Abstract
2-Thiouridine, 4-thiouridine and the corresponding thiouracils were quantitatively modified with aqueous chloroacetaldehyde /37 degrees C, pH 3.0--6.5/. The rate-pH dependence found for the disappearance of the substrates suggested initial S-alkylation. The unstable S-acetaldehydyl intermediates were not detected due to their further rapid transformations. The following possibilities of such transformations are discussed: 1. intramolecular addition of the endocyclic nitrogen atom to the aldehyde carbonyl group to form the "hydroxyethano" bridged compounds, 2. hydrolysis to the corresponding "oxo" analogues of the substrates, 3. hydrolysis of the N-glycoside bond. The structures of new compounds formed in these reactions were assigned on the basis of their FD-MS, UV, IR and PMR spectra. The reaction rates were similar to those found for modification of adenosine and cytidine with chloroacetaldehyde.
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., 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]
- 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]
- Sattsangi P. D., Leonard N. J., Frihart C. R. 1,N2-ethenoguanine and N2,3-ethenoguanine. Synthesis and comparison of the electronic spectral properties of these linear and angular triheterocycles related to the Y bases. J Org Chem. 1977 Sep 30;42(20):3292–3296. doi: 10.1021/jo00440a020. [DOI] [PubMed] [Google Scholar]
- Schulman L. H., Pelka H. Location of accessible bases in Escherichia coli formylmethionine transfer RNA as determined by chemical modification. Biochemistry. 1976 Dec 28;15(26):5769–5775. doi: 10.1021/bi00671a013. [DOI] [PubMed] [Google Scholar]
- Schwartz I., Gordon E., Ofengand J. Photoaffinity labeling of the ribosomal A site with S-(p-azidophenacyl)valyl-tRNA. Biochemistry. 1975 Jul;14(13):2907–2914. doi: 10.1021/bi00684a018. [DOI] [PubMed] [Google Scholar]
- Singer B., Kröger M., Carrano M. O2- and O4-alkyl pyrimidine nucleosides: stability of the glycosyl bond and of the alkyl group as a function of pH. Biochemistry. 1978 Apr 4;17(7):1246–1250. doi: 10.1021/bi00600a018. [DOI] [PubMed] [Google Scholar]