Synthesis and Restricted Conformation of 3′,5′-<i>O</i>-(Di-<i>t</i>-butylsilanediyl)ribonucleosides

Furusawa, Kazuya; Ueno, Katsuhiko; Katsura, Takeshi

doi:10.1246/cl.1990.97

Cited by 61 publications

(35 citation statements)

References 16 publications

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“…To 2- N -isobutyryl-2′- O - tert- butyldimethylsilyl-5′- O -(4,4′-dimethoxytrityl)-guanosine37,38 (3.85 g, 5.0 mmol) dissolved in 15 mL of dry pyridine was added diphenyl phosphite (1.9 mL, 10 mmol, 2 eq). After 15 min at room temperature the reaction mixture was poured into saturated NaHCO 3 and extracted with CH 2 Cl 2 (3 × 50 mL).…”

Section: Methodsmentioning

confidence: 99%

Thiophosphate Analogs of c-di-GMP: Impact on Polymorphism

Zhao

Veliath

Kim

et al. 2009

Nucleosides, Nucleotides & Nucleic Acids

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Seven phosphorothioate analogs of c-di-GMP (all diastereomers of mono-, di-, and trithiophosphates) were prepared to assess the impact of the thioate substitutions on c-di-GMP polymorphism using 1D 1 H and 31 P NMR, along with 2D NOESY and DOSY, for both the Na + and K + salts. The K + salts display more extensive higher order complex formation than the Na + salts, resulting primarily in octamolecular complexes with K + , but tetramolecular complexes with Na + . Further, the presence of one or two [S P ] sulfurs specifically stabilizes anti complexes and/or destabilizes syn complexes, while the presence of two [S P ] sulfurs promotes extensive aggregation.

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Section: Methodsmentioning

confidence: 99%

Thiophosphate Analogs of c-di-GMP: Impact on Polymorphism

Zhao

Veliath

Kim

et al. 2009

Nucleosides, Nucleotides & Nucleic Acids

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“…First, the 3Ј,5Ј-disilylated uridine 2 [16] was used as the starting material and transformed into the imidazole-1-carboxylate 3 with carbonyldiimidazole (Scheme 1). First, the 3Ј,5Ј-disilylated uridine 2 [16] was used as the starting material and transformed into the imidazole-1-carboxylate 3 with carbonyldiimidazole (Scheme 1).…”

Section: Synthesis Of Lipophilic Uridinesmentioning

confidence: 99%

“…First, the 3Ј,5Ј-disilylated uridine 2 [16] was used as the starting material and transformed into the imidazole-1-carboxylate 3 with carbonyldiimidazole (Scheme 1). The lipophilic substituents were attached to a 2Ј-hydroxy, 2Ј-amino, or 2Ј-thio function.…”

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confidence: 99%

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Synthesis of Nucleosides with 2′‐Fixed Lipid Anchors and Their Behavior in Phospholipid Membranes

Kaczmarek¹,

Brodersen²,

Bunge³

et al. 2008

Eur J Org Chem

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Various new nucleosides bearing one or two lipophilic groups at the 2′‐position have been synthesized. The lipophilic substituents were attached to a 2′‐hydroxy, 2′‐amino, or 2′‐thio function. These lipophilic nucleosides anchor in large unilamellar POPC vesicles serving as phospholipid membrane models. The insertion of these molecules into the membranes was investigated by NMR techniques. For comparison, nucleosides with two or three lipophilic groups at the 2′‐, 3′‐, or 5′‐positions have also been studied.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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“…The compounds (I) and (II) were synthesized from corresponding nucleosides (Furusawa, Ueno & Katsura, 1990). Colorless prismatic crystals of (I) and (II) by slow evaporation of chloroform solutions.…”

Section: Y X--h (A) X Y (A) H Y (•) X--h Y (°)mentioning

confidence: 99%

Structures of sila analogues of cyclic nucleotides

Ueno¹,

Furusawa²,

Katsura³

1990

Acta Crystallogr C

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RUIZ-PI~REZ, RODRiGUEZ, MARTIN, PI~REZ, MORALES AND RAVELO 1509 located on a difference electron-density map and the remainder placed in calculated positions (Fayos & Martinez-Ripoll, 1980). A convenient weighting scheme of type w = w, x w2 with W 1 = k/(a + blFol) 2 and w2 = 1/{c + d[(sin0)/a] + e[(sin0)/a]2}, was used in order to obtain flat dependence in (w × A2F) vs (Fo} and vs ((sin0)/a) (Martinez-Ripoll & Cano, 1980). A final weighted anisotropic full-matrix refinement (fixed isotropic contribution for H atoms) gave the discrepancy indices: R = 0.069 and wR = 0-077. 136 parameters, S = 1-3, maximum electron density in final difference map 0.20 e A-3, maximum A/tr 0.003. Scattering factors from International Tables for X-ray Crystallography (1974); geometrical calculations using PA RST (Nardelli, 1983).Discussion. Final positional parameters are reported in Table 1.* The molecular structure of the title compound including the atom-numbering scheme is illustrated in Fig. 1. Bond distances, bond angles and relevant torsion angles are shown in Table 2.The six-membered ring C1, C2, C3, C4, C5, C6 is in a distorted chair conformation flattened at C3. Atoms C3 and C6 are displaced by -0.440 (3) ~, z -~; (n) -x, y -~, -z + ~.bisecting the bond between the two out-of-plane atoms (C5--C6) (see Table 2). Fig. 2 gives a representation of the hydrogenbonding scheme around the T along the a axis; donor-acceptor distances are listed in Table 3 Io>2tr(Io)]. The furanose ring is in the twist form, the six-membered silyl ring is in a flattened chair conformation and the glycosidic bond conformation is anti. (II)

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Synthesis and Restricted Conformation of 3′,5′-O-(Di-t-butylsilanediyl)ribonucleosides

Cited by 61 publications

References 16 publications

Thiophosphate Analogs of c-di-GMP: Impact on Polymorphism

Thiophosphate Analogs of c-di-GMP: Impact on Polymorphism

Synthesis of Nucleosides with 2′‐Fixed Lipid Anchors and Their Behavior in Phospholipid Membranes

Structures of sila analogues of cyclic nucleotides

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