix (gastropod) , combinatorial chemistry , nuclear magnetic resonance spectroscopy , crystallography , organic chemistry , biochemistry , ecology , snail , biology
A short peptide throws long shadows: As revealed by NMR spectroscopy, L ‐Leu 6 , one of the shortest peptides active as a catalyst in the Juliá–Colonna (JC) asymmetric epoxidation, forms a stable 3 10 ‐helix in DMSO. The structure supports the mechanistic model in which the N‐terminus acts as an oxyanion hole that interacts with the β‐hydroperoxyenolate intermediate of the JC reaction.