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

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Reetz,  M. T.
Research Department Reetz, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Research Department Reetz, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Research Department Reetz, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Rüggeberg,  C. J.
Research Department Reetz, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

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.


Cite as: http://hdl.handle.net/11858/00-001M-0000-000F-9983-4
Abstract
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.