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Photobiotin

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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
3D model (JSmol)
ChemSpider
  • 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 checkY
    Key: BRLRJZRHRJEWJY-JERZPMBSSA-N checkY
  • 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
  • O=C1N[C@@H]2C(SC[C@@H]2N1)CCCCC(=O)NCCCN(CCCNc3ccc(\N=[N+]=[N-])cc3[N+]([O-])=O)C
Properties
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).
checkY verify (what is checkY☒N ?)

Photobiotin is a 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

  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.
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