Photobiotin

Photobiotin

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
PubChem	3035428
ChemSpider	2299671^Y
Jmol-3D images	Image 1
SMILES O=C1N[C@@H]2C(SC[C@@H]2N1)CCCCC(=O)NCCCN(CCCNc3ccc(\N=[N+]=[N-])cc3[N+]([O-])=O)C
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=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
Properties
Molecular formula	C₂₃H₃₅N₉O₄S
Molar mass	533.65 g mol⁻¹
Appearance	Orange to red powder
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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

Billingsley, M. and J. Polli. “Preparation, characterization and biological properties of biotinylated derivatives of calmodulin.” Biochem J. 275 Pt 3(1991): 733–743
"EZ-Link Photoactivatable Biotin." Pierce Biotechnology, Inc. Rockford, IL: June, 2003.
"Components of Avidin-Biotin Technology: A Handbook." Pierce Biotechnology, Inc. Rockford, IL: June, 2003.
"Photobiotin acetate." Sigma-Aldrich, Co. 2006.
"Photoprobe biotin", Vector Laboratories, Inc., www.vectorlabs.com.
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.
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.
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.