2′-Deoxy-5-methylisocytidine

Seela, Frank; He, Yang; Reuter, Hans; Heithoff, Eva-Maria

doi:10.1107/s0108270100006247

Cited by 5 publications

(10 citation statements)

References 19 publications

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“…According to Steiner (2002), for bifurcated hydrogen bonds with distinctly different hydrogen-acceptor separations, the shorter interaction is defined as the major component and the longer one as the minor. A similar intramolecular bifurcated hydrogenbonding pattern was also observed in the crystal structures of 2-chloro-2 0 -deoxyadenosine, (IV) (Worthington et al, 1995), and 2 0 -deoxy-5-methylisocytidine, (V) (Seela et al, 2000). The minor component utilizes atom O4 0 as acceptor, with N6Á Á ÁO4 0 = 3.1676 (15) Å and N6-H6BÁ Á Á O4 0 = 143 .…”

Section: Commentsupporting

confidence: 69%

7-Amino-1-(2-deoxy-β-erythro-pentofuranosyl)-1H-1,2,3-triazolo[4,5-d]pyrimidine: an 8-azaadenine nucleoside with the nucleobase in asynconformation

Jiang

Budow

et al. 2010

Acta Crystallogr C

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The title compound, C(9)H(12)N(6)O(3), shows a syn-glycosylic bond orientation [χ = 64.17 (16)°]. The 2'-deoxyfuranosyl moiety exhibits an unusual C1'-exo-O4'-endo ((1)T(0); S-type) sugar pucker, with P = 111.5 (1)° and τ(m) = 40.3 (1)°. The conformation at the exocyclic C4'-C5' bond is +sc (gauche), with γ = 64.4 (1)°. The two-dimensional hydrogen-bonded network is built from intermolecular N-H...O and O-H...N hydrogen bonds. An intramolecular bifurcated hydrogen bond, with an amino N-H group as hydrogen-bond donor and the ring and hydroxymethyl O atoms of the sugar moiety as acceptors, constrains the overall conformation of the nucleoside.

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Section: Commentsupporting

confidence: 69%

7-Amino-1-(2-deoxy-β-erythro-pentofuranosyl)-1H-1,2,3-triazolo[4,5-d]pyrimidine: an 8-azaadenine nucleoside with the nucleobase in asynconformation

Jiang

Budow

et al. 2010

Acta Crystallogr C

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“…Isocytosine can exist in various tautomeric forms, however, the experimental and theoretical data are consistent with the fact that 1-substituted iC adopts the 2-amino-4-oxo form ( Figure 1A) in environments of intermediate to high polarity ( [31] and references cited therein). 2h-Deoxy-5-methylisocytidine exists in the 2-amino-4-oxo form in the crystalline state [34].…”

Section: Discussionmentioning

confidence: 99%

Neighbouring bases in template influence base-pairing of isoguanine

Maciejewska

Lichota

Kuśmierek

2003

Biochemical Journal

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Assuming that the efficiency of the incorporation of 5-methyl-2h-deoxyisocytosine-5h triphosphate (dMiCTP) and dTTP opposite isoguanine (iG) is a measure of the proportion of the keto and enol tautomers of iG in the Thermus aquaticus DNA polymerase active centre, we studied the influence of temperature and iGneighbouring bases in the template on base-pairing of iG. On the basis of experiments with four sequences (3h-TXT-5h, 3h-GXG-5h, 3h-CXC-5h, 3h-CXT-5h, where X l iG) at 37, 50, 65 and 80 mC, we found that 3h-neighbours decrease the fraction of the keto tautomer in the order C G T, whereas temperature apparently does not influence the tautomeric equilibrium of iG. The variability of the ratio of incorporation of dMiCTP versus dTTP (5-20) primarily reflects the variability of K m values, since

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“…We assume that our experimental observation that D-pr( Me isoC 8 ) pairs with L-pr(G 8 ) (heterochiral case) but not with D-pr(isoG 8 ) (isochiral case) can be interpreted accordingly: the main structural difference between the isocytosine and the canonical nucleobases of relevance for the interpretation of this observation is the 2-amino group replacing the O-atom. When incorporated into a ribopyranosyl nucleotide, the protons of the isocytosine amino group and the anomeric proton sustain a steric strain, which can be relieved by a change of the nucleosidic torsion angle c, presumably specific for the isocytosine moiety in direction and/or extent in relation to the other canonical pyrimidine nucleobases (see [15] for the furanosebased nucleotide). In Fig.…”

Section: Results -Synthesis Of Thementioning

confidence: 99%

The 5‐Methylisocytosine β‐D‐Ribopyranosyl (4′ → 2′)‐Oligonucleotide

Bats

Miculka

2006

Helvetica Chimica Acta

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In the context of Eschenmoser's work on pyranosyl-RNA ('p-RNA'), we investigated the synthesis and base-pairing properties of the 5-methylisocytidine derivative. The previously determined clear-cut restrictions of base-pairing modes of p-RNA had led to the expectation that a 5-methylisocytosine b-D-ribopyranosyl (= D-pr( Me isoC)) based (4' ! 2')-oligonucleotide would pair inter alia with D-pr(isoG) and L-pr(G) based oligonucleotides (D-pr and L-pr = pyranose form of D-and L-ribose, resp.). Remarkably, we could not observe pairing with the D-pr(isoG) oligonucleotide but only with the L-pr(G) oligonucleotide. Our interpretation concludes that this -at first hand surprising -observation is caused by a change in the nucleosidic torsion angle specific for isoC.

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2′-Deoxy-5-methylisocytidine

Cited by 5 publications

References 19 publications

7-Amino-1-(2-deoxy-β-erythro-pentofuranosyl)-1H-1,2,3-triazolo[4,5-d]pyrimidine: an 8-azaadenine nucleoside with the nucleobase in asynconformation

7-Amino-1-(2-deoxy-β-erythro-pentofuranosyl)-1H-1,2,3-triazolo[4,5-d]pyrimidine: an 8-azaadenine nucleoside with the nucleobase in asynconformation

Neighbouring bases in template influence base-pairing of isoguanine

The 5‐Methylisocytosine β‐D‐Ribopyranosyl (4′ → 2′)‐Oligonucleotide

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