- Synthesis and properties of 3'-deoxypsiconucleosides: Anomeric 1-(3-deoxy-D-erythro-2-hexulofuranosyl)thymines and 9-(3-deoxy-D-erythro-2-hexulofuranosyl)adenines
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Anomeric 1-(3-deoxy-D-erythro-2-hexulofuranosyl)thymines and 9(3-deoxy-D-erythro-2-hexulofuranosyl)adenines were prepared by tin(IV) chloride catalyzed N-glycosylation of trimethylsilylated thymine and N6-benzoyladenine with methyl 3-deoxy-D-er
- Alzhayev,Guzaev,Hovinen,Mattinen,Sillanpaa,Lonnberg
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Read Online
- An improved synthesis of 2′-O,4′-C-ethylene nucleic acid (ENA) and thermodynamic studies of duplex formation containing the guanosine ENA unit
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Oligonucleotides containing 2′-O,4′-C-ethylene nucleic acids (ENA) have been proven highly effective for antisense therapeutics. 2′-O,4′-C-Ethyleneguanosine and its phosphoramidite were previously obtained from 3,5-di-O-benzy1-4-C-(p-tolulenesulfonyloxyet
- Takagi-Sato, Miho,Morita, Koji,Onishi, Yoshiyuki,Watahiki, Yuuka,Ishigaki, Taku,Akita, Tomoka,Tomita, Erisa,Kawakami, Junji,Koizumi, Makoto
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p. 838 - 852
(2020/02/13)
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- A solid-supported acidic oxazolium perchlorate as an easy-handling catalyst for the synthesis of modified pyrimidine nucleosides via Vorbrüggen-type N-glycosylation
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A solid-supported acidic oxazolium perchlorate was investigated as a heterogeneous catalyst in N-glycosylation reactions using silylated modified pyrimidines and an acylated ribose or glucose to afford the corresponding pyrimidine nucleosides. This salt is a nonhygroscopic and stable powder whose activity is comparable to that of 2-methyl-5-phenylbenzoxazolium perchlorate. A reaction with this polymer catalyst can be conducted on a gram scale. Reusability of the solid-supported catalyst was also investigated.
- Basu, Nabamita,Oyama, Kin-ichi,Tsukamoto, Masaki
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supporting information
p. 1921 - 1924
(2017/04/27)
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- INTERMEDIATE FOR PRODUCTION OF NUCLEOSIDE ANALOGUE, AND METHOD FOR PRODUCING SAME
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A compound represented by the general formula (III) which serves as an intermediate of an oligonucleotide analog having stable and excellent antisense or antigene activity or having excellent activity as a detection reagent (probe) for a specific gene or
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Paragraph 0061
(2015/05/05)
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- Synthesis of deuterated ribo nucleosides N-protected phosphoramidites, and oligonucleotides
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The present invention is directed towards the synthesis of high purity deuterated sugars, deuterated phosphoramidites, deuterated nucleobases, deuterated nucleosides, deuterated oligonucleotides, and deuterated RNA's of defined sequences which can exhibit biochemically useful and biologically valuable properties, thus having potential for therapeutic uses.
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Paragraph 0161
(2014/02/16)
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- Synthesis of 4′-ethynyl-2′-deoxy-4′-thioribonucleosides and discovery of a highly potent and less toxic NRTI
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The synthesis of 4′-ethynyl-2′-deoxy-4′- thioribonucleosides was carried out utilizing an electrophilic glycosidation in which 4-ethynyl-4-thiofuranoid glycal 16 served as a glycosyl donor. Electrophilic glycosidation between 16 and the silylated nucleoba
- Haraguchi, Kazuhiro,Shimada, Hisashi,Kimura, Keigo,Akutsu, Genta,Tanaka, Hiromichi,Abe, Hiroshi,Hamasaki, Takayuki,Baba, Masanori,Gullen, Elizabeth A.,Dutschman, Ginger E.,Cheng, Yung-Chi,Balzarini, Jan
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supporting information; experimental part
p. 692 - 697
(2011/12/02)
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- Synthesis and properties of ApA analogues with shortened phosphonate internucleotide linkage
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A complete series of the 2'-5' and 3'-5' regioisomeric types of r(ApA) and 2'-d(ApA) analogues with the-hydroxy-phosphonate C3'-O-P-CH(OH)-C4" internucleotide linkage, isopolar but non-isosteric with the phosphodiester one, were synthesized and their hybridization properties with polyU studied. Due to the chirality on the 5'-carbon atom of the modified internucleotide linkage bearing phosphorus and hydroxy moieties, each regioisomeric type of ApA dimer is split into epimeric pairs. To examine the role of the 5'-hydroxyl of the-hydroxy-phosphonate moiety during hybridization, the appropriate r(ApA) analogues with 3'(2')-O-P-CH2-C4" linkage lacking the 5'-hydroxyl were synthesized. Nuclear magnetic resonance (NMR) spectroscopy study on the conformation of the modified sugar-phosphate backbone, along with the hybridization measurements, revealed remarkable differences in the stability of complexes with polyU, depending on the 5'-carbon atom configuration. Potential usefulness of the-hydroxy-phosphonate linkage in modified oligoribonucleotides is discussed. Copyright Taylor and Francis Group, LLC.
- Kralikova, Sarka,Budesinsky, Milos,Barvik, Ivan,Masojidkova, Milena,Tocik, Zdenek,Rosenberg, Ivan
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experimental part
p. 524 - 543
(2012/01/02)
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- Synthesis of enantiomerically pure 4-substituted riboses
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An efficient and flexible synthesis of 4-substituted ribose analogues is described. The key step involves the simple addition of a Grignard reagent to a ketone derived from a commercially available ribose. The addition of a range of Grignard reagents proc
- Maddaford, Adrian,Guyot, Thierry,Leese, David,Glen, Rebecca,Hart, James,Zhang, Xiurong,Fisher, Ray,Middleton, Donald S.,Doherty, Cheryl L.,Smith, Nick N.,Pryde, David C.,Sutton, Scott C.
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p. 3149 - 3154
(2008/09/19)
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- Nucleoside 5′-C-phosphonates: reactivity of the α-hydroxyphosphonate moiety
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We found that various dialkyl phosphites, dialkyl trimethylsilyl phosphites, and tris-trimethylsilyl phosphite reacted smoothly with nucleoside 5′-aldehydes to afford epimeric nucleoside 5′-C-phosphonates in high yields. A number of these compounds in bot
- Králíková, ?árka,Budě?ínky, Milo?,Masojídková, Milena,Rosenberg, Ivan
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p. 4917 - 4932
(2007/10/03)
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- Stereoselective synthesis of the β-anomer of 4′-thionucleosides based on electrophilic glycosidation to 4-thiofuranoid glycals
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Three types of 4-thiofuranoid glycal with different 3,5-O-silyl protecting groups were prepared and their electrophilic glycosidation was investigated. The 3,5-bis-O-(tert-butyldimethylsilyl)-4-thiofuranoid glycal (5) was obtained through mesylation of 2-deoxy-4-thio-D-erythro-pentofuranose (4) and subsequent base-promoted elimination, while thermal elimination of sulfoxide derivatives was suitable for the preparation of 3,5-O-(tetraisopropyldisiloxane-1,3-diyl) (9) and 3,5-O-(di-tert-butylsilylene) (11) 4-thioglycals. The glycosidation reactions of these 4-thioglycals were carried out, in the presence of either PhSeCl or NIS, by using silylated derivatives of uracil, thymine, cytosine, and N6-benzoyladenine. Among the three 4-thioglycals, 11 was found to be an excellent glycosyl donor, forming the desired β-anomer exclusively irrespective of the nucleobase employed.
- Haraguchi, Kazuhiro,Takahashi, Haruhiko,Shiina, Noriaki,Horii, Chikafumi,Yoshimura, Yuichi,Nishikawa, Ayako,Sasakura, Eiko,Nakamura, Kazuo T.,Tanaka, Hiromichi
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p. 5919 - 5927
(2007/10/03)
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- Structure-based design, synthesis, and in vitro evaluation of bisubstrate inhibitors for catechol O-methyltransferase (COMT)
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The enzyme catechol O-methyltransferase (COMT) catalyzes the Me group transfer from the cofactor S-adenosylmethionine (SAM) to the hydroxy group of catechol substrates. Potential bisubstrate inhibitors of COMT were developed by structure-based design and synthesized. The compounds were tested for in vitro inhibitory activity against COMT obtained from rat liver, and the inhibition kinetics were examined with regard to the binding sites of cofactor and substrate. One of the designed molecules was found to be a bisubstrate inhibitor of COMT with an IC50 = 2 μM. It exhibits competitive kinetics for the SAM and noncompetitive kinetics for the catechol binding site. Useful structure-activity relationships were established which provide important guidelines for the design of future generations of bisubstrate inhibitors of COMT.
- Masjost, Birgit,Ballmer, Patrick,Borroni, Edilio,Zuercher, Gerhard,Winkler, Fritz K.,Jakob-Roetne, Roland,Diederich, Francois
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p. 971 - 982
(2007/10/03)
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- Synthesis and biological evaluation of cyclophostin: A 5',6-tethered analog of adenophostin A
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The synthesis, conformational analysis and biological evaluation of 5'-6-tethered adenophostin A, so-called cyclophostin 14, and its de-adeninylated analog 15 are described. They are prepared via ring-closing metathesis of diolefin 28, consecutive coupling of the central building block 33 to 6-N-benzoyladenine or propargyl alcohol, respectively, followed by phosphorylation and deprotection. NMR spectroscopy and a molecular dynamics simulation indicated that the 5'-6-tether induces a conformational change from 2'-endolsyn in 1 to 3'-endo/anti in 14. The unexpected small loss of Ca2+-releasing potency of cyclophostin 14, which is reflected by the low EC50/IC50 ratio in comparison with cycloribophostin 15, suggests that the interaction of the adenine with IP3R plays a decisive role in determining the high activity of adenophostin A (1). (C) 2000 Elsevier Science Ltd.
- De Kort, Martin,Regenbogen, Anouk D.,Overkleeft, Herman S.,John Challiss,Iwata, Yoriko,Miyamoto, Shuichi,Van der Marel, Gijs A.,Van Boom, Jacques H.
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p. 5915 - 5928
(2007/10/03)
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- Synthesis and antifungal activity of 3'-deoxyribonucleosides
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Synthesis and antifungal activity of 3'-deoxyribonucleosides containing naturally occurring pyrimidine and purine bases are reported.
- Kumar,Khan,Manglani,Khan,Katti
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p. 1049 - 1058
(2007/10/02)
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- Synthetic approaches to novel cis and trans dideoxynucleosides of the apiose family
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Stereoselective synthesis of the complete family of optically active dideoxygenated nucleosides of the apiose family have been developed. The chiral aldodiol system 7, a key intermediate in this synthesis, was prepared from the prochiral molecule 6, through the action of the lipase from Candida cylindracia. Approaches to novel enantiomeric and diastereoisomeric dideoxynucleosides containing the tetrahydrofuranethanol moiety have also been discovered. A key intermediate in this approach was the optically active trans-allyllactone 61, prepared from L-glutamic acid, and its isomerization product, the corresponding cis-allylbutyrolactone 62. The methodologies developed have generality and allow synthetic access to a wide variety of new nucleosides.
- Sells, Todd B.,Nair, Vasu
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p. 117 - 138
(2007/10/02)
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- Synthesis of 4'-C-methylnucleosides.
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Several 4'-C-methylnucleosides were prepared. 1H-NMR studies on these nucleotides showed that they have the 3'-exo furanose ring conformation different from the 3'-endo conformation of natural nucleosides.
- Waga,Nishizaki,Miyakawa,Ohrui,Meguro
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p. 1433 - 1438
(2007/10/02)
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