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Photo-Click-Heptanoic acid
Chemical name: 2-(3-(but-3-ynyl)-3H-diazirin-3-yl)acetic acid
- Product code:RL-3410
- CAS No.:2049109-24-0
- Formula:C7H8N2O2
- Storage temperature:-20°C
- Molecular weight:152.15 g/mol
from $562.50
description
Trifunctional cross-linker with for conjugation of nucleophiles, like amines, with azides or any other functional groups for click chemistry. This linker bears an additional azirin ring, which will dismiss N2 under illumination of UV light. The remaining carbene will undergo insertion and addition reaction with any neighboring molecules and irreversibly form a covalent bond.
references
Cross-linking chemistry and biology: development of multifunctional photoaffinity probes. Takenori Tomohiro, Makoto Hashimoto, Yasumaru Hatanaka; Chem. Record 2005; 5(6): 385-395. DOI: 10.1002/tcr.20058.
Recent Progress in Diazirine-Based Photoaffinity Labeling. Makoto Hashimoto, Yasumaru Hatanaka; Eur. J. Org. Chem. 2008; 2513-2523. DOI: 10.1002/ejoc.200701069.
Endeavors to Make the Photophore, Diazirine Easy to Use. Yutaka Sadakane; Yakugaku Zasshi 2007; 127(10): 1693-1699. DOI: org/10.1248/yakushi.127.1693.
Synthesis of ramariolide natural products and discovery of their targets in mycobacteria. Johannes Lehmann, Johannes Richers, Alexander Pöthig, Stephan A. Sieber; Chem. Commun. 2017; 53: 107-110. DOI: 10.1039/C6CC08365J.
A Whole Proteome Inventory of Background Photocrosslinker Binding. Kleiner P., Heydenreuter W., Stahl M., Korotkov V.S., Sieber S.A.; Angew Chem Int Ed Engl. 2017; 56(5): 1396-1401. DOI: 10.1002/anie.201605993.
Peptidoglycan Metabolite Photoaffinity Reporters Reveal Direct Binding to Intracellular Pattern Recognition Receptors and Arf GTPases. Wang Y.C., Westcott N.P., Griffin M.E., Hang H.C.;. ACS Chem Biol. 2019; 14(3): 405-414. DOI: 10.1021/acschembio.8b01038.
Cell- and Tissue-Based Proteome Profiling and Dual Imaging of Apoptosis Markers with Probes Derived from Venetoclax and Idasanutlin. Zhu D., Guo H., Chang Y., Ni Y., Li L., Zhang Z.M., Hao P., Xu Y., Ding K., Li Z; Angew Chem Int Ed Engl. 2018; 57(30): 9284-9289. DOI: 10.1002/anie.201802003.
Fishing for Drug Targets: A Focus on Diazirine Photoaffinity Probe Synthesis. James R. Hill, Avril A. B. Robertson; J. Med. Chem. 2018; 61: 6945−6963. DOI: 10.1021/acs.jmedchem.7b01561.
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