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1.
Abstract 2,2′-Anhydro-1-(5,6-di-O-benzoyl-β-D-altrofuranosyl)thymine 6 and uracil derivative 7 are prepared by transformation of the corresponding 5′,6′-di-O-benzoyl-3′-O-mesyl-β-D-glucofuranosyl nucleosides 4 and 5 into the 2,2′-anhydro derivatives 6 and 7 using DBU. 相似文献
2.
Tomoharu Iino Satoshi Shuto Akira Matsuda 《Nucleosides, nucleotides & nucleic acids》2013,32(1-3):169-181
Abstract A synthetic method for (2′S)-2′-C-alkyl-2′-deoxyuridines (9) has been described. Catalytic hydrogenation of 1-[2-C-alkynyl-2-O-methoxalyl-3,5-O-TIPDS-β-D-arabino-pentofuranosyl]uracils (5) gave 1-[2-C-(2-alkyl)-2-O-methoxalyl-3,5-O-TIPDS-β-D-arabino-pentofuranosyl]uracils (4) as a major product, which were then subjected to the radical deoxygenation, affording (2′S)-2′-alkyl-2′-deoxy-3′,5′-O-TIPDS-uridines (7) along with a small amount of their 2′R epimers. 相似文献
3.
Yukio Aoyama Takeshi Sekine Yoshiaki Iwamoto Etsuko Kawashima Yoshiharu Ishido 《Nucleosides, nucleotides & nucleic acids》2013,32(1-3):733-738
Abstract Efficient syntheses of 2′-bromo-2′-deoxy-3′,5′-O-TPDS-uridine (5a) and 1-(2-bromo-3,5-O-TPDS-β-D-ribofuranosyl)thymine (5b) from uridine and 1-(β-D-ribofuranosyl)thymine are described, respectively. The key step is a treatment of 3′,5′-O-TPDS-O2,2′-anhydro-1-(β-D-ardbinofuranosyl)uracil (4a) and -thymine (4b) with LiBr in the presence of BF3-OEt2 in 1,4-dioxane at 60°C to give 5a and 5b in 98%, and 96% yield, respectively. 相似文献
4.
Pawel Lipka Andrzej Zatorski Kyoichi A. Watanabe Krzysztof W. Pankeiwicz 《Nucleosides, nucleotides & nucleic acids》2013,32(1-3):149-167
Abstract 5-O-tert-Butyldimethylsilyl-1,2-O-isopropylidene-3(R)-(nicotinamid-2-ylmethyl)-α-D-ribofuranose (11a) and ?3(R)-(nicotinamid-6-ylmethyl)-α-D-ribofuranose (11b) were prepared by condensation of 5-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-α-D-erythro-3-pentulofuranose (10) with lithiated (LDA) 2-methylnicotinamide and 6-methylnicotinamide, respectively, and then deprotected to give 1,2-O-isopropylidene-3-(R)-(nicotinamid-2-ylmethyl)-α-D-ribofuranose(12a) and 1,2-O-isopropylidene-3(R)-(nicotinamid-6-ylmethyl)-α-D-ribofuranose (12b). Benzoylation as well as phosphorylation of compounds 12 afforded the corresponding 5-O-benzoate (13b) and 5-O-monophosphates (14a and 14b). Treatment of 13b with CF3COOH/H2O caused 1,2-de-O-isopropylidenation with simultaneous cyclization to the corresponding methylene-bridged cyclic nucleoside - 3′,6-methylene-1-(5-O-benzoyl-β-D-ribofuranose)-3-carboxamidopyridinium trifluoro-acetate (8b) - restricted to the “anti” conformation. In a similar manner compounds 14a and 14b were converted into conformationally restricted 2,3′-methylene-1-(β-D-ribofuranose)-3-carboxamidopyridinium-5′-monophosphate (9a - “syn”) and 3′,6-methylene-1-(β-D-ribofuranose)-3-carboxamido -pyridinium-5′monophosphate (9b - “anti”) respectively. Coupling of derivatives 12a and 12b with the adenosine 5′-methylenediphosphonate (16) afforded the corresponding dinucleotides 17. Upon acidic 1,2-de-O-isopropylidenation of 17b, the conformationally restricted P1-[6,3′-methylene-1-(β-D-ribofuranos-5-yl)-3-carboxamidopyridinium]-P2-(adenosin-5′-yl)methylenediphosphonate 18b -“anti” was formed. Compound 18b was found to be unstable. Upon addition of water 18b was converted into the anomeric mixture of acyclic dinucleotides, i. e. P1-[3(R)-nicotinamid-6-ylmethyl-D-ribofuranos-5-yl]-P2-(adenosin-5′-yl)-methylenediphosphonate (19b). In a similar manner, treatment of 17a with CF3COOH/H2O and HPLC purification afforded the corresponding dinucleotide 19a. 相似文献
5.
Kyu-Min Kim Jin-Soo Park HaeRi Choi Min-Seon Kim Joo-Hyun Seo 《Biocatalysis and Biotransformation》2013,31(6):469-475
AbstractBiotransformation of daidzein was performed by using Bacillus amyloliquefaciens KCTC 13588, Lactococcus lactis subsp. lactis KCTC 3769, Leuconostoc citreum KCTC 13186, Kluyveromyces lactis var. lactis KCTC 17704, Pediococcus pentosaceus KCTC 3116, and Lactobacillus sakei KCTC 13416 cells as a biocatalyst. Four derivatives of daidzein such as daidzein-7-O-phosphate, daidzein-7-O-β-D-glucoside, daidzein-7-O-β-(6′′-O-succinyl)-D-glucoside, and 4′-Ethoxy-daidzein-7-O-β-(6′′-O-succinyl)-D-glucoside were isolated from the biotransformation reaction mixture. The structures of the molecules were elucidated by HPLC, HR-QTOF-ESI/MS and 1H-NMR analyses. Among them 4′-Ethoxy-daidzein-7-O-β-(6′′-O-succinyl)-D-glucoside derivative is novel compound and not reported elsewhere till now. 相似文献
6.
Abstract 6-Phenyl, 7-phenyl, 6-(4-biphenyl)-, 7-(4-biphenyl)lumazine N1-(2′-deoxy-D-ribofuranosides) were synthesized and incorporated in the different positions of self-complementary oligodeoxyribonucleotides, and the influence of modifications on the melting points of duplexes was studied. 相似文献
7.
Nucleosides VI: A Novel and Convenient Synthesis of Purine S-Cyclonucleosides Via Mitsunobu Reaction
Ji-Wang Chern Chia-Chi Kuo Ming-Jyh Chang Lee-Tai Liu 《Nucleosides, nucleotides & nucleic acids》2013,32(9):941-949
Abstract Two representative S-cyclonucleosides, 8,5′-anhydro-2′, 3′-O-isopropylidene-8-mercaptoadenosine (3) and 8,2′-anhydro-3′,5′-O-(tetraisopropyldisiloxane-1,3-diyl)-8-mercaptoguanosine (8), were prepared in good yields by dropwise addition of one equivalent each of triphenylphosphine and DEAD in DMF into a mixture of 2′,3′-O-isopropylidene-8-mercaptoadenosine (2) or 3′,5′-O-(tetra-iso-propyldisiloxane-1,3-diyl)-8-mercaptoguanosine (7), respectively, in DMF. Treatment of compound 2 with two equivalents each of triphenylphosphine and DEAD in DMF afforded N-[8,5′-anhydro-2′,3′-O-isopropylidene-8-mercaptopurin-6-yl]triphenylphospha-λ5-azene (4) in 87% yield. 相似文献
8.
Hiroshi Shiragami Yasuhiro Tanaka Yumiko Uchida Hisao Iwagami Kunisuke Izawa Toshihide Yukawa 《Nucleosides, nucleotides & nucleic acids》2013,32(2-4):391-400
Abstract Regioselective 2′-O-deacetylation of 9-(2,5-di-O-acetyl-3-bromo-3-deoxy-β-D-xylofuranosyl)adenine (1) is achieved by treatment of 1 with β-cyclodextrin (β-CyD) / aq. NaHCO3 or N2H4·H2O / EtOH. The 9-(5-O-Acetyl-3-bromo-3-deoxy-β-D-xylo-furanosyl)adenine (2) obtained is a common intermediate for the synthesis of 2′,3′-dideoxy-adenosine (ddA) (7) and 9-(2-fluoro-2,3-dideoxy-β-D-threo-pentofuranosyl)-adenine (F-ddA) (9). 相似文献
9.
Abstract The first synthesis of nitro-multideoxy-sugar containing nucleosides was achieved. 1-(4,6-O-Benzylidene-3-deoxy-3-nitro-β-D-glucopyranosyl)uracil (3) was converted in 75% yield into 1-(4,6-O-benzylidene-2,3-dideoxy-3-nitro-arabinohexopyranosyl)uracil (7) by acetylation followed by NaBH4 reduction in methanol. De-O-benzylidenation with CF3CO2H afforded crystalline 1-(2,3-dideoxy-3-nitro-β-D-arabinohexopyranosyl)uracil (S) was obtained in 87% yield. Raney Ni reduction of 8 afforded the corresponding 3′-amino-nucleoside 9. Acetylation of 8 followed by NaBH4 treatment afforded an 8:1 mixture from which 1-(2,3,4-trideoxy-3-nitro-β-D-threohexopyranosyl)-uracil (14) was obtained in pure crystalline form. After Raney Ni reduction of the mixture, 1-(3-amino-2,3,4-trideoxy-β-d-threo-hexopyranosyl)uracil (16) and its erythro epimer 21 were isolated. 1-(4,6-O-Benzylidene-2,3-dideoxy-3-nitro-β-d-lyxohexopyranosyl)uracil (24) was prepared in 72% yield from 1-(4,6-O-benzylidene-3-deoxy-3-nitro-β-d-galactopyranosyl)uracil (4) by acetylation and subsequent reduction with NaBH4. De-O-benzylid-enation of 23 afforded 1-(2,3,4-trideoxy-3-nitro-β-d-lyxohexopyranosyl)uracil (25) in 83% yield. Schmidt-Rutz reaction of 25 followed by NaBH4 reduction afforded a mixture of threo and elythro isomers of 2′,3′,4′-trideoxy-3′-nitro-hexopyranosyluracil, from which pure 16 and 21 were obtained. 相似文献
10.
Brian A. Otter Shirish A. Patil Marianne R. Spada Linda A. Jelicks Yuichi Yoshimura Akira Matsuda 《Nucleosides, nucleotides & nucleic acids》2013,32(2-4):615-635
Abstract The 5-oxo-6-methylene-pyrimidine-2,4-dione intermediate (6) that is formed when 5-acetoxy-6-acetoxymethyl-1-β-D-(5-O-acetyl-2,3-O-isopropylidene)-ribofuranosyluracil (5) is treated with sodium hydroxide undergoes cyclization at pH 14 to give 2′,3′-O-isopropylidene-5-hydroxy- O 5, 6-methanouridine (8) in good yield. Conversion of 8 into the 5-triflate ester 14 followed by reduction with [(Ph)3P]4Pd/Bu3SnH and deblocking with acetic acid then affords O 5′, 6-methanouridine (4) Conformational studies (NOE difference spectra, vicinal 1H-13C coupling constants, NOESY and CD spectra, molecular modeling) indicate that the C7-methylene group of 4 projects towards the furanose ring oxygen atom, producing a glycosyl rotation angle of about ? 160°. 相似文献
11.
Tun-Cheng Chien David A. Berry John C. Drach Leroy B. Townsend 《Nucleosides, nucleotides & nucleic acids》2013,32(10-12):1971-1996
3-Amino-6-(β-D-ribofuranosyl)imidazo[4,5-c]pyrazole (2) was synthesized via an N-N bond formation strategy by a mononuclear heterocyclic rearrangement (MHR). A series of 5-amino-1-(5-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-β-D-ribofuranosyl-4-(1,2,4-oxadiazol-3-yl)imidaz-oles (6a-d), with different substituents at the 5-position of the 1,2,4-oxadiazole, were synthesized from 5-amino-1-(β-D-ribofuranosyl)imidazole-4-carboxamide (AICA Ribose, 3). It was found that 5-amino-1-(5-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-4-(5-methyl-1,2,4-oxadiazol-3-yl)imidazole (6a) underwent the MHR with sodium hydride in DMF or DMSO to afford the corresponding 3-acetamidoimidazo[4,5-c]pyrazole nucleoside(s) (7b and/or 7a) in good yields. A direct removal of the acetyl group from 3-acetamidoimidazo[4,5-c]pyrazoles under numerous conditions was unsuccessful. Subsequent protecting group manipulations afforded the desired 3-amino-6-(β-D-ribofuranosyl)imidazo[4,5-c]pyrazole (2) as a 5:5 fused analog of adenosine (1). 相似文献
12.
Abstract 3′-Amino-3′-deoxy-5′-O-(4,4′-dimethoxytrityl)-3′-N,5′(R)-C-ethylenethymidine (6) was synthesized starting from 3′-azido-3′-deoxythymidine. Condensation of 6 with 5′-O-(H-phosphonyl)thymidine and 5′-O-(p-nitrophenoxycarbonyl)thymidine derivatives gave dinucleotide and dinucleoside derivatives, respectively, which were incorporated into oligodeoxynucleotides (ODNs). Tm data of the modified ODNs are also presented. 相似文献
13.
Wojciech T. Markiewicz Anna Niewczyk Zofia Gdaniec Dorota A. Adamiak Zbigniew Dauter Wojciech Rypniewski 《Nucleosides, nucleotides & nucleic acids》2013,32(1-3):411-424
Abstract Minor nucleosides found in several eukaryotic initiator tRNAsi Met, O-β-D-ribofuranosyl(1″→2′)adenosine and -guanosine (Ar and Gr), as well as their pyrimidine analogues, were obtained from N-protected 3′,5′-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)ribonucleosides and 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose in the presence of tin tetrachloride in 1,2-dichloroethane. A crystal structure has been solved for 2′-O-ribosyluridine. The 3′-phosphoramidites of protected 2′-O-ribosylribonucleosides were prepared as the reagents for 2′-O-ribofuranosyloligonucleotides synthesis. O-β-D-Ribofuranosyl(1″→2′)adenylyl(3′→5′)guanosine (ArpG) was obtained and its structure was analysed by NMR spectroscopy. 相似文献
14.
Shalini Misra Sudha Jain K. Avasthi D. S. Bhakuni 《Nucleosides, nucleotides & nucleic acids》2013,32(6):837-846
Abstract 4-Amino-6-methylthio-1-(3′-deoxy-β-D-ribofuranosyl)-1H-pyrazolo-[3, 4-d]pyrimidine (11) and 6-methylthio-4(5H)-oxo-1-(3′-deoxy-β-D-ribofuranosyl)-1H-pyrazolo[3, 4-d]pyrimidine (12) have been synthesized from 1, 2-di-O-acetyl-5-O-benzoyl-3-deoxyribofuranose (5) and 4, 6-bis (methylthio)-1H-pyrazolo-[3, 4-d]pyrimidine (6). in a convergent fashion. Structural proofs are based on MS, IR, 1H NMR, 13C NMR and elemental analyses. 相似文献
15.
Abstract The 2′-O-methylisocytidine phosphoramidite synthon 7 and methylphosphonamidite synthon 8 are synthesized from 2′-O-methyluridine. The N2 -(N′, N′-dimethylformamidine) protected 2′-O-methylisocytidine is stable to basic deamination and acidic depyrimidination. Synthon 7 and synthon 8 have been incorporated into oligomers via the automated solid state procedure. 相似文献
16.
A. Burdzy B. Skalski S. Paszyc Z. Gdaniec R. W. Adamiak 《Nucleosides, nucleotides & nucleic acids》2013,32(1-3):143-151
Abstract Optimized conditions for photosensitized preparation of green-yellow fluorescent (λEm = 530 nm) 7-β-D-ribofuranosylamino)pyrido[2,1 -h]pteridin-11-ium-5-olate (luminarosine) and its 2′-deoxy- and 2′-O-methyl- analogues, the key compounds in our studies on the synthesis of fluorescence-labeled oligonucleotides, have been developed. 相似文献
17.
Keiichi Aritomo Chihiro Urashima Takeshi Wada Mitsuo Sekine 《Nucleosides, nucleotides & nucleic acids》2013,32(1-3):1-16
Abstract Reaction of 2′,3′,5′-O-silylated inosine derivative 1 with 2, 3-O-isopropylidene-5-O-tritylribosyl chloride (3) in a two-phase (CH2Cl2-aq. NaOH) system in the presence of Bu4NBr gave three products, i. e., 6-O-α-, 6-O-β-, and N 1-β-isomers of glycosides 4, 5a, and 5b. A similar PTC reaction of 1 with 2, 3, 5-tri-O-benzylribosyl bromide (9) gave four regio- and stereo-isomers involving the N1-β-glycoside 10. Reaction of 1 with 2, 3, 5-tri-O-benzoylribosyl bromide (11) afforded three products involving the desired N1-β-glycoside 12b, which could be deprotected to give N 1-ribosylinosine (15b) as a useful intermediate for the synthesis of cIDPR. 相似文献
18.
Andrei A. Rodionov Ekaterina V. Efimtseva Sergey N. Mikhailov 《Nucleosides, nucleotides & nucleic acids》2013,32(4-5):623-624
Abstract The first synthesis of O-β-D-ribofuranosyl-(1″-2′)-adenosine-5″-O-phosphate starting from protected 2′-O-β-D-ribofuranosyladenosine has been performed. 相似文献
19.
《Nucleosides, nucleotides & nucleic acids》2013,32(5-8):1117-1118
Abstract The efficient synthesis of oligonucleotides containing 2′-O-β-D-ribofuranosyl (and β-D-ribopyranosyl)nucleosides, 2′-O-α-D-arabinofuranosyl (and α-L-arabinofuranosyl)nucleosides, 2′-O-β-D-erythrofuranosylnucleosides, and 2′-O-(5′-amino-5-deoxy-β-D-ribofuranosyl)nucleosides have been developed. 相似文献
20.
Hiroyasu Kumamoto Yoshiharu Matsubara Yoshitomi Iizuka Kozo Okamoto Katsumi Yokoi 《Bioscience, biotechnology, and biochemistry》2013,77(9):2613-2618
An attempt was made to isolate the hypotensive substances from a hot water extract of kinkan. Eight flavonoid glycosides were isolated by repeated chromatography and by gel filtration after extracting with n-butanol and treating with lead subacetate. Their structures were established to be 6,8-di-C-glucosylapigenin (1), 3,6-di-C-glucosylacacetin (2), 2″-O-α-l-rhamnosyl-4′-O-methyl-vitexin (3), 2″-O-α-l-rhamnosyl-4′-O-methylisovitexin (4), 2″-O-α-l-rhamnosylvitexin (5), 2″-O-α-l-rhamnosylorientin (6), 2″-O-α-l-rhamnosyl-4′-O-methylorientin (7) and ponicilin (8) by UV. MS, 1-NMR and 13C-NMR spectroscopy, and by sugar analysis. Each component was intravenously injected in SHR-SP (0.5 ~ 1.0 mg/100 g of body weight), 1, 2, 5 and 6 were found to lower the rat blood pressure.Among these compounds, 2, 3, 4, 6 and 7 were new flavone glycosides. 相似文献