Abstract
Flavin 1,N6-ethenoadenine dinucleotide (εFAD) was prepared by the action of chloroacetaldehyde on flavin adenine dinucleotide. This compound, which has two potential fluorophores, ε-adenine and isoalloxazine, shows extremely efficient energy transfer from the former to the latter. The fluorescences of both moieties are greatly diminished in the intact molecule. Determination of the fluorescence yields and lifetimes leads to the conclusion that at 20° in neutral aqueous solution εFAD exists mainly (90%) as an internally complexed or stacked form.
Keywords: FAD; 1,N6-ethenoadenine derivative; fluorescence emission; coenzyme analogue; energy transfer
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Selected References
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- Barrio J. R., Secrist J. A., 3rd, Leonard N. J. A fluorescent analog of nicotinamide adenine dinucleotide. Proc Natl Acad Sci U S A. 1972 Aug;69(8):2039–2042. doi: 10.1073/pnas.69.8.2039. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Barrio J. R., Secrist J. A., 3rd, Leonard N. J. Fluorescent adenosine and cytidine derivatives. Biochem Biophys Res Commun. 1972 Jan 31;46(2):597–604. doi: 10.1016/s0006-291x(72)80181-5. [DOI] [PubMed] [Google Scholar]
- Harvey R. A., Damle S. A fluorescent modification of flavin adenine dinucleotide. FEBS Lett. 1972 Oct 1;26(1):341–343. doi: 10.1016/0014-5793(72)80607-0. [DOI] [PubMed] [Google Scholar]
- Leonard N. J., Barrio J. R., Secrist J. A., 3rd A spray reagent for adenine-containing residues: detection by fluorescence. Biochim Biophys Acta. 1972 May 29;269(3):531–532. doi: 10.1016/0005-2787(72)90145-1. [DOI] [PubMed] [Google Scholar]
- MASSEY V., SWOBODA B. E. THE FLAVIN COMPOSITION OF PIG HEART MUSCLE PREPARATIONS. Biochem Z. 1963;338:474–484. [PubMed] [Google Scholar]
- Secrist J. A., 3rd, Barrio J. R., Leonard N. J. A fluorescent modification of adenosine triphosphate with activity in enzyme systems: 1,N 6 -ethenoadenosine triphosphate. Science. 1972 Feb 11;175(4022):646–647. doi: 10.1126/science.175.4022.646. [DOI] [PubMed] [Google Scholar]
- Secrist J. A., 3rd, Barrio J. R., Leonard N. J., Villar-Palasi C., Gilman A. G. Fluorescent modification of adenosine 3',5'-monophosphate: spectroscopic properties and activity in enzyme systems. Science. 1972 Jul 21;177(4045):279–280. doi: 10.1126/science.177.4045.279. [DOI] [PubMed] [Google Scholar]
- Secrist J. A., 3rd, Barrio J. R., Leonard N. J., Weber G. Fluorescent modification of adenosine-containing coenzymes. Biological activities and spectroscopic properties. Biochemistry. 1972 Sep 12;11(19):3499–3506. doi: 10.1021/bi00769a001. [DOI] [PubMed] [Google Scholar]