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DecarboxyBiotin-N3
Chemical name: (3aS,4S,6aR)- 4-(5-Azidopentyl)tetrahydro-1H-Thieno[3,4-d]imidazol-2(3H)-one
- Product code:LS-4300
- CAS No.:1260586-88-6
- Formula:C10H17N5OS
- Storage temperature:2-8°C
- Molecular weight:255,34 g/mol
from €600.00
description
This biotin derivative bears a terminal azide group. It can be used to prepare various biotinylated conjugates via Click Chemistry. Biotin can be subsequently detected e.g. via streptavidin or avidin. Triazole-linked adducts are showen to be highly resistant to the ubiquitous hydrolytic enzyme biotinidase and to bind avidin with dissociation constants in the low pM range.
references
Probing biotin receptors in cancer cells with rationally designed fluorogenic squaraine dimers; K. T. Fam, M. Collot, A. S. Klymchenko; Chem. Sci. 2020; 11: 8240-8248. https://doi.org/10.1039/D0SC01973A.
Biotin-tagged fluorescent sensor to visualize ‘mobile’ Zn2+ in cancer cells; L. Fang, G. Trigiante, C. J. Kousseff, R. Crespo-Otero, M. P. Philpott, M. Watkinson; Chem. Commun. 2018; 54: 9619-9622. https://doi.org/10.1039/C8CC05425H.
Surface-enhanced Raman encoded polymer stabilized gold nanoparticles: Demonstration of potential for use in bioassays; T. L. Schiller, D. J. Keddie, I. Blakey, P. M. Fredericks; Eur. Polym. J. 2017; 87: 508-518. https://doi.org/10.1016/j.eurpolymj.2016.08.032.
A versatile platform for adding functional properties to amyloid fibrils; D. F. A. Fontaine, V. A. Ivancic, M. B. Reardon, N. D. Lazo, C. E. Jakobsche; Org. Biomol. Chem. 2017; 15: 8023-8027. https://doi.org/10.1039/C7OB02042B.
Heterocyclic acyl-phosphate bioisostere-based inhibitors of Staphylococcus aureus biotin protein ligase; W. Tieu, A. M. Jarrad, A. S. Paparella, K. A. Keeling, T. P. Soares da Costa, J. C. Wallace, G. W. Booker, S. W. Polyak, A. D. Abell; Bioorg. Med. Chem. Lett. 2014; 24(19): 4689-4693. https://doi.org/10.1016/j.bmcl.2014.08.030.
Triazole biotin: a tight-binding biotinidase-resistant conjugate; A. I. Germeroth, J. R. Hanna, R. Karim, F. Kundel, J. Lowther, P. G. N. Neate, E. A. Blackburn, M. A. Wear, D. J. Campopiano, A. N. Hulme; Org. Biomol. Chem. 2013; 11: 7700-7704. https://doi.org/10.1039/C3OB41837E.
A Photocleavable Rapamycin Conjugate for Spatiotemporal Control of Small GTPase Activity; N. Umeda, T. Ueno, C. Pohlmeyer, T. Nagano, T. Inoue; J. Am. Chem. Soc. 2011; 133(1): 12-14. https://doi.org/10.1021/ja108258d.
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