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1.
Daikichi Nishimura Akira Hasegawa Minoru Nakajima 《Bioscience, biotechnology, and biochemistry》2013,77(10):1767-1772
The condensation reaction of 3-acetamido-2,4,6-tri-O-benzyl-3-deoxy-α-d-glucopyranosyl chloride, 6-acetamido-2,3,4-tri-O-benzyl-6-deoxy-d-glucopyranosyl chloride and 2,3,4,6-tetra-O-benzyl-α-d-glucopyranosyl chloride were performed by a modified Königs-Knorr method. The rapid conversion of the benzyl halogeno derivative of 3-acetamido-3-deoxy-d-glucose to a stable intermediate caused a poor yield in the glucoside formation with complex aglycons at the presence of dioxane. For the benzyl halogeno derivative of 6-acetamido-6-deoxy-d-glucose, the C-6 acetamido group was favorable to the α-glucoside formation by its anchimeric assistance. A favorable effect of dioxane was observed for the α-glucoside formation of benzyl halogeno derivative of d-glucose. 相似文献
2.
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
3.
Hisao Shibata Daikichi Nishimura Norio Kurihara Minoru Nakajima 《Bioscience, biotechnology, and biochemistry》2013,77(8):1002-1005
From 2,3,4,6-tetra-O-benzoyl-α-d-mannopyranosyl bromide by the Königs-Knorr reaction, α-d-mannos ides of (+)- and (?)-N-carbobenzoxy-trans-2-amino-cyclohexanol and 3-bromo-3-deoxy-1,2;4,5-di-O-isopropylidene-muco-inositol were synthesized. 相似文献
4.
Yo Kikuchi Yoshiyuki Sakano Ryo Taguchi Tsuneo Kobayashi 《Bioscience, biotechnology, and biochemistry》2013,77(5):1091-1092
3,4-Di-O-acetyl-2,6-dideoxy-2-(2′,4′-dinitroanilino)-6-phthalimido-α-d-glucopyranosyl bromide (I) was prepared in a good yield from glucosamine hydrochloride. A modified Königs-Knorr condensation of this bromide with a 2-deoxysteptamine derivative afforded a neamine derivative (IX) and its diastereomer (X). These compounds, (IX) and (X), were identified by PMR spectroscopy after conversion into the corresponding N-acetyl derivatives, (XI) and (XII). 相似文献
5.
Kazuo Matsumoto Tsuyomi Miyahara Mamoru Suzuki Muneji Miyoshi 《Bioscience, biotechnology, and biochemistry》2013,77(5):1097-1099
The 5-O-(2,6-diamino-2,6-dideoxy-α-d-glucopyranosyl)-2-deoxystreptamine derivative and its related compounds were synthesized by a modified Königs-Knorr condensation of 3,4-di-O-acetyl-2,6-dideoxy-2-(2′,4′-dinitroanilino)-6-phthalimido-α-d-glucopyranosyl bromide (I) with 4,6-di-O-acetyl-N,N′-dicarbobenzoxy-2-deoxystreptamine (V) and the corresponding streptamine (XI). The aglycons (V) and (XI) were prepared by selective acetylation of the aminocyclitol derivatives by taking advantage of the reactivity difference between the hydroxyl groups at C5 and C4 or C6. The condensed products were converted to N-acetyl derivatives and were shown to have the α-configuration by PMR spectroscopy. 相似文献
6.
Shintaro Kamiya Sachiko Esaki Misao Hama 《Bioscience, biotechnology, and biochemistry》2013,77(4):397-409
In order to investigate the substrate-specificity of α-l-rhamnosidase induced in Aspergillus species, the titled compounds were synthesized employing the various kinds of methods.One is the Helferich reaction by using the sirupy l-rhamnose teteraacetate and appropriate phenols in the presence of p-toluenesulphonic acid or zinc chloride etc. The other method is Königs-Knorr reaction by using triacetyl α-l-rhamnosyl bromide and appropriate phenols in the presence of mercuric salts. The excellent result was obtained by the former method than the latter one. Deacetylation of the resulting esters (MeOH-NaOMe) gave the titled compounds.Naturally occurring flavanone-7-neohesperidoside, naringin and neohesperidin contained in citrus peels were synthesized. β-Neohesperidose heptaacetate was treated with hydrogen bromide in acetic acid, giving hexaacetyl α-neohesperidosyl bromide. The latter compound coupled with phloroacetophenone in the presence of silver carbonate in quinoline yielded phloroacetophenone-4-neohesperidoside after deacetylation.Condensation of phloroacetophenone-4-neohesperidoside with p-hydroxybenzaldehyde and isovanilline respectively in the presence of strong alkali afforded the corresponding chalcone-neohesperidosides, which were converted by ring closure to naringin and neohesperidin respectively.Furthermore, the reactivity among phloroacetophenone-4-glycosides, namely β-d-gluco-side, β-d-xyloside, and β-neohesperidoside and fifteen kinds of substituted benzaldehydes was investigated. Phloroacetophenone-4-β-d-glucoside reacted with p-hydroxybenzaldehyde, p-anisaldehyde isovanillin and protocatechualdehyde. In the case of phloroacetophenone-4-β-d-xyloside the same result was obtained except the case of protocatechualdehyde.In the case of phloroacetophenone-4-neohesperidoside reacted only with p-hydroxybenzaldehyde and isovanillin. 相似文献
7.
Akira Hasegawa Daikichi Nishimura Takashi Kurokawa Minoru Nakajima 《Bioscience, biotechnology, and biochemistry》2013,77(10):1773-1776
Paromamine and its related compounds were synthesized by a modified Königs-Knorr reaction of 3,4,6-tri-O-acetyl-2-(2′,4′-dinitroanilno)-α-d-glucopyranosyl bromide with isopropylidene derivatives of 2-deoxystreptamine, streptamine and dihydroconduramine F–4. The condensed products were isolated as their poly N-acetyl derivatives and proved to have α-configuration by PMR spectroscopy in D2O. 相似文献
8.
Benzyl 2, 3, 6-tri-O-acetyl-4-O-(2,3-di-O-acetyl-4,6-di-O-methylsulfonyl-β-d-glucopyranosyl)-β-d-glucopyranoside (VI) was prepared from α-cellobiose octaacetate. Displacement of the sulfonyl esters of VI with acyloxy-groups in N, N-dimethyl formamide in the presence of sodium benzoate gave 4-O-β-d-galactopyranosyl-d-glucopyranose derivative (lactose derivative). Elimination of blocking groups of the derivative yielded lactose hydrate (IX), though the overall yield of lactose from cellobiose octaacetate was less than 2%. 相似文献
9.
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
10.
Nobuyuki Sato Kousaku Murata Akira Kimura 《Bioscience, biotechnology, and biochemistry》2013,77(4):1057-1059
N-Acetyl-6-O-phosphono-muramoyl-l-alanyl-d-isoglutamine methyl ester and a variety of its 1-α-O-acyl derivatives were synthesized from benzyl 2-acetamido-2-deoxy-3-O-[d-1-(methoxycar-bonyl)ethyl]-β-d-glucopyranoside. Their immunoadjuvant activity in guinea-pigs was examined. 相似文献
11.
《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
12.
Fumio Yagi Kenjiro Tadera Akira Kobayashi 《Bioscience, biotechnology, and biochemistry》2013,77(10):2985-2990
transglucosylation by a β-d-glucosidase from cycad seeds. These azoxyglycosides, named neocycasin H, I, and J, were identified as O-β-d-glucopyranosyl-(1→4)-O-β-d-glucopyranosyl-(l→3)-O-β-d-glucopyranoside of methylazoxymethanol (MAM), O-β-d-glucopyranosyl-(1→3)-[O-β-d-glucopyranosyl-(1→6)]-O-β-d-glucopyranoside of MAM, and O-β-d-glucopyranosyl-(1→3)-[O-β-d-xylopyranosyl-(1→6)]-O-β-d-glucopyranoside of MAM, respectively. On the basis of their structures, the mechanism of the formation of these neocycasins is also discussed. 相似文献
13.
Tateo Suzuki Shin’ichi Matsui Katura Tuzimura 《Bioscience, biotechnology, and biochemistry》2013,77(6):1061-1063
One of the bound forms of vitamin B6 occurring in rice bran was isolated in a faintly yellowish syrup by repeating ion-exchange and paper-partition chromatographic techniques. The behaviors of the isolate on thin-layer and Aminex A–5 column chromatograms were coincident with those of synthetic pyridoxine-β-d-glucoside which was obtained by Königs-Knorr condensation of α4,3-O-isopropylidene pyridoxine and 2,3,4,6-tetra-O-acetyl-α-d-glucopyranosyl bromide. On acid hydrolysis, the isolate gave pyridoxine and glucose. Glucose was proved to bind to the 5-hydroxymethyl group of pyridoxine, because the isolate did not react with 2,6-dichloroquinone chlorimide in the presence of boric acid. An equimolar amount of pyridoxine and d-glucose was produced with an equivalent consumption of the isolate by the action of β-glucosidase. No essential difference between the isolated and synthetic preparations could be detected in UV- and NMR-spectral features. Thus, the chemical structure of the isolate was identified as 5′-O-(β-d-glucopyranosyl) pyridoxine. 相似文献
14.
Synthesis of Some New α- and β-(l→2) Linked Disaccharides Containing L-Quinovose (6-Deoxy L-Glucose)
Shintaro Kamiya Sachiko Esaki Fukuko Konishi 《Bioscience, biotechnology, and biochemistry》2013,77(2):273-276
Hepta-O-acetyl-2-0-β-l-quinovopyranosyl-α-d-glucose (VI) and hepta-O-acetyl-2-O-α-l-quinovopyranosyl-β-d-gIucose (VIII) were prepared by the coupling of 2,3,4-tri-O-acetyl-α-l-quinovopyranosyl bromide (IV) with l,3,4,6-tetra-O-acetyl-α-D-glucose (V) in the presence of mercuric cyanide and mercuric bromide in absolute acetonitrile.Similarly, hepta-O-acetyW-O-α-l-quinovopyranosyl-α-d-galactose (X) and hepta-O-acetyl-2-O-β-L-quinovopyranosyl-α-d-galactose (XI) were prepared by the reaction of IV with 1,3,4,6-tetra-O-acetyl-α-d-galactose (IX).Removal of the protecting groups of VI, VIII, X and XI afforded the corresponding disaccharides. On treatment with hydrogen bromide, VI, VIII, X and XI gave the corresponding acetobromo derivatives. 相似文献
15.
Shôji Mizushima Kazuo Izaki Hajime Takahashi Kin-ichiro Sakaguchi 《Bioscience, biotechnology, and biochemistry》2013,77(4):178-182
The fractional determination of d-glutamic and d-aspartic acids using the enzyme preparation of Aspergillus ustus strain f. was studied. In the first part of this paper, the procedure of enzyme preparation, the effect of sodium chloride on enzyme activity, and a new device for the fractional determination of d-glutamic and d-aspartic acids are described. In the latter part, the contents of d-glutamic and d-aspartic acids of cancer and normal tissues are estimated. However, it was found that the cancer tissues are not characterized by the presence of d-glutamic acid in opposition to Kögl’s claim. 相似文献
16.
Koya Kawano Kazuki Sakai Hiroji Sato Sadao Sakamura 《Bioscience, biotechnology, and biochemistry》2013,77(10):1999-2002
During an examination of components contributing to the bitter taste of asparagus bottom cut (Asparagus officinalis L.), two new furostanol saponins were isolated from roots extractives. Their chemical structures were established as 5β-furostane-3β,22,26 triol-3-O-β-d-glucopyranosyl (1→2)-β-d-glucopyranoside 26-O-β-d-glucopyranoside and 5β-furostane-3β,22,26 triol-3-O-β-d-glucopyranosyl (1→2) [β-d-xylopyranoxyl (1→4)]-β-d-glucopyranoside 26-O-β-d-glucopyranoside respectively. 相似文献
17.
Keiji Yano Naoki Higashi Satoshi Nakamura Kei Arima 《Bioscience, biotechnology, and biochemistry》2013,77(9):1363-1365
The transglucosidation reaction of brewer’s yeast α-glucosidase was examined under the co-existence of l-sorbose and phenyl-α-glucoside. As the transglucosidation products, three kinds of new disaccharide were chromatographically isolated. It was presumed that these disaccharides consisting of d-glucose and l-sorbose were 1-O-α-d-glucopyranosyl-l-sorbose ([α]D+89.0), 3-O-α-d-glucopyranosyl-l-sorbose ([α]D+69.1) and 4-O-α-d-glucopyranosyl-l-sorbose ([α]D+81.0). The principal product formed in the enzyme reaction was 1-O-α-d-glucopyranosyl-l-sorbose. 相似文献
18.
During the investigations on riboflavin glycoside formation by Aspergillus, Mucor, Penicillium and Rhizopus, a remarkable production of 5′-d-riboflavin-α-d-glucopyranoside was observed in several strains belonging to the genus Mucor when grown on a, medium containing maltose and riboflavin. Several conditions on 5′-d-riboflavin-α-d-glucopyranoside formation were also investigated with washed mycellium of M. javanicus. Maltosyl compounds such as maltose, dextrin, amylose and soluble starch were the effective glucosyl donor, whereas glucose, fructose, sucrose, lactose and dextran were inactive. 相似文献
19.
Hiroshi Ogawa Teiichiro Ito Shinichi Kondo Shigeharu Inoue 《Bioscience, biotechnology, and biochemistry》2013,77(4):289-310
The antibiotic kanamycin was degraded with methanolic hydrogen chloride and was determined to be composed of three compounds: deoxystreptamine, 6-amino-6-deoxy-d-glucopyranose and 3-amino-3-deoxy-d-glucopyranose. From the chemical and physical data on the antibiotic and its fragments, kanamycin was shown to be O-α-6-amino-6-deoxy-d-glucopyranosyl-(1→4 or 6)-O-[α-3-amino-3-deoxy-d-glucopyranosyl-(1→6 or 4)]-1,3-diamino-1, 2, 3-trideoxy-myo-inositol. 相似文献
20.
Ryutaro Utsumi 《Bioscience, biotechnology, and biochemistry》2013,77(8):2129-2130
The substrate specificity of α-d-xylosidase from Bacillus sp. No. 693–1 was further investigated. The enzyme hydrolyzed α-1,2-, α-1,3-, and α-1,4-xylobioses. It also acted on some heterooligosaccharides such as O-α-d-xylopyranosyl-(1→6)-d-glucopyranose, O-α-d-xylopyranosyl-(1→6)-O-β-d-glucopyranosyl-(1→4)-d-glucopyranose, O-α- d-xylopyranosyl-(1→6)-O-d-glucopyranosyl-(1→4)-O-[α-d-xylopyranosyl-(1→6)]-d-glucopyranose, and O-α-d-xylopyranosyl-(1→3)-l-arabinopyranose. The enzyme was unable to hydrolyze tamarinde polysaccharides although it could hydrolyze low molecular weight substrates with similar linkages. 相似文献