- Photocycloaddition of benzoylated 2'-deoxyribonucleoside to 2,3-dimethyl-2-butene
-
The photochemical reactions of 3',5'-dibenzoyl-2'-deoxyuridine and -thymidine with 2,3-dimethyl-2-butene by upon ultraviolet (UV) irradiation in acetone have been investigated. Each reactant gave a pair of diastereomers in good yield. After recrystallization, mixed crystals of diastereomers could be isolated and purified. An X-ray analysis of a mixed crystal of the thymidine derivative (3b) showed a pair of diastereomers (A and B) composing a unit cell.
- Li,Sun,Ogura,Konda,Sasaki,Toda,Takayanagi,Harigaya
-
-
Read Online
- Carborane- or Metallacarborane-Linked Nucleotides for Redox Labeling. Orthogonal Multipotential Coding of all Four DNA Bases for Electrochemical Analysis and Sequencing
-
We report a series of 2′-deoxyribonucleoside triphosphates bearing dicarba-nido-undecaborate ([C2B9H11]1-), [3,3′-iron-bis(1,2-dicarbollide)]- (FESAN, [Fe(C2B9H11)2]2-) or [3,3′-cobalt-bis(1,2-dicarbollide)]- (COSAN, [Co(C2B9H11)2]2-) groups prepared either through the Sonogashira cross-coupling or the CuAAC click reaction. The modified dNXTPs were substrates for KOD XL DNA polymerase in enzymatic synthesis of modified DNA through primer extension (PEX). The nido-carborane- and FESAN-modified nucleotides gave analytically useful oxidation signals in square-wave voltammetry and were used for redox labeling of DNA. The redox-modified DNA probes were prepared by PEX using tailed primers and were hybridized to electrode (gold or glassy carbon) containing capture oligonucleotides. The combination of nido-carborane- and FESAN-linked nucleotides with 7-ferrocenylethynyl-7-deaza-dATP and 7-deaza-dGTP allowed polymerase synthesis of DNA fully modified at all four nucleobases, and each of the redox labels gave four differentiable and ratiometric signals in voltammetry. Thus, the combination of these four redox labels constitutes the first fully orthogonal redox coding of all four canonical nucleobases, which can be used for determination of nucleobase composition of short DNA stretches in one simple PEX experiment with electrochemical readout.
- Kodr, David,Yenice, Cansu Pinar,Simonova, Anna,Safti?, Dijana Pavlovi?,Pohl, Radek,Sykorová, Veronika,Ortiz, Mayreli,Havran, Luděk,Fojta, Miroslav,Lesnikowski, Zbigniew J.,O'Sullivan, Ciara K.,Hocek, Michal
-
-
Read Online
- A general method for N-glycosylation of nucleobases promoted by (p-Tol)2SO/Tf2O with thioglycoside as donor
-
Based on a preactivation strategy using the (p-Tol)2SO/Tf2O system, a series of nucleosides were synthesized by coupling various thioglycosides with pyrimidines and purines under mild conditions. High yields and excellent β-stereoselectivities were obtained with either armed or disarmed N-glycosylation donors by tuning the amount of (p-Tol)2SO additive.
- Liu, Guang-Jian,Zhang, Xiao-Tai,Xing, Guo-Wen
-
p. 12803 - 12806
(2015/08/06)
-
- Continuous flow photochemistry for the rapid and selective synthesis of 2′-deoxy and 2′,3′-dideoxynucleosides
-
A new photochemical flow reactor has been developed for the photo-induced electron-transfer deoxygenation reaction to produce 2′-deoxy and 2′,3′-dideoxynucleosides. The continuous flow format significantly improved both the efficiency and selectivity of the reaction, with the streamlined multi-step sequence directly furnishing the highly desired unprotected deoxynucleosides.
- Shen, Bo,Jamison, Timothy F.
-
p. 157 - 164
(2013/04/10)
-
- Continuous flow photocatalysis enhanced using an aluminum mirror: Rapid and selective synthesis of 2′-deoxy and 2′,3′-dideoxynucleosides
-
A unique photochemical flow reactor featuring quartz tubing, an aluminum mirror and temperature control has been developed for the photo-induced electron-transfer deoxygenation reaction to produce 2′-deoxy and 2′,3′-dideoxynucleosides. The continuous flow format significantly increased the efficiency and selectivity of the reaction.
- Shen, Bo,Bedore, Matthew W.,Sniady, Adam,Jamison, Timothy F.
-
supporting information; experimental part
p. 7444 - 7446
(2012/10/08)
-
- Enhanced solubility and selective benzoylation of nucleosides in novel ionic liquid
-
Solubility and benzoylation study of both ribo- and deoxyribonucleosides is reported in a new ionic liquid MoeMIM·TFA; high selectivity for O-benzoylation is achieved.
- Kumar, Vineet,Parmar, Virinder S.,Malhotra, Sanjay V.
-
p. 809 - 812
(2007/10/03)
-
- Benzoyl cyanide: A mild and efficient reagent for benzoylation of nucleosides
-
Efficient benzoylation of various nucleosides has been accomplished in pyridine with a catalytic amount of DMAP and benzoyl cyanide under mild conditions.
- Prasad, Ashok K.,Kumar, Vineet,Maity, Jyotirmoy,Wang, Zhiwei,Ravikumar, Vasulinga T.,Sanghvi, Yogesh S.,Parmar, Virinder S.
-
p. 935 - 945
(2007/10/03)
-
- 'Green' methodology for efficient and selective benzoylation of nucleosides using benzoyl cyanide in an ionic liquid
-
Benzoyl cyanide in the ionic liquid 1-methoxyethyl-3-methylimidazolium methanesulfonate has been employed as a 'green' alternative and mild reaction condition protocol to conventional pyridine-benzoyl chloride system for efficient and selective benzoylation of nucleosides (of both the ribo- and deoxyribo-series) at ambient temperatures. The use of benzoyl cyanide-ionic liquid combination has been successfully extended for highly efficient benzoylation of phenols, aromatic amines, benzyl alcohol, aliphatic diols, 3-aminophenol and 2-aminobenzylalcohol, which indicates the versatility of this benzoylating system.
- Prasad, Ashok K.,Kumar, Vineet,Malhotra, Shashwat,Ravikumar, Vasulinga T.,Sanghvi, Yogesh S.,Parmar, Virinder S.
-
p. 4467 - 4472
(2007/10/03)
-
- Mild, efficient, selective and "green" benzoylation of nucleosides using benzoyl cyanide in ionic liquid
-
Use of benzoyl cyanide (BzCN) for benzoylation of nucleosides has been studied, both in pyridine and in ionic liquid. BzCN in 1-methoxyethyl-3- methylimidazolium methanesulfonate as ionic liquid has been found to be a "green" alternative compared to the pyridine-BzCN system. An efficient and selective benzoylation of nucleosides of both, the 2′-deoxy- and the ribo-series at ambient temperature was accomplished. Copyright Taylor & Francis, Inc.
- Prasad, Ashok K.,Kumar, Vineet,Maity, Jyotirmoy,Sanghvi, Yogesh S.,Ravikumar, Vasulinga T.,Parmar, Virinder S.
-
p. 747 - 751
(2007/10/03)
-
- Stereocontrolled Syntheses of Deoxyribonucleosides via Photoinduced Electron-Transfer Deoxygenation of Benzoyl-Protected Ribo- and Arabinonucleosides
-
The stereocontrolled, de novo syntheses of β-2′-deoxy-, α-2′-deoxy-, β-3′-deoxy-, and β-2′,3′-dideoxyribonucleosides are described. Strategically protected ribose, arabinose, and xylose glycosylation precursors were synthesized bearing C2-esters capable of directing Vorbrueggen glycosylation. The key step is the regioselective deoxygenation of the desired hydroxyl group as either the benzoyl- or 3-(trifluoromethyl)benzoyl derivative. This deoxygenation is accomplished via a photoinduced electron-transfer (PET) mechanism using carbazole derivatives as the photosensitizer. The syntheses of the desired deoxynucleoside generally proceed in three steps from a common, readily available precursor.
- Wang, Zhiwei,Prudhomme, Daniel R.,Buck, Jason R.,Park, Minnie,Rizzo, Carmelo J.
-
p. 5969 - 5985
(2007/10/03)
-
- N-glycosylation with glycosyl diethyl phosphites: A highly stereoselective synthesis of 2′-deoxy-β-ribonucleosides
-
A facile and direct method for the construction of 2′-deoxy-β-N-glycosidic linkages in 2′-deoxyribonucleoside synthesis has been developed by using 3-(3,4,5-trimethoxybenzoyl)-protected 2-deoxyribofuranosyl diethyl phosphites as a glycosyl donor in the presence of trimethylsilyl triflate, wherein coupling reactions with silylated pyrimidine bases have been found to exhibit β-selectivities up to 96%.
- Hashimoto, Shun-Ichi,Inagaki, Jun,Sakamoto, Hiroki,Sano, Ai,Nakajima, Makoto
-
p. 215 - 220
(2007/10/03)
-
- A mild and rapid glycosylation reaction between pyrimidine bases and 2-deoxyribofuranosyl N,N,N',N'-tetramethylphosphoroamidates
-
A trimethylsilyl triflate-mediated coupling reaction to produce protected 2′-deoxynucleosides has been developed by using N,N,N',N'-tetramethylphosphoroamidate as a leaving group. In this reaction, employment of a 3,4,5-trimethoxybenzoyl group as the 3-hydroxyl protective group in the sugar moiety improved the β-stereoselectivity via a novel 1,3-participation.
- Iimori, Takamasa,Kobayashi, Hiroshi,Hashimoto, Shun-Ichi,Ikegami, Shiro
-
p. 485 - 488
(2007/10/03)
-
- Improved procedure for the regiospecific synthesis of 2'-deoxyribonucleosides
-
2'-Deoxyribonucleosides are regiospecifically synthesized in high yields by catalyzing with KI-dibenzo-18-crown-6 PTC the condensation between unprotected silylated purines and pyrimidines and the appropriate easily available 2-deoxy-ribofuranosyl or pyranosyl sugar derivatives.
- Baud,Chavis,Lucas,Imbach
-
p. 4437 - 4440
(2007/10/02)
-