Abstract
Interaction of cytidine 5'-phosphate with chloroacetone or p-tosyloxyacetone leads to 2-methyl-5,6-dihydro-5-oxo-6-(5-0-phospho-beta-D-ribofuranosyl)-imidazo/1,2-c/pyrimidine (2-methylethenocytidine 5'-phosphate) whereas analogous reaction with phenacyl bromide produces similar 2-phenyl-derivative. The bicyclic nucleotides obtained showed significant UV absorption at long wavelength where common nucleotides and proteins exhibited no absorption. These derivatives are highly fluorescent when heterocyclic ring is protonated. The absorption and fluorescent properties of the substituted ethenocytidine 5'-phosphoate derivatives seem to be suitable for their use as fluorescent probes or labels in biochemical studies.
Full text
PDF








Selected References
These references are in PubMed. This may not be the complete list of references from this article.
- Barrio J. R., Dammann L. G., Kirkegaard L. H., Switzer R. L., Leonard N. J. Enzymatic activity and - 32 P labeling of fluorescent derivatives of cytidine triphosphate and adenosine triphosphate. J Am Chem Soc. 1973 Feb 7;95(3):961–962. doi: 10.1021/ja00784a075. [DOI] [PubMed] [Google Scholar]
- Barrio J. R., Leonard N. J. Specific and fluorescent modifications of cytidine. J Am Chem Soc. 1973 Feb 21;95(4):1323–1328. doi: 10.1021/ja00785a051. [DOI] [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]
- Greenfield J. C., Leonard N. J., Gumport R. I. Nicotinamide 3,N4-ethenocytosine dinucleotide, an analog of nicotinamide adenine dinucleotide. Synthesis and enzyme studies. Biochemistry. 1975 Feb 25;14(4):698–706. doi: 10.1021/bi00675a009. [DOI] [PubMed] [Google Scholar]
- HANES C. S., ISHERWOOD F. A. Separation of the phosphoric esters on the filter paper chromatogram. Nature. 1949 Dec 31;164(4183):1107-12, illust. doi: 10.1038/1641107a0. [DOI] [PubMed] [Google Scholar]
- Kochetkov N. K., Shibaev V. N., Kost A. A. Vzaimodeistvie komponentov DNK s khloratsetal'degidom. Dokl Akad Nauk SSSR. 1973 Dec 21;213(6):1327–1330. [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]
- Tolman G. L., Barrio J. R., Leonard N. J. Chloroacetaldehyde-modified dinucleoside phosphates. Dynamic fluorescence quenching and quenching due to intramolecular complexation. Biochemistry. 1974 Nov 19;13(24):4869–4878. doi: 10.1021/bi00721a001. [DOI] [PubMed] [Google Scholar]
