title: Proline editing: a divergent strategy for the synthesis of conformationally diverse peptides.
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).
authors.affiliation: Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, USA.
authors.forename: Krista M
authors.initials: KM
authors.lastname: Thomas
authors.forename: Devan
authors.initials: D
authors.lastname: Naduthambi
authors.forename: Gasirat
authors.initials: G
authors.lastname: Tririya
authors.forename: Neal J
authors.initials: NJ
authors.lastname: Zondlo
mesh_terms: 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
chemical_list: D010455:Peptides; D011392:Proline