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Left-handed Helical Polynucleotides with D-Sugar Phosphodiester Backbones

Nature New Biology volume 240, pages 16–17 (1972)Cite this article

Abstract

Naturally occurring polynucleotides have right-handed helical confrontations in the solid state1 and in solution2. Poly(dI-dC)poly(dI-dC) was found to form a left-handed helix in spite of the D-sugar backbone. Also, L-adenylyl-(3′–5′)-L-adenosine synthesized by Tazawa et al4. takes up the left-handed stacked conformation. We had synthesized a dinucleoside monophosphate, 8,2′-anhydro-8-mercapto-9-β-D-arabinofuranosyladenine phosphoryl-(3′–5′)-8,2′-anhydro-8-mercapto-9-β-D-arabinofuranosyladenine (AspAs) (molecular structure Ia; see also ref. 5), and this compound has a left-handed stacked conformation. The two bases in Ia, having the D-sugar backbone, stacked along the left-handed helical axis; these bases are fixed at ϕCN = −108° (syn-anti region) by the anhydro linkages.

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References

  1. Davies, D. R., Ann. Rev. Biochem., 36, 321 (1967).

    Article  CAS  Google Scholar 

  2. Cantor, C. R., and Tinoco, I., jun., J. Mol. Biol., 13, 65 (1965).

    Article  CAS  Google Scholar 

  3. Mitsui, Y., Langridge, R., Shortle, B. E., Cantor, C. R., Grant, R. C., Kodama, M., and Wells, R. D., Nature, 228, 1166 (1970).

    Article  CAS  Google Scholar 

  4. Tazawa, I., Tazawa, S., Stempel, L. M., and Ts'o, P. O. P., Biochemistry, 9, 3499 (1970).

    Article  CAS  Google Scholar 

  5. Ikehara, M., Uesugi, S., and Yasumoto, M., J. Amer. Chem. Soc., 92, 4735 (1970).

    Article  CAS  Google Scholar 

  6. Ikehara, M., and Kaneko, M., Chem. Pharmac. Bull., 18, 2401 (1970).

    Article  CAS  Google Scholar 

  7. Tinoco, I., jun., Woody, R. W., and Bradley, D. F., J. Chem. Phys., 38, 1317 (1963).

    Article  CAS  Google Scholar 

  8. Ts'o, P. O. P., Kondo, N. S., Schweizer, M. P., and Hollis, D. P., Biochemistry, 8, 997 (1969).

    Article  CAS  Google Scholar 

  9. Ikehara, M., and Uesugi, S., Tetrahed. Lett., 713 (1970).

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Authors and Affiliations

  1. Faculty of Pharmaceutical Sciences, Osaka University, Osaka

    MORIO IKEHARA, SEIICHI UESUGI & JUNICHI YANO

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  1. MORIO IKEHARA
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  2. SEIICHI UESUGI
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  3. JUNICHI YANO
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IKEHARA, M., UESUGI, S. & YANO, J. Left-handed Helical Polynucleotides with D-Sugar Phosphodiester Backbones. Nature New Biology 240, 16–17 (1972). https://doi.org/10.1038/newbio240016a0

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