Chemistry:Photobiotin

Photobiotin

Names
IUPAC name N-{3-[{3-[(4-Azido-2-nitrophenyl)amino]propyl}(methyl)amino]propyl}-5-[(3aS,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanamide
Other names Photoprobe biotin, Photoactivatable biotin
Identifiers
CAS Number	96087-37-5 Y
3D model (JSmol)	Interactive image
ChemSpider	2299671 Y
PubChem CID	3035428
UNII	53LXX17EV4 Y
InChI InChI=1S/C23H35N9O4S/c1-31(12-4-10-25-17-9-8-16(29-30-24)14-19(17)32(35)36)13-5-11-26-21(33)7-3-2-6-20-22-18(15-37-20)27-23(34)28-22/h8-9,14,18,20,22,25H,2-7,10-13,15H2,1H3,(H,26,33)(H2,27,28,34)/t18-,20?,22-/m0/s1 Y Key: BRLRJZRHRJEWJY-JERZPMBSSA-N Y InChI=1S/C23H35N9O4S/c1-31(12-4-10-25-17-9-8-16(29-30-24)14-19(17)32(35)36)13-5-11-26-21(33)7-3-2-6-20-22-18(15-37-20)27-23(34)28-22/h8-9,14,18,20,22,25H,2-7,10-13,15H2,1H3,(H,26,33)(H2,27,28,34)/t18-,20?,22-/m0/s1
SMILES O=C1N[C@@H]2C(SC[C@@H]2N1)CCCCC(=O)NCCCN(CCCNc3ccc(\N=[N+]=[N-])cc3[N+]([O-])=O)C
Properties
Chemical formula	C23H35N9O4S
Molar mass	533.65 g·mol−1
Appearance	Orange to red powder
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Tracking categories (test):

• SizeSet

Photobiotin is a derivative of biotin used as a biochemical tool. It is composed of a biotin group, a linker group, and a photoactivatable aryl azide group.

The photoactivatable group provides nonspecific labeling of proteins, DNA and RNA probes or other molecules. Biotinylation of DNA and RNA with photoactivatable biotin is easier and less expensive than enzymatic methods since the DNA and RNA does not degrade. Photobiotin is most effectively activated by light at 260-475 nm.

References

1. Billingsley, M. and J. Polli. “Preparation, characterization and biological properties of biotinylated derivatives of calmodulin.” Biochem J. 275 Pt 3(1991): 733–743
2. "EZ-Link Photoactivatable Biotin." Pierce Biotechnology, Inc. Rockford, IL: June, 2003.
3. "Components of Avidin-Biotin Technology: A Handbook." Pierce Biotechnology, Inc. Rockford, IL: June, 2003.
4. "Photobiotin acetate." Sigma-Aldrich, Co. 2006.
5. "Photoprobe biotin", Vector Laboratories, Inc., www.vectorlabs.com.
6. Hengsakul, Manchumas; Cass, Anthony E. G. (1996). "Protein Patterning with a Photoactivatable Derivative of Biotin". Bioconjugate Chemistry 7 (2): 249–254. doi:10.1021/bc960007z. PMID 8983347. 
7. Holden, Matthew A.; Cremer, Paul S. (2003). "Light Activated Patterning of Dye-Labeled Molecules on Surfaces". Journal of the American Chemical Society 125 (27): 8074–8075. doi:10.1021/ja035390e. PMID 12837056. 
8. Dontha, Narasaiah; Nowall, Wilbur B.; Kuhr, Werner G. (1997). "Generation of Biotin/Avidin/Enzyme Nanostructures with Maskless Photolithography". Analytical Chemistry 69 (14): 2619–2625. doi:10.1021/ac9702094. PMID 9230677.