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Bioorg Med Chem Lett. 2008 Feb 1;18(3):1096-101. Epub 2007 Dec 7.

Protected aminooxyprolines for expedited library synthesis: application to Tsg101-directed proline-oxime containing peptides.

Liu F, Stephen AG, Fisher RJ, Burke TR Jr.

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Laboratory of Medicinal Chemistry, CCR, NCI-Frederick, NIH, Building 376 Boyles Street, Frederick, MD 21702, USA.

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.

PMID:: 18083557; [PubMed - indexed for MEDLINE]
PMCID:: PMC2488393

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Cited by 5 PubMed Central articles

Elucidation of New Binding Interactions with the Tumor Susceptibility Gene 101 (Tsg101) Protein Using Modified HIV-1 Gag-p6 Derived Peptide Ligands. [ACS Med Chem Lett. 2011]
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