Complestatin synthetic studies; the effect of the amino acid configuration on peptide backbone conformation in the common western BCD macrocycle.
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.
Smith
Amos B
AB
Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104-6323, USA. smithab@sas.upenn.edu
Chruma
Jason J
JJ
Han
Qiang
Q
Barbosa
Joseph
J
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
D000596:Amino Acids; D002733:Chlorophenols; D006571:Heterocyclic Compounds; D010455:Peptides; D010456:Peptides, Cyclic; C023490:complestatin