jo100301n_si_001.pdf (9.36 MB)
Further Studies toward the Stereocontrolled Synthesis of Silicon-Containing Peptide Mimics
journal contribution
posted on 2010-05-21, 00:00 authored by Dácil Hernández, Karl B. Lindsay, Lone Nielsen, Tina Mittag, Klaus Bjerglund, Stig Friis, Rasmus Mose, Troels SkrydstrupFurther studies are reported on the utilization of the versatile reaction between chiral sulfinimines and alkyldiphenylsilyl lithium reagents with the goal of preparing a wide range of silanediol-based protease inhibitors. In particular, focus has been placed to demonstrate how a number of genetically encoded amino acid side chains such as serine, threonine, tyrosine, lysine, proline, arginine, aspartate and asparagine might be incorporated into the overall approach. Efforts to apply this synthetic methodology for accessing biologically relevant silanediol dipeptide mimics are also described. This includes the synthesis of a potential inhibitor of the human neutrophil elastase, as well as a diphenylsilane mimic of a hexapeptide fragment of the human islet amyloid polypeptide.
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neutrophil elastaseproteasefocusacid side chainsasparagineMimicsFurtheraspartatelysinesynthesisPeptideutilizationmethodologyprolineStereocontrolled Synthesisserineaccessingislet amyloid polypeptidehexapeptide fragmentarginineEffortsthreoninechiral sulfiniminessilanediol dipeptide mimicsapproachalkyldiphenylsilyl lithium reagentsdiphenylsilanetyrosineinhibitor
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