Abstract
The stereoselective synthesis of aminooxy-containing proline analogues bearing Fmoc/Boc or Fmoc/Mtt protection that renders them suitable for incorporation into peptides using Fmoc protocols is reported. Acid-catalyzed unmasking at the completion of peptide synthesis yields free aminooxy-functionalities for oxime formation through reaction with libraries of aldehydes. This allows post solid-phase diversification strategies that may facilitate structure-activity relationship studies.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, N.I.H., Intramural
MeSH terms
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Aldehydes / chemistry
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Combinatorial Chemistry Techniques*
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DNA-Binding Proteins / chemistry
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DNA-Binding Proteins / metabolism*
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Endosomal Sorting Complexes Required for Transport
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Humans
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Molecular Structure
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Oximes / chemical synthesis*
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Oximes / chemistry
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Peptides / chemical synthesis*
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Peptides / chemistry
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Proline / chemistry*
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Protein Conformation
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Stereoisomerism
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Structure-Activity Relationship
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Transcription Factors / chemistry
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Transcription Factors / metabolism*
Substances
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Aldehydes
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DNA-Binding Proteins
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Endosomal Sorting Complexes Required for Transport
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Oximes
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Peptides
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Transcription Factors
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Tsg101 protein
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Proline