A modular synthetic approach toward exhaustively stereodiversified ligand libraries

T M Gierasch, M Chytil, M T Didiuk, J Y Park, J J Urban, Steven Patrick Nolan, G L Verdine

Research output: Contribution to journalArticlepeer-review

40 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)3999-4002
Number of pages4
JournalOrganic Letters
Volume2
Issue number25
Publication statusPublished - 14 Dec 2000

Keywords

  • RING-CLOSING METATHESIS
  • PEPTIDE COMBINATORIAL LIBRARIES
  • OLEFIN METATHESIS
  • ORGANIC-SYNTHESIS
  • DRUG DISCOVERY
  • POLYKETIDE LIBRARIES
  • RUCL2(=CHR')(PR(3))(2)
  • PEPTIDOMIMETICS
  • TECHNOLOGIES
  • DIVERSITY

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