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  Immobilization of chiral enzyme inhibitors on solid supports by amide-forming coupling and olefin metathesis

Reetz, M. T., Rüggeberg, C. J., Dröge, M. J., & Quax, W. J. (2002). Immobilization of chiral enzyme inhibitors on solid supports by amide-forming coupling and olefin metathesis. Tetrahedron, 58(42), 8465-8473. doi:10.1016/S0040-4020(02)01052-9.

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 Urheber:
Reetz, M. T.1, Autor           
Rüggeberg, C. J.1, Autor           
Dröge, M. J.2, Autor
Quax, W. J.2, Autor
Affiliations:
1Research Department Reetz, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445588              
2Univ Groningen, Ctr Pharm, Dept Pharmaceut Biol, NL-9713 AV Groningen, Netherlands, ou_persistent22              

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Schlagwörter: biotransformations; olefin metathesis; asymmetric catalysis; lipase; phage display
 Zusammenfassung: The question whether phage display can be used as a selection method in the directed evolution of enantioselective enzymes has not been answered satisfactorily to date. In order to be able to test this in a specific case, namely in the hydrolytic kinetic resolution of the acetate derived from alpha,beta- isopropylideneglycerol (IPG) catalyzed by the lipase from Bacillus subtilis, suicide enzyme inhibitors anchored on porous glass or polymer beads were designed and synthesized. These are immobilized phosphonates, which bear a leaving group and also contain the chiral substrate (D) and (L)-IPG, Modified SIRAN((R)) (porous glass) and Tentagel((R)) (polymer) were chosen as carriers, attachment occurring via amide-forming coupling or Ru-catalyzed olefin metathesis. Initial lipase inhibition studies are also reported. (C) 2002 Elsevier Science Ltd. All rights reserved.

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Sprache(n): eng - English
 Datum: 2002-10-14
 Publikationsstatus: Erschienen
 Seiten: -
 Ort, Verlag, Ausgabe: -
 Inhaltsverzeichnis: -
 Art der Begutachtung: Expertenbegutachtung
 Identifikatoren: eDoc: 20470
DOI: 10.1016/S0040-4020(02)01052-9
ISI: 000178624700010
 Art des Abschluß: -

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Titel: Tetrahedron
  Alternativer Titel : Tetrahedron
Genre der Quelle: Zeitschrift
 Urheber:
Affiliations:
Ort, Verlag, Ausgabe: -
Seiten: - Band / Heft: 58 (42) Artikelnummer: - Start- / Endseite: 8465 - 8473 Identifikator: ISSN: 0040-4020