共查询到20条相似文献,搜索用时 302 毫秒
1.
Takeshi Wada Yuichi Sato Fumio Honda Shun-Ichi Kawahara Akira Mochizuki Mitsuo Sekine 《Nucleosides, nucleotides & nucleic acids》2013,32(6-7):1225-1226
Abstract Oligodexyribonucleotides were synthesized by using N-unprotected H-phosphonate monomers and a phosphonium-type of new condensing reagent. In the present H-phosphonate approach, N-sulfonyloxaziridine derivatives were successfully employed as new reagents for oxidation of the H-phosphonate linkages in the presence of silylating reagents. 相似文献
2.
Michal Sobkowski Malgorzata Wenska Adam Kraszewski Jacek Stawiński 《Nucleosides, nucleotides & nucleic acids》2013,32(10-12):1487-1503
Abstract Reactions of nucleoside H-phosphonates with various diols using different types of condensing agents have been studied. Depending on the coupling procedure and the length of a polymethylene chain of the diol, acyclic H-phosphonate diesters or cyclic phosphite triesters were formed. The course of oxidation with iodine to produce cyclic nucleoside alkyl phosphotriesters or hydroxyalkyl nucleoside phosphodiesters can be controlled by the amount of water present in the reaction medium. 相似文献
3.
《Nucleosides, nucleotides & nucleic acids》2013,32(5-8):895-897
Abstract The synthesis, anti-HIV activity and stability studies of a H-phosphonamidate derivative of 3′-azido-2′,3′-dideoxythymidine (AZT) incorporating a N,N-diisopropylamino residue as first model of alkylamino group are reported. The results demonstrate that such phosphorylated structure exerts its biological effects via chemical hydrolysis into the corresponding H-phosphonate, precursor of the parent nucleoside. 相似文献
4.
Michal Sobkowski Jadwiga Jankowska Adam Kraszewski Jacek Stawinski 《Nucleosides, nucleotides & nucleic acids》2013,32(10-12):1469-1484
Sixteen diribonucleoside (3′-5′)-H-phosphonates were synthesized via condensation of the protected ribonucleoside 3′-H-phosphonates with nucleosides, and the influence of a nucleoside sequence on the observed stereoselectivity was analyzed. 31P NMR spectroscopy was used to evaluate a relationship between chemical shift and absolute configuration at the phosphorous center of the H-phosphonate diesters as well as of the corresponding phosphorothioate diesters. Although for the most cases such correlation was found, there was however several exceptions to the rule where the relative positions of resonances arising from R P and S P diastereomers were reversed. 相似文献
5.
Abstract The synthesis of a potential new prodrug system for the antiviral nucleoside ddU 1 based on α-hydroxybenzylphosphonates 2 and 3 is described. In principle, 2, 3 are able to hydrolyze via different mechanisms yielding ddU H-phosphonate 4 or ddU monophosphate 5, respectively. 相似文献
6.
Abstract The tetraribonucleoside triphosphate 15 and the cyclic tetraribonucleotide 16 have been prepared by a recently reported triester approach in solution, involving H-phosphonate coupling. 相似文献
7.
Abstract 31P NMR Studies on the conversion of nucleoside H-phosphonate monoesters into the corresponding H-phosphonothioates revealed that the key intermediate, the nucleoside trimethylsilyl pivaloyl phosphite 3, may undergo under the reaction conditions at least two parallel transformations to, most likely, the nucleoside trimethylsilyl chlorophosphite 6 and the monosilylated nucleoside H-phosphonate 5. 相似文献
8.
Abstract A new approach, based on the use of 3′-H-phosphonate building blocks, is described for the synthesis of oligonucleotides and their phosphorothioate analogues in solution. 相似文献
9.
Osamu Sakatsume Hiroshi Yamane Hiroshi Takaku 《Nucleosides, nucleotides & nucleic acids》2013,32(5-6):1033-1036
Abstract Bis (1, 1, 1, 3, 3, 3-hexafluoro-2-propyl) phosphonate was most promising as a phosphonylating agent for the preparation of nucleoside-3′-phosphonate units. 1, 3-Dimethyl-2-chloro-imida-zolinium chloride (UWC) as a coupling agent has successfully been used for the internucleotidic H-phosphonate bonds formation via the H-phosphonate approach on a solid support. 相似文献
10.
O. V. Sizova S. D. Mal'tsev V. N. Shibaev 《Russian Journal of Bioorganic Chemistry》2003,29(4):387-389
An improved method for the synthesis of dolichyl H-phosphonate was developed using 2-chloro-4H-1,3,2-benzodioxaphosphorin-4-one (salicyl chlorophosphite) as a reagent. Dolichyl phosphorofluoridate was for the first time synthesized from dolichyl H-phosphonate by its treatment with chlorotrimethylsilane,followed by oxidation with iodine in the presence of fluoride in pyridine. 相似文献
11.
Annika Kers Inger Kers Jacek Cieslak Adam Kraszewski Jacek Stawinski 《Nucleosides, nucleotides & nucleic acids》2013,32(4-5):991-992
Abstract Various aspects of oxidative coupling of nucleoside aryl H-phosphonate diesters with nucleosides to produce important synthetic intermediates in the phosphotriester approach to oligonucleotide synthesis, dinucleoside aryl phosphotriesters, was investigated. 相似文献
12.
Abstract Two procedures for the preparation of 2′-deoxy-iso-inosine (1) are presented. Synthesis of 3′-phosphoramidite (7) and 3′-phosphonate (8) derivatives are described, as well as an oligodeoxynucleotide containing iso-I. 相似文献
13.
《Nucleosides, nucleotides & nucleic acids》2013,32(4-7):1043-1045
The ring-expanded (“fat”) nucleoside, 4,8-diamino-6-imino-6H-1-β-D-ribo- furanosylimidazo[4,5-e][1,3]diazepine (1) and its 2′,3′,5′-tri-O-benzoyl derivative (2) exhibited potent broad spectrum anticancer activities in vitro against a wide variety of human tumor cell lines. The tribenzoyl derivative 2 was found to be considerably more active than the parent nucleoside 1. Further studies using human prostate cancer cells PC-3 and DU-145 suggest that the treatment of exponentially growing culture cells with 1 and 2 leads to marked loss of cell viability in a dose-dependent manner. 相似文献
14.
15.
Weidong Hu Qinghua Yang Shuyang Wang Gang Huang Yueteng Zhang Jingjing Dong 《Nucleosides, nucleotides & nucleic acids》2013,32(7):389-395
A new route for the synthesis of the anti-HCV nucleoside analogue, 4-amino-5-fluoro-7-(2′-deoxy-2′-fluoro-2′-C-methyl-β-d-ribofuranosyl)-1H-pyrrolo[2,3-d]pyrimidine 1, was developed. 相似文献
16.
N. Nguyen-ba L. Chan M. Quimpère N. Turcotte N. Lee H. Mitchell 《Nucleosides, nucleotides & nucleic acids》2013,32(4-5):821-827
Abstract We have developed a novel class of 2-phosphonate 1,3-dioxolane nucleotide analogues, from which the guanine derivative displayed weak anti-HCMV activity. Further SAR studies led to the identification of both cis and trans guanine derivatives of tetrahydrofuran analogues as potent anti-HCMV agents, both in vitro and in vivo, compared to ganciclovir and HPMPC. 相似文献
17.
Radhakrishnan P. Iyer Dong Yu Theresa Devlin Nan-Hui Ho Suzanne Johnson Sudhir Agrawal 《Nucleosides, nucleotides & nucleic acids》2013,32(7-9):1491-1495
Abstract Mixed backbone oligonucleotides (MBOs) (containing ionic and non-ionic internucleotidic linkages) in which the non-ionic segments are either methylphosphotriester (PO-OMe) or primary phosphoramidate (PO-NH2) linkages have been prepared using the recently described N-pent-4-enoyl (PNT) nucleoside phosphoramidates and H-phosphonates. Biophysical properties and stability studies suggest that these MBOs are novel antisense molecules. 相似文献
18.
Olga Adelfinskaya Weidong Wu V. Jo Davisson Donald E. Bergstrom 《Nucleosides, nucleotides & nucleic acids》2013,32(10-12):1919-1945
Two novel C-linked oxadiazole carboxamide nucleosides 5-(2′-deoxy-3′,5′-β-D-erythro-pentofuranosyl)-1,2,4-oxadiazole-5-carboxamide (1) and 5-(2′-deoxy-3′,5′-β-D-erythro-pentofuranosyl)-1,2,4-oxadiazole-3-carboxamide (2) were successfully synthesized and characterized by X-ray crystallography. The crystallographic analysis shows that both unnatural nucleoside analogs 1 and 2 adapt the C2′-endo (“south”) conformation. The orientation of the oxadiazole carboxamide nucleobase moiety was determined as anti (conformer A) and high anti (conformer B) in the case of the nucleoside analog 1 whereas the syn conformation is adapted by the unnatural nucleoside 2. Furthermore, nucleoside analogs 1 and 2 were converted with high efficiency to corresponding nucleoside triphosphates through the combination chemo-enzymatic approach. Oxadiazole carboxamide deoxyribonucleoside analogs represent valuable tools to study DNA polymerase recognition, fidelity of nucleotide incorporation, and extension. 相似文献
19.
Henrik M. Pfundheller Poul Nielsen Jesper Wengel 《Nucleosides, nucleotides & nucleic acids》2013,32(7-9):1439-1442
Abstract The stereoselective synthesis of 3′-C-Allyluridine derivative 2 has been accomplished. This nucleoside was used as a key synthon for the synthesis of oligodeoxynucleotides containing 3′-C-(3-benzoyloxypropyl)thymidine (X) or bicyclo nucleoside (Y+Z) monomers. Preliminary thermal experiments are reported. 相似文献
20.
《Nucleosides, nucleotides & nucleic acids》2013,32(5-8):1411-1413
Abstract Dialkyl(cyanomethyl)ammonium salts 1 were synthesized and used as a novel class of activators for the stereospecific condensations of diastereopure nucleoside 3′-O-oxazaphospholidines with a nucleoside. This new oxazaphospholidine method could efficiently produce both (Rp)- and (Sp)-dinucleoside phosphorothioates. 相似文献