Protected aminooxyprolines for expedited library synthesis: application to Tsg101-directed proline-oxime containing peptides.
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.
Liu
Fa
F
Laboratory of Medicinal Chemistry, CCR, NCI-Frederick, NIH, Building 376 Boyles Street, Frederick, MD 21702, USA.
Stephen
Andrew G
AG
Fisher
Robert J
RJ
Burke
Terrence R
TR
D000447:Aldehydes / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D004268:DNA-Binding Proteins / Q000737:chemistry / Q000378:metabolism*; D056827:Endosomal Sorting Complexes Required for Transport; D006801:Humans; D015394:Molecular Structure; D010091:Oximes / Q000138:chemical synthesis* / Q000737:chemistry; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D011392:Proline / Q000737:chemistry*; D011487:Protein Conformation; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014157:Transcription Factors / Q000737:chemistry / Q000378:metabolism*; D000099177:Tsg101 Protein
D000447:Aldehydes; D004268:DNA-Binding Proteins; D056827:Endosomal Sorting Complexes Required for Transport; D010091:Oximes; D010455:Peptides; D011392:Proline; D014157:Transcription Factors; D000099177:Tsg101 Protein