Base-Modified Nucleosides: Etheno Derivatives
نویسندگان
چکیده
This review presents synthesis and chemistry of nucleoside analogs, possessing an additional fused, heterocyclic ring of the "etheno" type, such as 1,N(6)-ethenoadenosine, 1,N(4)-ethenocytidine, 1,N(2)-ethenoguanosine, and other related derivatives. Formation of ethenonucleosides, in the presence of α-halocarbonyl reagents and their mechanism, stability, and degradation, reactions of substitution and transglycosylation, as well as their application in the nucleoside synthesis, have been described. Some of the discussed compounds may be applied as chemotherapeutic agents in antiviral and anticancer treatment, acting as pro-nucleosides of already known, biologically active nucleoside analogs.
منابع مشابه
Miscodes In Vitro Using Mammalian Polymerases †
8-(hydroxymethyl)-3,N-etheno-dC (8-HM-εC), is a mutagen and animal carcinogen resulting from the reaction of dC with glycidaldehyde. It was synthesized and its phosphoramidite was incorporated site-specifically into a defined 25-mer oligonucleotide. In this study the mutagenic potential of this compound was investigated in an in vitro primer-template extension assay using four mammalian DNA pol...
متن کاملMismatch discrimination of base-modified nucleic acids and their constituents: non-Watson-Crick base pairing induced by tautomerization.
The effect of tautomerism on the mismatch discrimination was studied on 7-deazapurine and 8-aza-7-deazapurine analogues of isoguanosine. 7-Halogenated 7-deaza-2'-deoxyisoguanosines show better base pair discrimination than 2'-deoxyisoguanosine due to the more favored keto tautomer formation. 8-Aza-7-deazaisoguanosine and its 7-halogeno derivatives also show higher keto tautomer population than ...
متن کاملPyrazolo[3,4-d][1,2,3]triazine DNA: synthesis and base pairing of 7-deaza-2,8-diaza-2'-deoxyadenosine.
7-deaza-2,8-diaza-2'-deoxyadenosine (4) was synthesized from 8-aza-7-deaza-2'-deoxyadenosine (1) via the 1,N(6)-etheno derivative 5. Ring opening with sodium hydroxide followed by ring closure in the presence of sodium nitrite formed the tricyclic intermediate 5 from which the transiently introduced "etheno" moiety was removed with NBS. Compound 4 was converted to the phosphoramidite 11, which ...
متن کاملPyrrolo[2,3‐d]pyrimidine (7‐deazapurine) as a privileged scaffold in design of antitumor and antiviral nucleosides
7-Deazapurine (pyrrolo[2,3-d]pyrimidine) nucleosides are important analogues of biogenic purine nucleosides with diverse biological activities. Replacement of the N7 atom with a carbon atom makes the five-membered ring more electron rich and brings a possibility of attaching additional substituents at the C7 position. This often leads to derivatives with increased base-pairing in DNA or RNA or ...
متن کاملStructural studies of malonaldehyde–glyoxal and malonaldehyde–methylglyoxal etheno adducts of adenine nucleosides based on spectroscopic methods and DFT-GIAO calculations†
Etheno adducts are formed in the reactions of DNA bases with chloroacetaldehyde, with lipid peroxidation products, and also with metabolites of vinyl chloride and furan. The presence of such modifications in the genetic material may lead to errors in replication with consequences of mutations and even carcinogenesis. For an understanding of the biological significance of etheno adducts it is im...
متن کامل