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Conformational Properties of 4‐Mercaptoproline and Related Derivatives
Author(s) -
Cadamuro Sergio A.,
Reichold Rudolf,
Kusebauch Ulrike,
Musiol HansJürgen,
Renner Christian,
Tavan Paul,
Moroder Luis
Publication year - 2008
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.200704310
Subject(s) - steric effects , chemistry , hydroxyproline , epimer , proline , stereochemistry , non covalent interactions , chalcogen , amino acid , organic chemistry , molecule , biochemistry , hydrogen bond
Spot the difference : Conformational analysis of the 2 S ,4 R and 2 S ,4 S epimers of N ‐acetyl‐4‐mercaptopyrrolidine‐2‐carboxylic acid methyl esters reveals ring‐pucker preferences that are opposite of those of the hydroxyproline derivatives (see scheme). Replacement of proline or hydroxyproline in polypeptides with the chalcogen analogue should allow for fine‐tuning of the complex interplay of noncovalent interactions, steric hindrance, and stereoelectronic effects.