For research use only. Not for therapeutic Use.
Dansylamide functionalized PEG-phenylboronic acid for the use of palladium-catalyzed oxidative Heck reaction to protein-bound alkenes and Suzuki-Miyaura cross coupling for labeling of protein bound phenylhalides in high yields and with excellent chemoselectivity. Reagent for bio-orthogonal protein-ligation.*Sold in collaboration with RuG (University of Groningen)
| Catalog Number | I047604 |
| CAS Number | 1661014-49-8 |
| Molecular Formula | C30H41BN4O9S |
| Purity | ≥95% |
| IUPAC Name | [3-[[4-[2-[2-[2-[2-[[5-(dimethylamino)naphthalen-1-yl]sulfonylamino]ethoxy]ethoxy]ethoxy]ethylamino]-4-oxobutanoyl]amino]phenyl]boronic acid |
| InChI | InChI=1S/C30H41BN4O9S/c1-35(2)27-10-4-9-26-25(27)8-5-11-28(26)45(40,41)33-15-17-43-19-21-44-20-18-42-16-14-32-29(36)12-13-30(37)34-24-7-3-6-23(22-24)31(38)39/h3-11,22,33,38-39H,12-21H2,1-2H3,(H,32,36)(H,34,37) |
| SMILES | B(C1=CC(=CC=C1)NC(=O)CCC(=O)NCCOCCOCCOCCNS(=O)(=O)C2=CC=CC3=C2C=CC=C3N(C)C)(O)O |
| Reference | 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. |
