- The development of β-selective glycosylation reactions with benzyl substituted 2-deoxy-1,4-dithio-D-erythro-pentofuranosides: enabling practical multi-gram syntheses of 4'-Thio-2'-deoxycytidine (T-dCyd) and 5-aza-4’-thio-2’-deoxycytidine (aza-T-dCyd) to s
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The lack of effective methods to perform direct β-selective glycosylation reactions with 2-deoxy-1,4-dithio-D-erythro-pentofuranosides has long been a significant stumbling block for the multi-gram synthesis of 4’-thio-2’-deoxy nucleosides. In addition, p
- Wishka, Donn G.,Lopez, Omar D.,Rudchenko, Vladimir F.,Huang, Guangfei,Bahde, Robert,Kumar, Vineet,Denysenko, Sergiy M.,Zhang, Lianhao,Zhang, Mianji,Teicher, Beverly A.,Morris, Joel
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- SYNTHETIC INTERMEDIATE OF 1-(2-DEOXY-2-FLUORO-4-THIO-?-D-ARABINOFURANOSYL)CYTOSINE, SYNTHETIC INTERMEDIATE OF THIONUCLEOSIDE, AND METHOD FOR PRODUCING THE SAME
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A compound represented by a formula [1D] as shown below (wherein R1A, R1B, R2A, R2B, R3A and R3B represent a hydrogen atom, an optionally substituted C1-6 alkyl group, and the li
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Paragraph 1634-1636
(2015/06/10)
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- Synthesis and DNA/RNA Binding Properties of Conformationally Constrained Pyrrolidinyl PNA with a Tetrahydrofuran Backbone Deriving from Deoxyribose
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Sugar-derived cyclic β-amino acids are important building blocks for designing of foldamers and other biomimetic structures. We report herein the first synthesis of a C-activated N-Fmoc-protected trans-(2S,3S)-3-aminotetrahydrofuran-2-carboxylic acid as a building block for Fmoc solid phase peptide synthesis. Starting from 2-deoxy-d-ribose, the product is obtained in a 6.7% overall yield following an 11-step reaction sequence. The tetrahydrofuran amino acid is used as a building block for a new peptide nucleic acid (PNA), which exhibits excellent DNA binding affinity with high specificity. It also shows preference for binding to DNA over RNA and specifically in the antiparallel orientation. In addition, the presence of the hydrophilic tetrahydrofuran ring in the PNA structure reduces nonspecific interactions and self-aggregation, which is a common problem in PNA due to its hydrophobic nature.
- Sriwarom, Pitchanun,Padungros, Panuwat,Vilaivan, Tirayut
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p. 7058 - 7065
(2015/07/28)
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- Differential solvation and tautomer stability of a model base pair within the minor and major grooves of DNA
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2-(2′-Hydroxyphenyl)benzoxazole (HBO) may be used as a model base pair to study solvation, duplex environment, and tautomerization within the major and minor groves of DNA duplexes. In its ground state, HBO possesses an enol moiety which may be oriented s
- Dupradeau, Francois-Yves,Case, David A.,Yu, Chengzhi,Jimenez, Ralph,Romesberg, Floyd E.
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p. 15612 - 15617
(2007/10/03)
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- Preparation of new acylated derivatives of L-arabinofuranose and 2-deoxy-L-erythro-pentofuranose as precursors for the synthesis of L-pentofuranosyl nucleosides
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1,2-Di-O-acetyl-3,5-di-O-benzoyl-L-rabinofuranose and 1-O-acetyl-3,5-di-O-benzoyl-2-deoxy-L-erythro-pentofuranose have been synthesised from L-rabinose for use in the preparation of L-pentofuranosyl nucleosides. 1,2-Di-O-acetyl-3,5-di-O-benzoyl-L-arabinof
- Genu-Dellac,Gosselin,Imbach
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p. 249 - 255
(2007/10/02)
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- Improved procedure for the regiospecific synthesis of 2'-deoxyribonucleosides
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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
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p. 4437 - 4440
(2007/10/02)
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