Diazo Biotin-PEG3-alkyne

• CAT Number: I014328
• CAS Number: 1884349-58-9
• Molecular Formula: C39H53N7O9S
• Molecular Weight: 795.95
• Purity: ≥95%
• Synonyms: Diazo Biotin-PEG3-alkyne;4-(2-(2-hydroxy-5-(2-(3-(prop-2-yn-1-yloxy)propanamido)ethyl)phenyl)-1l2,2l2-diazanyl)-N-(13-oxo-17-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)-3,6,9-trioxa-12-azaheptadecyl)benzamide
• Target: PROTAC Linkers
• Solubility: Soluble in DMSO
• InChI: InChI=1S/C39H53N7O9S/c1-2-18-52-19-14-36(49)40-15-13-28-7-12-33(47)31(26-28)46-45-30-10-8-29(9-11-30)38(50)42-17-21-54-23-25-55-24-22-53-20-16-41-35(48)6-4-3-5-34-37-32(27-56-34)43-39(51)44-37/h1,7-12,26,32,34,37,47H,3-6,13-25,27H2,(H,40,49)(H,41,48)(H,42,50)(H2,43,44,51)/t32-,34-,37-/m0/s1
• InChIKey: AIUZFZDETVBCLH-OHTDSXDOSA-N
• SMILES: O=C1N[C@@]2([H])CS[C@@H](CCCCC(NCCOCCOCCOCCNC(C3=CC=C([N][N]C4=CC(CCNC(CCOCC#C)=O)=CC=C4O)C=C3)=O)=O)[C@@]2([H])N1

Diazo Biotin-PEG3-alkyne is useful for introducing a biotin moiety to azide-containing biomolecules using Cu(I)-catalyzed Click Chemistry. The hydrophilic spacer arm provides better solubility to the labeled molecules in aqueous media. Diazo allows efficient release of captured biotinylated molecules from streptavidin using sodium dithionite (Na2S2O4).

Reference

1: Deng CY, Long YY, Liu S, Chen ZB, Li C. [Construction of biotin-modified polymeric micelles for pancreatic cancer targeted photodynamic therapy]. Yao Xue Xue Bao. 2015 Aug;50(8):1038-44. Chinese. PubMed PMID: 26669006.2: Zhu W, Song Z, Wei P, Meng N, Teng F, Yang F, Liu N, Feng R. Y-shaped biotin-conjugated poly (ethylene glycol)-poly (epsilon-caprolactone) copolymer for the targeted delivery of curcumin. J Colloid Interface Sci. 2015 Apr 1;443:1-7. doi: 10.1016/j.jcis.2014.11.073. Epub 2014 Dec 6. PubMed PMID: 25526295.3: Ke S, Wright JC, Kwon GS. Avidin-biotin-PEG-CPA complexes as potential EPR-directed therapeutic protein carriers: preparation and characterization. Bioconjug Chem. 2007 Sep-Oct;18(5):1644-50. Epub 2007 Aug 18. PubMed PMID: 17705554.4: Kaiser K, Marek M, Haselgrübler T, Schindler H, Gruber HJ. Basic studies on heterobifunctional biotin-PEG conjugates with a 3-(4-pyridyldithio)propionyl marker on the second terminus. Bioconjug Chem. 1997 Jul-Aug;8(4):545-51. PubMed PMID: 9258454.