Please use this identifier to cite or link to this item: http://scholarbank.nus.edu.sg/handle/10635/14323
Title: Facile synthesis of combinatorial vinyl sulfone libraries and their applications in large scale proteomics
Authors: WANG GANG
Keywords: vinyl sulfone, cysteine protease, solid phase, activity-based probe,
Issue Date: 20-Oct-2004
Source: WANG GANG (2004-10-20). Facile synthesis of combinatorial vinyl sulfone libraries and their applications in large scale proteomics. ScholarBank@NUS Repository.
Abstract: A series of vinyl sulfone compounds were synthesized using either solution phase or solid phase synthesis strategies. First a peptide vinyl sulfone probe was prepared in solution and used as an activity-based probe in profiling cysteine protease. Next we developed facile and efficient solid phase strategies for the synthesis of combinatorial library of vinyl sulfone-containing, activity-based probes of cysteine proteases Our first solid-phase strategy was based on the synthesis and immobilization of phenolic-Fmoc-amino-vinyl sulfones onto 2-Cl-Trityl chloride resin, followed by peptide synthesis and probe generation. Our second strategy took advantage of the successful implementation of both solid phase oxidation and Horner-Wadsworth-Emmons reaction, and this strategy was used for the synthesis of combinatorial library of vinyl sulfone probes having 20 variations at P1 position. We also successful synthesized of a 30-member vinyl sulfone small molecule library having three points of diversity (P1, P2 and P1a??) within the vinyl sulfone scaffold.
URI: http://scholarbank.nus.edu.sg/handle/10635/14323
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