共查询到20条相似文献,搜索用时 0 毫秒
1.
Ralf P. Mauritz Chris Meier Eugen Uhlmann 《Nucleosides, nucleotides & nucleic acids》2013,32(7-9):1209-1212
Abstract The synthesis of the dimer building blocks 1 and 2 and their introduction into (T)15-oligonucleotides is described. The stability against 3′-exonuclease digestion (SVP) as well as the hybridization properties (Tm values) were examined. 相似文献
2.
《Nucleosides, nucleotides & nucleic acids》2013,32(1-2):51-66
A general synthetic approach to various isoxanthopterin‐nucleosides starting from 6‐methyl‐2‐methylthio‐4(3H), 7(8H)‐pterdinedione (1) has been developed. Ribosylation with 1‐O‐acetyl‐2,3,5‐tri‐O‐benzoyl‐β‐d‐ribofuranose via the silyl‐method led to 2 and reaction with 1‐chloro‐2‐deoxy‐3,5‐di‐O‐p‐toluoyl‐α‐d‐ribofuranose using the DBU‐method afforded 28. Protection of the amide function at O4 by benzylation to 5 and by a Mitsunobu reaction with 2‐(4‐nitrophenyl)ethanol to 29 gave soluble intermediates which can be oxidized to the corresponding 2‐methylsulfonyl derivatives 8 and 30, respectively. Nucleophilic displacement reactions of the highly reactive 2‐methylsulfonyl functions by various amines proceeded under mild conditions to isoxanthopterin‐N8‐ribo‐ (11–17) and 2′‐deoxyribomucleosides (31–33). Debenzylation can be achieve by Pd‐catalyzed hydrogenation (9 to 19) and cleavage of the npe‐protecting group (31, 32 to 34, 35) works well with DBU by β‐elimination. 相似文献
3.
《Nucleosides, nucleotides & nucleic acids》2013,32(5-8):1119-1121
Abstract C8-Arylamine-dG adducts were synthesized by palladium-catalyzed cross- coupling reactions. The corresponding 5′-O-DMTr-3′-O-phosphoramidite-C8-arylamine-dG adducts were synthesized as potential building blocks for the automated synthesis of site-specifically modified oligonucleotides. 相似文献
4.
《Nucleosides, nucleotides & nucleic acids》2013,32(3):531-544
A versatile synthesis of N‐substituted dihydropyrimidinone C‐nucleosides (20–29) is described. Glycosyl amino esters (3–9), obtained by reductive alkylation of glycosyl amino esters 1 and 2, on condensation with different isocyanates afforded respective ureido derivatives (10–19) in good to quantitative yields. The latter on cyclative amidation with a combination of DBU/TBAB (tetrabutylammonium bromide)/4Å molecular sieve gave the corresponding nucleosides (20–29) in good yields. 相似文献
5.
Anna V. Kachalova Timofei S. Zatsepin Elena A. Romanova Dmitry A. Stetsenko Michael J. Gait Tatiana S. Oretskaya 《Nucleosides, nucleotides & nucleic acids》2013,32(10-12):1693-1707
Abstract Chemical syntheses of 2′-O-(allyloxycarbonyl)methyladenosine, 2′-O-(methoxycarbonyl)methyladenosine and 2′-O-(2,3-dibenzoyloxy)propyluridine 3′-2-cyanoethyl-N,N-diisopropyl phosphoramidite building blocks are described. These monomers were used successfully to incorporate carboxylic acid, 1,2-diol and aldehyde functionalities into synthetic oligonucleotides. 相似文献
6.
Cesare Giordano Francesco Pedone Paola Fattibene Luciano Cellai 《Nucleosides, nucleotides & nucleic acids》2013,32(8):1301-1310
Abstract in order to achieve an EPR sensitive probe for DNA, 3-carboxy-Proxyl free radical was linked to O-6 of dG through a five-atoms-tether. The modified base was incorporated into a 30-mer ODN, then annealed to its complementary DNA strand. Hydrodinamic parameters show only a slight destabilization with respect to the equivalent unlabeled hybrid. EPR could monitor the hybrid formation showing a progressive enlargement of the upfield signal in passing from the labeled ss- to the ds-30-mer. 相似文献
7.
D. Bankaitis-Davis L. Huang T. Koga G. Beaton 《Nucleosides, nucleotides & nucleic acids》2013,32(7-9):945-949
Abstract A novel method for the automated synthesis of oligonucleotide-3′-phosphonates is described. Oligonucleotide analogs synthesized by this method exhibited appreciable stability to exonuclease digestion. 相似文献
8.
The chemical modification of the 2′-O-position of nucleosides proved to be of great importance for the RNA stability. Greater stability of RNA duplexes allows a longer half life in the cell and, therefore, a better effect of RNA Interference. Here we investigated the synthesis of 2′-O-aminoethyl adenosine as a cationic modified building block. 相似文献
9.
Synthesis of 5′-Ethynyl-2′-deoxynucleoside Analogues as Building Block for Antisense Oligonucleotide
Hassan B. Lazrek Abdelalli Rochdi Joachim W. Engels 《Nucleosides, nucleotides & nucleic acids》2013,32(6-7):1257-1259
Abstract New nucleosides and nucleoside analogue dimers were prepared using 5′-ethynyl-2′-deoxynucleoside as starting material. 相似文献
10.
Igor A. Mikhailopulo Tamara I. Kulak Olga V. Tkachenko Svetlana L. Sentyureva Frank Seela 《Nucleosides, nucleotides & nucleic acids》2013,32(6-7):1253-1254
Abstract The synthesis of 2′-deoxy-3′-O-phosphonomethyl-α-D-erythro-pentofuranosyl-thymine and -adenine (1, B is Thy or Ade) is described. Dimeric oligonucleotide synthons such as 2 containing isosteric phosphonate internucleoside linkage were prepared. 相似文献
11.
《Nucleosides, nucleotides & nucleic acids》2013,32(5-8):1123-1125
Abstract In general, α-hydroxybenzylphosphonate modified 2′-deoxyadenosine-thymidine dimer building blocks 1, 2 are utilized for the incorporation into α-hydroxybenzylphosphonate pro-oligonucleotides. For a universal application of our pro-oligonucleotide concept on biologically relevant oligonucleotides a route for the synthesis of modified monomer building blocks 3 was developed and is presented herein. 相似文献
12.
Jean Depelley Robert Granet Mourad Kaouadji Pierre Krausz Salomon Piekarski Sylvie Delebassée 《Nucleosides, nucleotides & nucleic acids》2013,32(5):995-1008
Abstract Various 5-alkyl-6-aza-5,6-dihydrouridines and 6-(β-D-ribopyranosyl)-5-alkyl-6-aza-5,6-dihydrouracils have been synthesized. A new regioselective method is described for coupling triazinic bases to the sugar unit. Different epimers were isolated. Antiretroviral activity against Visna virus was evaluated. 相似文献
13.
2′- and 3′- Biotin Conjugated Nucleoside Building Blocks: Synthesis of Biotinylated Oligonucleotides
Muthiah Manoharan Gopal Inamati Kathleen L. Tivel Patrick Wheeler Kim Stecker P. Dan Cook 《Nucleosides, nucleotides & nucleic acids》2013,32(7-9):1411-1413
Abstract The vitamin biotin plays a significant role in biological assays based on its unusually high affinity [KD=10?15M] to streptavidin and avidin. This assay can be used for monitoring cellular trafficking of antisense oligonucleotides using hiotin conjugation. In addition to the above diagnostic application, biotin conjugation to macromolecules could be used as a vitamin-mediated delivery system for macromolecules into cells. Complexation of avidin to hiotin-oligonucleotides (phosphodiesters or PNA) have been used to enhance the uptake of oligonucleotides1. Appropiiate placement of biotin in oligonucleotides could also provide increased nuclease resistance. 相似文献
14.
Eric E. Swayze Balkrishen Bhat Didier Peoc'h Yogesh S. Sanghvi 《Nucleosides, nucleotides & nucleic acids》2013,32(7-9):971-972
Abstract The synthesis of Methylene(methylimino) or MMI linked nucleoside dimers in all sixteen possible configurations has been accomplished via a reductive coupling of a nucleosidic aldehyde with an hydroxylamine. This has allowed us to prepare all of the necessary 2′-O-methyl MMI dimer building blocks necessary for use in an antisense motif. 相似文献
15.
Jacob Ravn Christoph Rosenbohm Signe M. Christensen Troels Koch 《Nucleosides, nucleotides & nucleic acids》2013,32(8):843-847
The first reported synthesis of 2′-amino-LNA purine nucleosides via a transnucleosidation is accomplished enabling the preparation of oligonucleotides incorporating 2′-amino-LNA with all four natural bases. 相似文献
16.
Novel Base-Labile Protecting Groups for 5′-Hydroxy Function in Solid-Phase Oligonucleotide Synthesis
《Nucleosides, nucleotides & nucleic acids》2013,32(5-8):1011-1015
Abstract The 6-(levulinyloxymethyl)-3-methoxy-2-nitrobenzoyl (LMMoNBz) and 2-(levulinyloxymethyl)-5-methoxy-4-nitrobenzoyl (LMMpNBz) groups were developed as novel base-labile protection for the 5′-hydroxy function in solid-phase oligonucleotide synthesis. A comparative study of the LMMoNBz, LMMpNBz and 2-(levulinyloxymethyl)-5-nitrobenzoyl (LMNBz) protecting groups for oligonucleotide synthesis proved strong feasibility for the LMMoNBz group. 相似文献
17.
《Nucleosides, nucleotides & nucleic acids》2013,32(3):211-226
We introduce a novel versatile phosphoramidite building block for the modification of oligonucleotides (ONs) with acyl hydrazides on the 5′- or 3′-terminus, or both. The reaction of these hydrazide functionalized ONs with 4-methoxyphenylaldehyde is demonstrated for solution derivatization. Hydrazides are considered nowadays as promising reactants, which show enhanced reactivity at neutral and slightly acidic conditions and higher stability of yielding products as compared to the aliphatic amines, which are broadly used for ONs derivatization. Our method to introduce hydrazides into ONs employs a phosphoramidite modifier designed to split, during ammonia or lithium hydroxide treatment, into two hydrazides via β-elimination of a central bis-2-carbonylethoxysulfone unit. It allows the creation of ONs derivatized with a hydrazide moiety at the 5′-, 3′- and both 5′- and 3′-termini, as well as two different hydrazide containing ONs at the same time, viz. in one sequence on the same solid support. In latter case one can, for example, synthesize two hydrazide containing ONs, where one is 5′-modified and second one is 3′-modified. 相似文献
18.
Rubusoside derivatives by transgalactosylation of various β-galactosidases were isolated and their structures were analyzed. Escherichia coli β-galactosidase produced mainly 13-O-β-d-glucosyl-19-O-[β-d-galactosyl-(1→6)-β-d-glucosyl]-steviol (RGal-2). Bacillus circulans β-galactosidase produced mainly 13-O-β-d-glucosyl-19-O-[β-d-galactosyl-(1→4)-β-d-glucosyl]-steviol (RGal-1a) in the early stage of the reaction and then produced 13-O-[β-d-galactosyl-(1→4)-β-d-glucosyl]-19-O-β-d-glucosyl-steviol (RGal-1b). With decreasing the amount of these products (RGal-1a and RGal-1b), RGal-2 was produced. 相似文献
19.
Dmitriy S. Esipov Olga V. Esipova Vyacheslav G. Korobko 《Nucleosides, nucleotides & nucleic acids》2013,32(9-11):1697-1704
Abstract A method of completely chemical synthesis of 3′-azido-3′-deoxythymidine-terminated oligonucleotides via 5′-H-phosphonate of AZT is described. 相似文献
20.
Nathalie Batoux Robert Granet Rachida Zerrouki Pierre Krausz 《Nucleosides, nucleotides & nucleic acids》2013,32(9):866-873
The synthesis of a new family of D4T analogues is described to study the influence of pyrazinone base on antiretroviral power. Substitution of 3H by methyl or n-decyl increases the lipophilic character and may facilitate diffusion across cell membranes. The compounds were characterized by 1H NMR and infrared spectroscopy. Antiviral (HIV-1) properties of these compounds were examined. 相似文献