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Biotinyl-phenylboronic acid
- Optical Purity: Optically pure
- Soluble in 0.1N NaOH(aq), DMSO and MeOH
- MF: C16H22BN3O4S
- MW: 363.24
Description
Biotinyl-phenylboronic acid is a biotin-functionalized arylboronic acid reagent designed for bioorthogonal protein labeling through palladium-catalyzed oxidative Heck reactions with protein-bound alkenes and Suzuki-Miyaura cross-coupling with protein-bound phenylhalides. The biotin tag enables streptavidin-based detection or enrichment.
Chemoselective bioconjugation reagents are important tools for protein derivatization, biomarker detection and chemoproteomics workflows. Biotinyl-phenylboronic acid supports high-yield protein labeling under conditions compatible with selective downstream detection.
Key Features
- Biotinylated arylboronic acid labeling reagent
- Supports oxidative Heck and Suzuki-Miyaura protein labeling
- Enables streptavidin-based detection and enrichment
- Developed for bioorthogonal protein ligation workflows
Applications
- Protein labeling and derivatization
- Chemoproteomics enrichment assays
- Biomarker detection workflows
- Bioorthogonal coupling-method development
Note: *Sold in collaboration with the RUG (University of Groningen)
More Information
| Parent CAS No. | 1661014-48-7 |
|---|---|
| Chemical Name | 3-(5-((4S)-2-Oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido)phenylboronic acid |
| extra_info | Sold in collaboration with RuG (University of Groningen) |
| SMILES | C1C(B(O)O)=CC(NC(=O)CCCC[C@H]2C3NC(=O)NC3CS2)=CC=1 |&1:14,r| |
| MFCD | N.A. |
| InChi | InChI=1S/C16H22BN3O4S/c21-14(18-11-5-3-4-10(8-11)17(23)24)7-2-1-6-13-15-12(9-25-13)19-16(22)20-15/h3-5,8,12-13,15,23-24H,1-2,6-7,9H2,(H,18,21)(H2,19,20,22) |
| InChiKey | XTAZPFOELSKBQD-UHFFFAOYSA-N |
| CID | 24992892 |
| Short Description | Protein labeling reagent |
References
- ME Ourailidou et al. Aqueous oxidative Heck reaction as a protein-labeling strategy. Chembiochem. 2014, 15, 209-212.
- F D'Hooge et al. Biotinylated boronic acid fluorophore conjugates: Quencher elimination strategy for imaging and saccharide detection. RSC Adv. 2012, 2, 3274-3280.
- Chalker et al. A Convenient Catalyst for Aqueous and Protein Suzuki-Miyaura Cross-Coupling J. Am. Chem. Soc. 2009, 131, 16346-16347
- C.D. Spicer et al. Palladium-mediated site-selective Suzuki-Miyaura protein modification at genetically encoded aryl halides. Chem. Commun. 2011, 47, 1698-700
- C.D. Spicer et al. Palladium-mediated cell-surface labeling. J. Am. Chem. Soc. 2012, 134(2), 800-3.
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