共查询到20条相似文献,搜索用时 15 毫秒
1.
Haruo Tanaka Tadatoshi Hayashi Kiyoshi Nakayama 《Bioscience, biotechnology, and biochemistry》2013,77(7):1731-1736
During the investigation for dephosphorylation of 4-hydroxy-1-β-D-ribofuranosylpyrazolo-[3,4-d] pyrimidine 5′-phosphate, it was found that the compound was converted to an unknown substance by alkaline hydrolysis for 3 hr at 140°C. The structure of the substance was assigned to be 5-amino-1-β-D-ribofuranosylpyrazole-4-carboxamide 5′-phosphate. 5(or3)-Amino- pyrazole-4-carboxamide and its riboside were also obtained from 4-hydroxypyrazolo [3,4-d] pyrimidine and its riboside, respectively, under the similar conditions.5-Amino-1-β-D-ribofuranosyipyrazole-4-carboxamide and 5-amino-1-β-D-ribofuranosyl- pyrazole-4-carboxamide 5′-phosphate are new compounds. 相似文献
2.
Jack D. Anderson Roland K. Robins Ganapathi R. Revankar 《Nucleosides, nucleotides & nucleic acids》2013,32(5):853-863
Abstract The synthesis of pyrazolo[3,4-d]pyrimidine ribonucleoside 3′, 5′-cyclic phosphates related to cAMP, cIMP and cGMP has been achieved for the first time. Phosphorylation of 4-amino-6-methylthio-1-β-D-ribo-furanosylpyrazolo[3,4-d]pyrimidine (1) with POCl3 in trimethyl phosphate gave the corresponding 5′-phosphate (2a). DCC mediated intramolecular cyclization of 2a gave the corresponding 3′, 5′-cyclic phosphate (3a), which on subsequent dethiation provided the cAMP analog 4-amino-1-β-D-ribofuranosylpyrazolo[3, 4-d]pyrimidine 3′, 5′-cyclic phosphate (3b). A similar phosphorylation of 6-methylthio-1-β-D-ribofuranosylpyrazolo[3, 4-d]pyrimidin-4(5H)-one (5), followed by cyclization with DCC gave the 3′, 5′-cyclic phosphate of 5 (9a). Dethiation of 9a with Raney nickel gave the cIMP analog 1-β-D-ribofuranosylpyrazolo[3, 4-d]pyrimidin-4(5H)-one 3′, 5′-cyclic phosphate (9b). Oxidation of 9a with m-chloroperoxy benzoic acid, followed by ammonolysis provided the cGMP analog 6-amino-1-β-D-ribofuranosylpyrazolo [3, 4-d] pyrimidin-4(5H)-one 3′, 5′-cyclic phosphate (7). The structural assignment of these cyclic nucleotides was made by UV and H NMR spectroscopic studies. 相似文献
3.
Akira K. Tanaka Akio Kobayashi Kyohei Yamashita 《Bioscience, biotechnology, and biochemistry》2013,77(12):2537-2542
1-O-Palmitoyl-d-glucopyranose was prepared by the selective 1-O-acylation of 4,6-O-benzylideneglucose followed by hydrogenolysis of the protecting group. 1-O-Oleoyl-d-glucopyranose was synthesized from the corresponding benzylidene derivative by selective hydrolysis in acetic acid. This procedure constitutes a useful method for the synthesis of 1-O-acyl-d-glucopyranoses containing unsaturated carboxylic acids. However, 4,6-O-benzylidene-l-O-linolenoyl-d-glucopyranose was converted to 3-O-linolenoyl-d-glucopyranose by the acidic hydrolysis due to acyl migration.Synthesized glucosyl esters were inactive in the bean second-internode bioassay. However, it was found that 3-O-linolenoyl-d-glucopyranose had a promoting activity on germination of pollen and growth of pollen tube. 相似文献
4.
Synthesis of 9-β-d-glucopyranosyl-adenine-6′-phosphate is described. The method developed here involves the process of condensation of base (chloromercuri-6-benzamidopurine) (I) with phosphorylated sugar (2,3,4-tri-O-acetyl-6-diphenylphosphoryl-α-d-glucopyranosyl bromide) (II). This reaction gives crystalline 6-benzamido-9-(2′,3′,4′-tri-O-acetyl-6′-diphenylphosphoryl-β-d-glucopyranosyl)-purine (III) in high yield, which is converted to the desired nucleotide by alkaline hydrolysis. 相似文献
5.
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
6.
Harukazu Fukami Shoji Ikeda Hideki Kohno Minoru Nakajima 《Bioscience, biotechnology, and biochemistry》2013,77(12):2383-2388
Methyl 2,5-di-O-p-nitrobenzoyl-β-d-ribofuranoside was prepared via methyl 2,3-O-ethoxyethylidene-β-d-ribofuranoside from d-ribose. It was condensed with 3,4,6-tri-O-acetyl-2-deoxy-2-(2′,4′-dinitroanilino)-α-d-glucopyranosyl bromide and 3,4-di-O-acetyl-2,6-dideoxy-2-(2′,4′-dinitroanilino)-6-phthalimido-α-d-glucopyranosyl bromide by a modified Königs-Knorr reaction to give neobiosamine analogs. The condensation reaction gave α-glucosides as the minor product, and the corresponding β-glucoside as the major product. 相似文献
7.
Tohru Kodama Hidekatsu Ishida Tetsuro Kokubo Takashi Yamakawa Hiroshi Noguchi 《Bioscience, biotechnology, and biochemistry》2013,77(12):3283-3288
A cell suspension culture of a Vitis hybrid converted quercetin to six glucosides. Their structures were identified as quercetin 3-O-β-d-glucopyranoside, quercetin 3,4′-di-O-β-d-glucopyranoside, quercetin 3,7-di-O-β-d-glucopyranoside, isorhamnetin 3-O-β-d-glucopyranoside, isorhamnetin 3,4′-di-O-β-d-glucopyranoside, and isorhamnetin 3,7-di-O-β-d-glucopyranoside by UV, FD-MS, 1H-NMR, 13C-NMR spectroscopy and TLC analysis.The course of conversion was also investigated and it was shown that quercetin 3-O-glucoside reached the maximum yield of 31% in 24 hr and then gradually disappeared accompanied by the production of quercetin 3,4′- and 3,7-di-O-glucosides. Although the same rise and fall relationship was observed between isorhamnetin 3-O-glucoside and isorhamnetin 3,4′- or 3,7-di-O-glucoside, their conversion ratios were much lower than those of quercetin glucosides. 相似文献
8.
Susumu Ikegami Yutaka Hirose Yuji Kamiya Saburo Tamura 《Bioscience, biotechnology, and biochemistry》2013,77(13):2453-2457
Partial acid hydrolysis of asterosaponin A, a steroidal saponin, afforded two new disaccharides in addition to O-(6-deoxy-α-d-glucopyranosyl)-(l→4)-6-deoxy-d-glucose which has been characterized in the preceding paper. The formers were demonstrated as O-(6-deoxy-α-d-galactopyranosyl)-(1→4)-6-deoxy-d-glucose and O-(6-deoxy-α-d-galactopyranosyl)-(l→4)-6-deoxy-d-galactose, respectively.Accordingly, the structure of carbohydrate moiety being composed of two moles each of 6-deoxy-d-galactose and 6-deoxy-d-glucose, was established as O-(6-deoxy-α-d-galactopyranosyl)-(l→4)-O-(6-deoxy-α-d-galactopyranosyl)-(l→4)-O-(6-deoxy-α-d-glucopyranosyl)-(l→4)-6-deoxy-d-glucose, which is attached to the steroidal aglycone through an O-acetal glycosidic linkage. 相似文献
9.
A new procedure which involves 1-trichloroacetyl sugars as the starting material has been developed for the synthesis of purine nucleosides. 7-β-d-Glucopyranosyl-, 7-β-d-xylopyranosyl-, 7-β-d-ribopyranosyl-theophylline, 9-(tetra-O-acetyl-β-d-glucopyranosyl)-2,6,8-trichloropurine and 9-β-d-glucopyranosyl adenine were prepared in good yields by the reaction in fusion of purine bases with 1-trichloroacetyl sugars, using zinc chloride, p-toluenesulfonic acid, or ethyl polyphosphate as catalyst. 9-d-Ribofuranosyl adenine was also prepared by the same procedures, although the anomeric configuration of the compound is not yet definite. The effect of catalysts on the yields of purine nucleosides is discussed. 相似文献
10.
Donald E. Bergstrom Peiming Zhang W. Travis Johnson 《Nucleosides, nucleotides & nucleic acids》2013,32(1-3):59-68
Abstract A series of heterocyclic carboxamides have been designed as mimics for the natural nucleic acid bases. The nucleosides 1-(2′-deoxy-β-d-ribofuranosyl)imidazole-4-carboxamide (1), 1-(2′ -deoxy-β-d-ribofuranosyl)pyrazole-3-carboxamide (2), and 1-(2′ -deoxy-β-d-ribofuranosyl)pyrrole-3-carboxamide (3) were synthesized and their structures confirmed by spectroscopic and analytical means. 相似文献
11.
The electrophoretically homogeneous glucomannan isolated from konjac flour was composed of d-glucose and d-mannose residues in the approximate ratio of 1: 1.6. Controlled acid hydrolysis gave 4-O-β-d-mannopyranosyl-d-mannose, 4-O-β-d-mannopyranosyl-d-glucoseT 4-O-β-d-glucopyranosyl-d-glucose(cellobiose), 4-O-β-d-glucopyranosyl-d-mannose(epicellobiose), O-β-d-mannopyranosyl-(1→4)-O-β-d-mannopyranosyl-(1→4)-d-mannose, O-β-d-glucopyranosyl- (1→4)-O-β-d-mannopyranosyl-(1→4)-d-mannose, O-β-d-mannopyranosyl-(1→4)-O-β-d-glucopy- ranosyl-(1→4)-d-mannose and O-β-d-glucopyranosyl-(1→4)-O-β-d-glucopyranosyl-(1→4)-d-mannose. 相似文献
12.
Teruo Amachi Shoji Imamoto Hajime Yoshizumi 《Bioscience, biotechnology, and biochemistry》2013,77(8):1222-1230
A growth factor (TJF) for a malo-lactic fermentation bacterium has been isolated from tomato juice, and found to be a β-glucoside. The NMR spectra of TJF and its acetate revealed that the glucosyl residue linked to the hydroxyl group at C-2′ or C-4′ of d- or l-pantothenic acid moiety. Then, 2′-O-(β-d-glucopyranosyl)-dl-pantothenic acid (I), 4′-O-(β-d-glucopyranosyl)-dl-pantothenic acid (II) and 4′-O-(β-d-glucopyranosyl)-d(R)-pantothenic acid (II-a) were synthesized, and Il-a and 4′-O-(β-d-glucopyranosyl)-l-pantothenic acid (II-b) were obtained by the optical resolution of the acetate of II. Among the above compounds, II-a was identical with natural TJF regarding to the biological activity, NMR and ORD spectra, and thin-layer chromatography. 相似文献
13.
A pectin isolated from tobacco midrib contained residues of d-galacturonic acid (83.7%), L-rhamnose (2.2%), l-arabinose (2.4%) and d-galactose (11.2%) and small amounts of d-xylose and d-glucose. Methylation analysis of the pectin gave 2, 3, 5-tri- and 2, 3-di-O-methyl-l-arabinose, 3, 4-di- and 3-O-methyl-l-rhamnose and 2, 3, 6-tri-O-methyl-d-galactose. Reduction with lithium aluminum hydride of the permethylated pectin gave mainly 2, 3-di-O-methyl-d-galactose and the above methylated sugars. Partial acid hydrolysis gave homologous series of β-(1 → 4)-linked oligosaccharides up to pentaose of d-galactopyranosyl residues, and 2-O-(α-d-galactopyranosyluronic acid)-l-rhamnose, and di- and tri-saccharides of α-(1 → 4)-linked d-galactopyranosyluronic acid residues.These results suggest that the tobacco pectin has a backbone consisting of α-(1 → 4)-linked d-galactopyranosyluronic acid residues which is interspersed with 2-linked l-rhamnopyranosyl residues. Some of the l-rhamnopyranosyl residues carry substituents on C-4. The pectin has long chain moieties of β-(1 → 4)-linked d-galactopyranosy] residues. 相似文献
14.
《Bioscience, biotechnology, and biochemistry》2013,77(3):560-565
Partial acid hydrolysis of Saccharomyces cerevisiae mannan gave 2-O-α-d-Manp-d-Man (1), 3-O-α-d-Manp-d-Man (2), 6-O-α-d-Manp-d-Man (3), O-α-d Manp-(1→2)O-α-d-Manp-(1→2)-d-Man (4), O-α-d-Manp-(1→2)-O-α-d-Manp-(1→6)-d-Man (5), O-α-d Manp-(1→6)-6-O-α-d-Manp-(1→6)-d-Man (6), O-α-d Manp-(1→2)-O-α-d-Manp-(1→2)-6-O-α-d-Manp-(1→6)-d-Man (7), O-α-d-Manp-(1→2)-O-α-d-Manp-(1→6)-O-α-d-Manp-(1→6)-d-Man (8), and O-α-d-Manp-(1→6)-O-[α-d-Manp-(1→2)]-O-α-d-Manp-(1→6)-d-Man (9). 相似文献
15.
Acremonium sp. 15 a fungus isolated from soil, produces an extracellular enzyme system degrading cyclic (1→2)-β-d-glucan. This enzyme was found to be a mixture of endo-(1→2)-β-d-glucanase and β-d-glucosidase. The (1→2)-β-d-glucanase was purified to homogeneity shown by disc-electrophoresis after SP-Sephadex column chromatography, Sephadex G-75 gel filtration, and rechromatography on SP-Sephadex. The molecular weight of the enzyme was 3.6 × 104 by SDS-polyacrylamide gel electrophoresis. The isoelectric point of the enzyme was pH 9.6. The enzyme was most active at pH 4.0—4.5, and stable up to 40°C in 20 mm acetate buffer (pH 5.0) for 2 hr of incubation. This enzyme hydrolyzed only (l→2)-β-d-glucan and did not hydrolyze laminaran, curdlan, or CM-cellulose. The hydrolysis products from cyclic (1→2)-β-d-glucan were mainly sophorose.The β-d-glucosidase was purified about 4000-fold. The rate of hydrolysis of the substrates by this β-d-glucosidase decreased in the following order: β-nitrophenyl-β-d-glucoside, sophorose, phenyl-β-d-glucoside, laminaribiose, and salicin. This enzyme has strong transfer action even at the low concentration of 0.75 mm substrate. 相似文献
16.
Kikue Kubota Akio Kobayashi Tei Yamanishi 《Bioscience, biotechnology, and biochemistry》2013,77(11):2753-2754
Quinoxaline and benzimidazole derivatives obtained from L-rhamnose and L-fucose under deoxygenated, weakly acidic, heated conditions were studied using GLC, HPLC, and NMR.Four quinoxalines and one benzimidazole were obtained from L-rhamnose (RHA-I, II, III, III′, and IV) and L-fucose (FUA-I, II, III, IV, and V) in an acidic solution (MeOH-AcOH-H2I = 8 : 1 : 2) at 80°C. The total yield of the products as sugar was about 80% from either rhamnose or fucose.The structure of RHA-I was (2′S)-2-methyl-3-(2′-hydroxypropyl)quinoxaline; RHA-II, (2′R,3′S)-2-(2′,3′-dihydroxybutyl)quinoxaline; RHA-III, (1′S,2′S,3′S)-2-(1′2′3′-trihydroxybutyl)quinoxaline[2-(L-arabino-1′,2′,3′-trihydroxybutyl)quinoxaline]; RHA-III′, 2-(L-ribo-1′,2′,3′-trihydroxybutyl)quinoxaline; and RHA-IV, 2-(L-manno-1′,2′,3′,4′-tetrahydroxypentyl)-benzimidazole, and the structure of FUA-I was the same as RHA-I; FUA-II, (2′S, 3′S)-2-(2′, 3′-dihydroxybutyl)quinoxaline; FUA-III, (1′R, 2′R, 3′S)-2-(1′,2′,3′-trihydroxybutyl)quinoxaline [2-(L-xylo-1′,2′,3′-trihydroxybutyl)quinoxaline; FUA-IV, 2-(L-lyxo-1′,2′,3′-trihydroxybutyl)-quinoxaline; and FUA-V, 2-(L-galacto-1′,2′,3′,4′-tetrahydroxypentyl)benzimidazole. These results suggest no significant difference for the pathways of quinoxaline and benzimidazole formation between L-rhamnose and L-fucose. Possible pathways are proposed for each sugar. 相似文献
17.
Nozomi Hiura Isao Honjyo Tasuku Nakajima Kazuo Matsuda 《Bioscience, biotechnology, and biochemistry》2013,77(4):1041-1047
The chemical structure of cell wall β-d-glucans as well as the activities of lytic enzymes such as β-1,3-d-glucanase and β-1,6-d-glucanase changed during the growth of Neurospora crassa.A dramatic change in the cell wall β-d-glucan structure was observed between cells of the middle logarithmic phase and ones of the late logarithmic phase. The ratio of 1,3-linked glucose residues to non reducing terminal glucose residues decreased from 85 to 55 and the ratio of gentiobiose as a hydrolysis product with exo-β-1,3-d-glucanase increased significantly between the two phases.Two prominent peaks of β-1,3-d-glucanase as well as the β-1,6-d-glucanase activities appeared in the culture filtrate at different growth stages, the early logarithmic phase and the stationary phase. In the cell wall, β-d-glucosidase activity instead of the β-l,6-d-glucanase and β-1,3-d-glucanase activities was observed in the late logarithmic phase. 相似文献
18.
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
19.
Hideo Fukui Minoru Tanaka Akira Misaki 《Bioscience, biotechnology, and biochemistry》2013,77(8):2343-2349
The structure of an acidic polysaccharide elaborated by Bacillus polymyxa S-4 was investigated in relation to its physiological activity, particularly, its hypocholesterolemic effect on experimental animals. The polysaccharide is composed of d-glucose, d-mannose, d-galactose, d-glucuronic acid, and d-mannuronic acid (molar ratio 3:3:1: 2:1). Methylation and fragmentation analyses, such as Smith degradation and partial acid hydrolysis showed that the polysaccharide has a complicated, highly branched structure, consisting mainly of (1 → 3)- and (1 → 4)-d-glycosidic linkages. The backbone chain containing d-glucuronic acid, d-mannose, and d-galactose residues is attached at the C-3, C-4, and C-4 positions, respectively, with side chains of single or a few carbohydrate units, which are terminated with d-glucose or d-mannose residues. 相似文献
20.
Mariko Uziie Masaru Matsuo Tsuneo Yasui 《Bioscience, biotechnology, and biochemistry》2013,77(4):1167-1173
The nature of the active site of Chaetomium trilaterale β-xylosidase catalyzing the hydrolysis of β-d-glucopyranoside and β-d-xylopyranoside was investigated by kinetic methods. On experiments with mixed substrates, such as phenyl β-d-xylopyranoside and phenyl β-d-glucopyranoside, the kinetic features agreed very closely with those features theoretically predicted for a single active site of the same enzyme catalyzing the hydrolysis of these two kinds of substrates.Both the β-glucosidase and β-xylosidase activities were strongly inhibited by glucono-1,5-lactone and nojirimycin (5-amino-5-deoxy-d-glucopyranose). β-Xylosidase activity was inhibited non-competitively by the two inhibitors, but β-glucosidase activity was competitive. Methyl β-d-xylopyranoside, methyl β-d-glucopyranoside, 1-thiophenyl β-d-xylopyranoside, and 1-thiophenyl β-d-glucopyranoside poorly inhibited both activities. Methyl β-d-xylopyranoside inhibited the β-xylosidase activity competitively but the β-glucosidase activity was non-competitive, whereas methyl β-d-glucopyranoside inhibited the β-xylosidase activity non-competitively but the β-glucosidase activity was competitive. 1-Thiophenyl β-d-xylopyranoside and 1-thiophenyl β-d-glucopyranoside behaved as competitive inhibitors.From these results, it was concluded that the β-xylosidase and β-glucosidase activities reside in one catalytic site, and this suggests that there might be two kinetically distinct binding sites in the active center of the same enzyme. 相似文献