title: An investigation into the origin of the dramatically reduced reactivity of peptide-prolyl-thioesters in native chemical ligation.
abstract: The low reactivity of peptide-prolyl-thioesters in native chemical ligation is not due to steric effects at the β-carbon, but rather to the presence of a carbonyl moiety on the nitrogen atom of the proline.
authors.affiliation: Department of Chemistry, Institute for Biophysical Dynamics, The University of Chicago, Chicago, Illinois 60637, USA.
authors.forename: Samuel B
authors.initials: SB
authors.lastname: Pollock
authors.forename: Stephen B H
authors.initials: SB
authors.lastname: Kent
mesh_terms: D000595:Amino Acid Sequence; D006860:Hydrogen Bonding; D010455:Peptides / Q000737:chemistry*; D011392:Proline / Q000737:chemistry*
chemical_list: D010455:Peptides; D011392:Proline