A tripodal peptidic titanium phosphonate as a homochiral porous solid medium for the heterogeneous enantioselective hydration of epoxides

Anat Milo, Ronny Neumann

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

A porous, homochiral titanium-phosphonate material based on a tripodal peptide scaffold was used as a heterogeneous reaction medium for the enantioselective hydration (>99%) of styrene oxide. This titanium-phosphonate material, which was shown to contain confined chiral spaces, was prepared by polymerization of L-leucine onto a tris(2-aminoethyl)amine initiator, followed by capping with phosphonate groups and completed by non-aqueous condensation with titanium isopropoxide. Circular dichroism confirmed that the peptide tethers yielded a secondary structure. X-ray powder diffraction and transmission electron microscopy supported by a semi-empirical model showed the likely formation of a porous, lamellar material that was quantified by nitrogen adsorption.

Original languageEnglish
Pages (from-to)2159-2165
Number of pages7
JournalAdvanced Synthesis and Catalysis
Volume352
Issue number13
DOIs
Publication statusPublished - Sep 10 2010

Fingerprint

Organophosphonates
Epoxy Compounds
Titanium
Hydration
styrene oxide
Peptides
Dichroism
Scaffolds (biology)
Scaffolds
Leucine
X ray powder diffraction
Styrene
Condensation
Amines
Nitrogen
Polymerization
Transmission electron microscopy
Adsorption
Oxides

Keywords

  • Catalyst design
  • Enantioselectivity
  • Hydrolysis
  • Organic-inorganic composites
  • Peptides

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

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AB - A porous, homochiral titanium-phosphonate material based on a tripodal peptide scaffold was used as a heterogeneous reaction medium for the enantioselective hydration (>99%) of styrene oxide. This titanium-phosphonate material, which was shown to contain confined chiral spaces, was prepared by polymerization of L-leucine onto a tris(2-aminoethyl)amine initiator, followed by capping with phosphonate groups and completed by non-aqueous condensation with titanium isopropoxide. Circular dichroism confirmed that the peptide tethers yielded a secondary structure. X-ray powder diffraction and transmission electron microscopy supported by a semi-empirical model showed the likely formation of a porous, lamellar material that was quantified by nitrogen adsorption.

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