title: A modular synthetic approach toward exhaustively stereodiversified ligand libraries.
abstract: [structure] This report describes a modular approach to the synthesis of stereodiversified natural product-like libraries. Monomers 2 and 3 were coupled in parallel by silyl-tethered olefin metathesis to generate all 16 stereoisomers of cis-enediols 1. All 16 stereoisomers were incorporated into chimerae having flanking peptidic segments. These chimerae exhibited a broad range of hydrophobicities, raising the possibility that stereochemical variation might be used to tune the pharmacologic properties of small molecules.
authors: Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.
authors: T M
authors: TM
authors: Gierasch
authors: M
authors: M
authors: Chytil
authors: M T
authors: MT
authors: Didiuk
authors: J Y
authors: JY
authors: Park
authors: J J
authors: JJ
authors: Urban
authors: S P
authors: SP
authors: Nolan
authors: G L
authors: GL
authors: Verdine
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis; D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D020650:Combinatorial Chemistry Techniques; D008024:Ligands; D010455:Peptides / Q000138:chemical synthesis; D012833:Siloxanes / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D008024:Ligands; D010455:Peptides; D012833:Siloxanes