Conformational Properties of 4‐Mercaptoproline and Related Derivatives

Abstract

Spot the difference: Conformational analysis of the 2S,4R and 2S,4S 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. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2008/z704310_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.