Eine praktikable Synthese von <i>N</i>‐Acetyl‐<scp>D</scp>‐lactosamin mit Galactose‐Oxidase und β‐Galactosidase

Kimura, Teiji; Takayama, Shuichi; Huang, Hongmei; Wong, Chi‐Huey

doi:10.1002/ange.19961082010

Cited by 4 publications

(4 citation statements)

References 38 publications

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“…Concerning the β-galactosidase from Bacillus circulans different saccharides were recognized as acceptor molecules, however so far, there were only two derivatised galactosides published as donor molecules for the β-galactosidase from Bacillus circulans. [23,25,26] These results indicate that the primary alcohol function does not seem to be essential for recognition by the enzyme.…”

Section: β-Galactosidase Catalysed Glycosylationmentioning

confidence: 80%

“…Again, 4-nitrophenyl 6-O-allyl-β--galactopyranoside (12) was not recognized. Reaction of the C-6 oxidized donor 4-nitrophenyl β--galacto-hexodialdopyranoside [23] (6) could be confirmed, and the disacccharide allyl β--galacto-hexodialdopyranosyl-(1Ǟ4)-2-acetamido-2-deoxy-α--glucopyranoside (22) was isolated in 68 % yield. Further reactions employing the donors pNP-Fuc (16) and pNP-Ara (17) led to disaccharides 19 (66 %) and 24 (76 %) as well as 20 (6 %) and 25 (13 %), (Scheme 2) indicating excellent substrate properties of the 6-deoxy--galacto derivative in contrast to the -arabino derivative.…”

Section: β-Galactosidase Catalysed Glycosylationmentioning

confidence: 94%

“…A much more efficient synthesis of aldehyde 6 could be performed by selective oxidation of pNP β--galactopyranoside (1). Best yields were obtained by galactose oxidase catalysed oxidation, [23] which gave the product 6 in nearly quantitative yield.…”

Section: Synthesis Of Modified Galactosyl Donorsmentioning

confidence: 99%

“…[28][29][30] For initial studies the easily accessible diisopropylidene aldehydo galactose 26 [19,31] was chosen. As 2-amino sugars the glucoamine derivatives 27 [32] and 28, obtained from 15 using a method according to Wong et al, [23] as well as the 2-amino-1,5-anhydro-glucitol 29 were selected. The linkage formation was easily done with sodium cyanoborohydride in aqueous methanol at pH 6 and room temperature.…”

Section: Reductive Aminationmentioning

confidence: 99%

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Synthesis of Novel Di‐ and Trisaccharide Mimetics with Non‐Glycosidic Amino Bridges

2007

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Synthesis of novel di‐ and trisaccharides using enzymatic glycosylation, Dess–Martin oxidation and reductive amination allows rapid access to the target structures. Thus, a novel class of glycomimetics was obtained having nitrogen inserted as bridging atom between two non‐anomeric positions. Novel di‐ and trisaccharide mimetics were designed using N‐acetylglucosamine as a basis structure. A third monosaccharide unit was attached via an unnatural sugar–sugar bond without participation of the anomeric center. Their synthesis, proceeding via oxidation, glycosylation and reductive amination, required only a few steps, thus allowing rapid access to the target structures. Generation of the novel pseudo‐disaccharide was achieved by Dess–Martin oxidation and a subsequent reductive amination. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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Section: β-Galactosidase Catalysed Glycosylationmentioning

confidence: 80%

Section: β-Galactosidase Catalysed Glycosylationmentioning

confidence: 94%

Section: Synthesis Of Modified Galactosyl Donorsmentioning

confidence: 99%

Section: Reductive Aminationmentioning

confidence: 99%

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Synthesis of Novel Di‐ and Trisaccharide Mimetics with Non‐Glycosidic Amino Bridges

2007

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Die Heyns-Umlagerung in neuem Licht: außergewöhnlich einfache Synthese vonD-Lactosamin aus Lactulose

Wrodnigg¹,

Stütz²

1999

Angewandte Chemie

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Disaccharide mit D‐Glucosamin am reduzierenden Ende lassen sich elegant und in guten Ausbeuten durch die Titelreaktion aus O‐glycosylierten D‐Fructosen herstellen [Gl. (a)]. Die Methode verlief mit allen untersuchten Disacchariden – vermutlich wegen der ausgeprägten destabilisierenden Wechselwirkungen der Glycosylreste an O‐4 mit den übrigen polaren Gruppen – deutlich effizienter als mit der unsubstituierten D‐Fructose, deren Reaktion mit Ammoniak zu D‐Glucosamin in den fünfziger Jahren von Heyns und Koch beschrieben wurde.

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ChemInform Abstract: A Practical Method for the Synthesis of N‐Acetyl‐D‐lactosamine Derivatives by the Tandem Use of Galactose Oxidase and β‐ Galactosidase.

et al. 1997

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A Practical Method for the Synthesis of N-Acetyl-D-lactosamine Derivatives by the Tandem Use of Galactose Oxidase and β-Galactosidase.-The title compounds are useful for the study of biological recognition processes. Syntheses of them by chemical methods are known but often involve many steps and are complicated; enzymatic methods are expensive or -if β-D-galactose from Bacillus circulans is used -give low yields and make it difficult to isolate the desired products. In this work is reported that (I) via intermediate oxidation of the primary OH group to an aldehyde with galactose oxidase can be used as a donor in the transglycosylation catalyzed by β-galactosidase leading to the desired disaccharide (V) in good yield and with high stereoselectivity. -(KIMURA, T.; TAKAYAMA, S.; HUANG, H.; WONG, C.-H.; Angew.

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Eine praktikable Synthese von N‐Acetyl‐D‐lactosamin mit Galactose‐Oxidase und β‐Galactosidase

Cited by 4 publications

References 38 publications

Synthesis of Novel Di‐ and Trisaccharide Mimetics with Non‐Glycosidic Amino Bridges

Synthesis of Novel Di‐ and Trisaccharide Mimetics with Non‐Glycosidic Amino Bridges

Die Heyns-Umlagerung in neuem Licht: außergewöhnlich einfache Synthese vonD-Lactosamin aus Lactulose

ChemInform Abstract: A Practical Method for the Synthesis of N‐Acetyl‐D‐lactosamine Derivatives by the Tandem Use of Galactose Oxidase and β‐ Galactosidase.

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