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Fluoroproline Flip‐Flop: Regiochemical Reversal of a Stereoelectronic Effect on Peptide and Protein Structures
Author(s) -
Kim Wookhyun,
Hardcastle Kenneth I.,
Conticello Vincent P.
Publication year - 2006
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.200603227
Subject(s) - flip flop , flip , peptide , stereochemistry , chemistry , materials science , biochemistry , optoelectronics , apoptosis , cmos
Pucker up! Structural analysis of the epimeric N ‐acetyl‐(2 R ,3 R )‐ and N ‐acetyl‐(2 R ,3 S )‐3‐fluoroproline methyl esters ( 1 and 2 ; see scheme) reveals opposing ring puckers that invert the conformational preferences of the corresponding 4‐fluoroproline derivatives 3 and 4 . Substitution of these fluoroprolines into proteins provides a method for controlling local conformation through stereoelectronic and steric effects.