Photobiotin

Last updated
Photobiotin
Photobiotin.svg
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
PubChem CID
UNII
  • 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 Yes check.svgY
    Key: BRLRJZRHRJEWJY-JERZPMBSSA-N Yes check.svgY
  • 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
AppearanceOrange to red powder
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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.
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