Further studies toward the stereocontrolled synthesis of silicon-containing peptide mimics

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaperJournal articleResearchpeer-review

  • Dácil Hernández
  • ,
  • Karl B Lindsay, Denmark
  • Lone Nielsen, Denmark
  • Tina Mittag, Denmark
  • Klaus Bjerglund, Denmark
  • Stig Friis, Denmark
  • Rasmus Mose, Denmark
  • Troels Skrydstrup
Further 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.
Original languageEnglish
JournalJournal of Organic Chemistry
Volume75
Issue10
Pages (from-to)3283-93
Number of pages11
ISSN0022-3263
DOIs
Publication statusPublished - 21 May 2010

    Research areas

  • Amino Acid Sequence, Humans, Leukocyte Elastase, Molecular Mimicry, Molecular Structure, Oligopeptides, Proteinase Inhibitory Proteins, Secretory, Silanes, Silicon, Stereoisomerism, Structure-Activity Relationship

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