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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 35, Number 2
BKCSDE 35(2)
February 20, 2014 

Design, Synthesis and Preliminary Biological Evaluation of a Biotin-S-S-Phosphine Reagent
Dong W. Kang, Eun J. Kim*
Biotin, Avidin, Disulfide bond linker, Staudinger ligation, O-GlcNAc
Biotin-S-S-Phosphine was designed and synthesized as a potential tool for a proteomic study of O-GlcNAcmodified proteins. This reagent features a disulfide linker between a triarylphosphine moiety, which allows selective conjugation to azide-containing proteins, and a biotin moiety that can allow easy isolation through its strong affinity toward avidin-coated solid beads. The disulfide linkage within this reagent can allow the easy release of the bound molecules of interest, which is difficult to achieve when a biotin:avidin pair is used alone, by reducing the disulfide bond of the reagent with DTT. Preliminary in vitro biological assays with azidelabeled and unlabeled cell lysates and a pure protein Nup62 showed that the Biotin-S-S-Phosphine reagent is highly reactive toward the free thiol groups of proteins. When a molecular tool with a disulfide linker is applied to the enrichment of the molecules of interest from other species, it is important to block the free-thiols of the sample using exhaustive alkylation prior to the Staudinger ligation reactions to restore the bioorthogonal nature of this reaction.
383 - 391
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