Abstract
A pentadecanucleotide was prepared from 1-alpha-arabinofuranosylthymine. This novel oligonucleotide was found to hybridize to oligodeoxyadenylate, although not a s strongly as pentadecathymidylate. It formed duplex hybrids with both DNA and RNA complements, and triplex structures with a duplex containing a (dT)15-(dA)15 tract within a more complex strand. The Tm of the duplex with polyadenylate was almost the same as that of (dT)15 and polyadenylate, while its Tm with (dA)15 was substantially lower than that of the natural counterpart. A selective benzoylation of the 2'-O of a 5'-blocked alpha-ara-thymine was developed to greatly simplify the preparation of suitable blocked material for use in preparation of oligonucleotides on the automated DNA synthesizer.
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Selected References
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- Beardsley G. P., Mikita T., Klaus M. M., Nussbaum A. L. Chemical synthesis of DNA oligomers containing cytosine arabinoside. Nucleic Acids Res. 1988 Oct 11;16(19):9165–9176. doi: 10.1093/nar/16.19.9165. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Cazenave C., Chevrier M., Nguyen T. T., Hélène C. Rate of degradation of [alpha]- and [beta]-oligodeoxynucleotides in Xenopus oocytes. Implications for anti-messenger strategies. Nucleic Acids Res. 1987 Dec 23;15(24):10507–10521. doi: 10.1093/nar/15.24.10507. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Durand M., Maurizot J. C., Thuong N. T., Helene C. Circular dichroism studies of an oligo-alpha-thymidylate and of its interactions with complementary sequences. Nucleic Acids Res. 1988 Jun 10;16(11):5039–5053. doi: 10.1093/nar/16.11.5039. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Gagnor C., Bertrand J. R., Thenet S., Lemaître M., Morvan F., Rayner B., Malvy C., Lebleu B., Imbach J. L., Paoletti C. alpha-DNA. VI: Comparative study of alpha- and beta-anomeric oligodeoxyribonucleotides in hybridization to mRNA and in cell free translation inhibition. Nucleic Acids Res. 1987 Dec 23;15(24):10419–10436. doi: 10.1093/nar/15.24.10419. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Gautier C., Morvan F., Rayner B., Huynh-Dinh T., Igolen J., Imbach J. L., Paoletti C., Paoletti J. Alpha-DNA. IV: Alpha-anomeric and beta-anomeric tetrathymidylates covalently linked to intercalating oxazolopyridocarbazole. Synthesis, physicochemical properties and poly (rA) binding. Nucleic Acids Res. 1987 Aug 25;15(16):6625–6641. doi: 10.1093/nar/15.16.6625. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Le Doan T., Perrouault L., Praseuth D., Habhoub N., Decout J. L., Thuong N. T., Lhomme J., Hélène C. Sequence-specific recognition, photocrosslinking and cleavage of the DNA double helix by an oligo-[alpha]-thymidylate covalently linked to an azidoproflavine derivative. Nucleic Acids Res. 1987 Oct 12;15(19):7749–7760. doi: 10.1093/nar/15.19.7749. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Morvan F., Rayner B., Imbach J. L., Lee M., Hartley J. A., Chang D. K., Lown J. W. alpha-DNA-V. Parallel annealing, handedness and conformation of the duplex of the unnatural alpha-hexadeoxyribonucleotide alpha-[d(CpApTpGpCpG)] with its beta-complement beta-[d(GpTpApCpGpC)] deduced from high field 1H-NMR. Nucleic Acids Res. 1987 Sep 11;15(17):7027–7044. doi: 10.1093/nar/15.17.7027. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Nishimura T., Shimizu B. Studies on synthetic nucleosides V. Anomeric pyrimidine nucleosides of D-arabinose and D-lyxose. Chem Pharm Bull (Tokyo) 1965 Jul;13(7):803–810. doi: 10.1248/cpb.13.803. [DOI] [PubMed] [Google Scholar]
- Paoletti J., Bazile D., Morvan F., Imbach J. L., Paoletti C. Alpha-DNA VIII: thermodynamic parameters of complexes formed between the oligo-alpha-deoxynucleotides: alpha-d(GGAAGG) and alpha-d(CCTTCC) and their complementary oligo-beta-deoxynucleotides: beta-d(CCTTCC) and beta-d(GGAAGG) are different. Nucleic Acids Res. 1989 Apr 11;17(7):2693–2704. doi: 10.1093/nar/17.7.2693. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Praseuth D., Perrouault L., Le Doan T., Chassignol M., Thuong N., Hélène C. Sequence-specific binding and photocrosslinking of alpha and beta oligodeoxynucleotides to the major groove of DNA via triple-helix formation. Proc Natl Acad Sci U S A. 1988 Mar;85(5):1349–1353. doi: 10.1073/pnas.85.5.1349. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Shea R. G., Ng P., Bischofberger N. Thermal denaturation profiles and gel mobility shift analysis of oligodeoxynucleotide triplexes. Nucleic Acids Res. 1990 Aug 25;18(16):4859–4866. doi: 10.1093/nar/18.16.4859. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Sinha N. D., Biernat J., McManus J., Köster H. Polymer support oligonucleotide synthesis XVIII: use of beta-cyanoethyl-N,N-dialkylamino-/N-morpholino phosphoramidite of deoxynucleosides for the synthesis of DNA fragments simplifying deprotection and isolation of the final product. Nucleic Acids Res. 1984 Jun 11;12(11):4539–4557. doi: 10.1093/nar/12.11.4539. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Sun J. S., Asseline U., Rouzaud D., Montenay-Garestier T., Nguyen T. T., Hélène C. Oligo-[alpha]-deoxynucleotides covalently linked to an intercalating agent. Double helices with parallel strands are formed with complementary oligo-[beta]-deoxynucleotides. Nucleic Acids Res. 1987 Aug 11;15(15):6149–6158. doi: 10.1093/nar/15.15.6149. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Thuong N. T., Asseline U., Roig V., Takasugi M., Hélène C. Oligo(alpha-deoxynucleotide)s covalently linked to intercalating agents: differential binding to ribo- and deoxyribopolynucleotides and stability towards nuclease digestion. Proc Natl Acad Sci U S A. 1987 Aug;84(15):5129–5133. doi: 10.1073/pnas.84.15.5129. [DOI] [PMC free article] [PubMed] [Google Scholar]