Synthesis of Some Substituted Nucleoside Analogs

Seita, Toru; Kinoshita, Masayoshi; Imoto, Minoru

doi:10.1246/bcsj.46.1572

Cited by 17 publications

(5 citation statements)

References 4 publications

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“…The mixture was then filtered through Celite and applied to an Amberlite IR 4 B (acetate)-column (300 ml). The tV-absorbing material was eluted with wate, (3 ml/mi, checked by the Uvicord apparatus), evaporated and applied on a Duwex 50 X 8 (100-200 mesh, hI-form) colum (300 l). Again, the neutral UV-absorbing fraction was eluted with water under the same conditions and the eluate evaporated to dryness and-crystallized from ethanol.…”

Section: D_o_z2mentioning

confidence: 99%

Aliphatic analogues of nucleotides: synthesis and affinity towards nucleases

Holý

Ivanova

1974

Nucl Acids Res

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DL-1-(2,3-Dihydroxypropyl)thymine was prepared by Hilbert-Johnson reaction of 2,4-dinethoxy-5-methylpyrimidine with allyl bromide followed by the osmium tetroxide catalyzed hydroxylation of the l-allyl-4-methoxy-5-methylpyrimidin-2-one obtained as an intermediate. The D-glycero enantiomer, R-1-(2,3-dihydroxypropyl)thymine and the corresponding 1-substituted uracil derivative were prepared from 3-O-p-toluenesulfonyl-1, 2-O-isopropylidene-D-glycerine and sodium salt of 4-methoxy-5-methylpyrimidin-2-one or 4-methoxypyrimidin-2-one followed by treatment with hydrogen chloride in ethanol. The phosphorylation of the above 2,3-dihydroxypropyl derivatives with phosphoryl chloride in triethyl phosphate afforded the corresponding 3-phosphates which were transformed into the 2',3'-cyclic phosphates by the condensation with N,N'-dicyclohexylcarbodiimide. The latter compounds of the D-glycero configuration are split by some microbial RNases to the 3-phosphates.

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Section: D_o_z2mentioning

confidence: 99%

Aliphatic analogues of nucleotides: synthesis and affinity towards nucleases

Holý

Ivanova

1974

Nucl Acids Res

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Section: ■ Introductionmentioning

confidence: 99%

“…Because of the presence of the single stereogenic center, the given GNA nucleoside can exist as either an S or an R enantiomer. The chemistry of GNA was studied in the 1970s, when Ueda and Imoto , first reported the synthesis of the racemic GNA nucleosides and their oligomerization products . Since then, interest in the GNA synthesis has continued. − Recently, Meggers and co-workers conducted extensive research on GNA chemistry ,− and crystallography. , They determined X-ray crystal structures of Br-containing and Cu(II)-containing self-complementary right-handed ( S )-GNA duplexes. − The X-ray diffraction studies showed that the copper(II)-containing ( S )-GNA duplex forms an elongated M-type helix, while the 5-bromocytosine-bearing duplex forms a more condensed N-type helix .…”

Section: Introductionmentioning

confidence: 99%

Redox-Active Glycol Nucleic Acid (GNA) Components: Synthesis and Properties of the Ferrocenyl-GNA Nucleoside, Phosphoramidite, and Semicanonical Dinucleoside Phosphate

et al. 2020

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Ferrocenylated glycol nucleic acid (Fc-GNA) components are rarely studied in the field of xeno nucleic acid (XNA) chemistry. As an attempt to contribute to XNA chemistry, in the present article we report a seven-step synthesis of the first semicanonical dinucleoside containing the Fc-GNA nucleoside linked to the adenosine nucleoside with a phosphodiester bond. First, the nucleoside-bearing ethynylferrocenyl moiety in the C5 position of the uracil nucleobase was obtained. In the following steps, the nucleoside was transformed into the phosphoramidite intermediate that in turn was reacted with N 6-benzoyl-2′,3′-O-isopropylideneadenosine to afford the target dinucleoside phosphate with 47% yield. The newly obtained Fc-GNA nucleoside is redox-active, and on the basis of this property (function), it belongs to a new class of functional GNA (fun-GNA) nucleosides. The electrochemistry of the Fc-GNA nucleoside, dinucleoside phosphate, and ferrocenyl furanopyrimidone nucleoside that was obtained as an undesired byproduct of Fc-GNA nucleoside synthesis was investigated by cyclic voltammetry (CV). The CV result showed the presence of a one-electron ferrocenyl-centered redox wave in each case. The half-wave potentials of the Fc-GNA nucleoside and dinucleoside phosphate were 89 and 99 mV, respectively, against the FcH/FcH+ couple. Finally, the activity of the newly obtained Fc-GNA components was studied against the nontumorigenic mouse L929 and human cervix adenocarcinoma HeLa cells. The synthesized compounds showed no cytotoxic activity against the tested cell lines.

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“…[10][11][12] The synthesis of 2,3-dihydroxypropyl derivatives of nucleobases (glycol nucleosides/nucleotides) has been reported from various starting materials, [12][13][14][15][16][17][18][19][20][21][22] most notably, from isopropylideneglycerol by tosylation of the hydroxyl group followed by nucleophilic substitution with a nucleobase or nucleobase derivative, [12][13][14][15][16][17][18] or in a different strategy, by direct ring-opening of glycidol with nucleobases or nucleobase derivatives. [19][20][21] We were attracted by the shorter and more straightforward approach starting with 'spring-loaded' glycidol. [19][20][21] The presented synthetic schemes are related to a published communication by Acevedo and Andrews, in which no experimental details were provided.…”

mentioning

confidence: 99%

“…[19][20][21] We were attracted by the shorter and more straightforward approach starting with 'spring-loaded' glycidol. [19][20][21] The presented synthetic schemes are related to a published communication by Acevedo and Andrews, in which no experimental details were provided. 21 The glycol nucleosides are accessible starting from the commercially available enantiomerically pure (R)-(+)and (S)-(-)-glycidols.…”

mentioning

confidence: 99%

Synthesis of Glycol Nucleic Acids

Zhang¹,

Peritz²,

Carroll³

et al. 2006

Synthesis

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Starting from glycidol, the synthesis of dimethoxytritylated glycol nucleoside phosphoramidites of adenine (A), thymine (T), uracil (U), guanine (G), and cytosine (C) is reported. These phosphoramidites are the building blocks for the automated solid phase synthesis of glycol nucleic acids (GNA) oligonucleotides and it is demonstrated that derived GNA duplexes with completely acyclic backbones considerably exceed the thermal stabilities of analogous DNA duplexes.

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Synthesis of Some Substituted Nucleoside Analogs

Cited by 17 publications

References 4 publications

Aliphatic analogues of nucleotides: synthesis and affinity towards nucleases

Aliphatic analogues of nucleotides: synthesis and affinity towards nucleases

Redox-Active Glycol Nucleic Acid (GNA) Components: Synthesis and Properties of the Ferrocenyl-GNA Nucleoside, Phosphoramidite, and Semicanonical Dinucleoside Phosphate

Synthesis of Glycol Nucleic Acids

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