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. 1974 Mar;1(3):479–489. doi: 10.1093/nar/1.3.479

Polynucleotides. XXIV1. Synthesis and properties of a dinucleoside monophosphate derived from uridine 6,2-cyclonucleoside2

Morio Ikehara 1, Toru Tezuka 1
PMCID: PMC344030  PMID: 10793680

Abstract

A dinucleoside monophosphate, 6,2′-anhydro-6-oxy-1-β-D-arabinofuranosyluracil-phosphoryl- (3′-5′)-6,2′-anhydro-6-oxy-1-β-D-arabinofuranosyluracil (I) was synthesized by the condensation reaction using DCC from 5′-monomethoxytrityl derivative(VII) and 3′-acetyl-5′-phosphate(X) of the monomer units. Yield was ca. 70%. UV of compound I showed no hypochromicity and its CD spectrum showed only a trough at 252 nm. No temperature dependency of ε and [Q] values was observed. These results suggested an unstacked random conformation for I.

Complex formation of I with cycloadenosine oligomer could not be detected under the experimental condition.

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Selected References

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  1. DONOHUE J., TRUEBLOOD K. N. Base pairing in DNA. J Mol Biol. 1960 Dec;2:363–371. doi: 10.1016/s0022-2836(60)80047-2. [DOI] [PubMed] [Google Scholar]
  2. Hampton A., Nichol A. W. Nucleotides. V. Purine ribonucleoside 2',3'-cyclic carbonates. Preparation and use for the synthesis of 5'-monosubstituted nucleosides. Biochemistry. 1966 Jun;5(6):2076–2082. doi: 10.1021/bi00870a040. [DOI] [PubMed] [Google Scholar]
  3. Ikehara M., Uesugi S., Yano J. Left-handed helical polynucleotides with D-sugar phosphodiester backbones. Nat New Biol. 1972 Nov 1;240(96):16–17. doi: 10.1038/newbio240016a0. [DOI] [PubMed] [Google Scholar]
  4. Otter B. A., Falco E. A., Fox J. J. Nucleosides. LII. Transformations of pyrimidine nucleosides in alkaline media. I. The conversion of 5-halogenoarabinosyluracils into imidazoline nucleosides. J Org Chem. 1968 Sep;33(9):3593–3600. doi: 10.1021/jo01273a053. [DOI] [PubMed] [Google Scholar]
  5. Tazawa I., Tazawa S., Stempel L. M., Ts'o P. O. L'adenylyl-(3'-5')-L-adenosine and L-adenylyl-(2'-5')-L-adenosine. Biochemistry. 1970 Sep 1;9(18):3499–3514. doi: 10.1021/bi00820a003. [DOI] [PubMed] [Google Scholar]
  6. Uesugi S., Yasumoto M., Ikehara M., Fang K. N., Ts'o P. O. Synthesis and properties of the dinucleoside monophosphate of adenine 8-thiocyclonucleoside. J Am Chem Soc. 1972 Jul 26;94(15):5480–5486. doi: 10.1021/ja00770a053. [DOI] [PubMed] [Google Scholar]

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