Proline editing: a divergent strategy for the synthesis of conformationally diverse peptides.
[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).
Thomas
Krista M
KM
Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, USA.
Naduthambi
Devan
D
Tririya
Gasirat
G
Zondlo
Neal J
NJ
D002851:Chromatography, High Pressure Liquid; D008958:Models, Molecular; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D011392:Proline / Q000737:chemistry*; D011487:Protein Conformation
D010455:Peptides; D011392:Proline