Proline editing: a divergent strategy for the synthesis of conformationally diverse peptides
Krista M Thomas1, Devan Naduthambi, Gasirat Tririya
1Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, USA.
Organic Letters
|June 4, 2005
Abstract:
[reaction: see text] Strong conformational biases in peptides and proteins can be achieved with 4-substituted proline residues (cis-, trans-, or disubstituted fluoroproline or hydroxyproline). The practical, divergent synthesis of peptides containing these residues, via postsynthetic modification of a peptide containing an internal trans-hydroxyproline residue, is described. Significant differences in the conformations of the peptides Ac-TYXN-NH2 were observed, including K(trans/cis) values, which varied from 1.5 (X = cis-fluoroproline) to 7.0 (X = trans-fluoroproline).
