Abstract
alpha-phenyl cinnamoyl (alpha-PhCm) group has been found to be highly selective for exocylic amino function of all the three deoxynucleosides viz, 2'-deoxyadenosine, 2'-deoxyguanosine and 2'-deoxycytidine. The stereospecific nature of the group confers stability to the N-protected derivatives of 2'-deoxyadenosine and 2'-deoxyguanosine towards acids thereby minimising depurination. The easy preparation and introduction of the group, stability of the protected monomers, milder conditions for deprotection resulting in negligible side products during synthesis and above all hydrophobicity of the group are the additional advantages.
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Selected References
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- Büchi H., Khorana H. G. CV. Total synthesis of the structural gene for an alanine transfer ribonucleic acid from yeast. Chemical synthesis of an icosadeoxyribonucleotide corresponding to the nucleotide sequence 31 to 50. J Mol Biol. 1972 Dec 28;72(2):251–288. doi: 10.1016/0022-2836(72)90148-9. [DOI] [PubMed] [Google Scholar]
- Froehler B. C., Matteucci M. D. Dialkylformamidines: depurination resistant N6-protecting group for deoxyadenosine. Nucleic Acids Res. 1983 Nov 25;11(22):8031–8036. doi: 10.1093/nar/11.22.8031. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Garrett E. R., Mehta P. J. Solvolysis of adenine nucleosides. I. Effects of sugars and adenine substituents on acid solvolyses. J Am Chem Soc. 1972 Nov 29;94(24):8532–8541. doi: 10.1021/ja00779a040. [DOI] [PubMed] [Google Scholar]
- Jones R. A., Fritz H. J., Khorana H. G. Use of the lipophilic tert-butyldiphenylsilyl protecting group in synthesis and rapid separation of polynucleotides. Biochemistry. 1978 Apr 4;17(7):1268–1278. doi: 10.1021/bi00600a021. [DOI] [PubMed] [Google Scholar]
- KLENOW H., FREDERIKSEN S. Synthesis of 1-N-oxides of deoxyadenosine and deoxyadenosine monophosphate. Biochim Biophys Acta. 1961 Sep 16;52:384–386. doi: 10.1016/0006-3002(61)90691-6. [DOI] [PubMed] [Google Scholar]
- Kume A., Iwase R., Sekine M., Hata T. Cyclic diacyl groups for protection of the N6-amino group of deoxyadenosine in oligodeoxynucleotide synthesis. Nucleic Acids Res. 1984 Nov 26;12(22):8525–8538. doi: 10.1093/nar/12.22.8525. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Mishra R. K., Misra K. Improved synthesis of oligodeoxyribonucleotide using 3-methoxy-4-phenoxybenzoyl group for amino protection. Nucleic Acids Res. 1986 Aug 11;14(15):6197–6213. doi: 10.1093/nar/14.15.6197. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Stawinski J., Hozumi T., Narang S. A., Bahl C. P., Wu R. Arylsulfonyltetrazoles, new coupling reagents and further improvements in the triester method for the synthesis of deoxyribooligonucleotides. Nucleic Acids Res. 1977 Feb;4(2):353–371. doi: 10.1093/nar/4.2.353. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Tanaka T., Letsinger R. L. Syringe method for stepwise chemical synthesis of oligonucleotides. Nucleic Acids Res. 1982 May 25;10(10):3249–3260. doi: 10.1093/nar/10.10.3249. [DOI] [PMC free article] [PubMed] [Google Scholar]
