title: Complestatin synthetic studies; the effect of the amino acid configuration on peptide backbone conformation in the common western BCD macrocycle.
abstract: The synthesis and structural analysis, involving X-ray crystallographic, nuclear magnetic resonance, and computational studies of four diastereomers of the common western BCD diarylether macrocycle of the complestatins, a family of HIV entry inhibitors, has been achieved exploiting a ruthenium-promoted intramolecular S(N)Ar reaction. The stereogenicity of the individual phenylglycines (residues C and D) results in remarkable effects on the backbone conformation.
authors.affiliation: Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104-6323, USA. smithab@sas.upenn.edu
authors.forename: Amos B
authors.initials: AB
authors.lastname: Smith
authors.forename: Jason J
authors.initials: JJ
authors.lastname: Chruma
authors.forename: Qiang
authors.initials: Q
authors.lastname: Han
authors.forename: Joseph
authors.initials: J
authors.lastname: Barbosa
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D002733:Chlorophenols / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry; D008958:Models, Molecular; D010455:Peptides / Q000737:chemistry; D010456:Peptides, Cyclic / Q000737:chemistry*; D011487:Protein Conformation
chemical_list: D000596:Amino Acids; D002733:Chlorophenols; D006571:Heterocyclic Compounds; D010455:Peptides; D010456:Peptides, Cyclic; C023490:complestatin