Stereoselective Access to the β‐<scp>D</scp>‐<i>N</i>‐Acetylhexosaminyl‐(1→4)‐1‐deoxy‐<scp>D</scp>‐nojirimycin Disaccharide Series Avoiding the Glycosylation Reaction

Guazzelli, Lorenzo; Catelani, Giorgio; D’Andrea, Felicia; Gragnani, Tiziana; Griselli, A

doi:10.1002/ejoc.201402555

Cited by 8 publications

(7 citation statements)

References 44 publications

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“…Keto-disaccharides such as maltulose, palatinose, lactulose, cellobiulose, and melibiulose are of great interest in studies of food nutrition 1) and biomass transformation, 2,3) as well as in organic synthesis, because they are natural chiral molecules. 4) As a food additive, for example, lactulose promotes the growth of Bifidobacterium 5) and decreases the formation of putrefactive products, 6) increasing health benefits for human beings.…”

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confidence: 99%

Production of keto-disaccharides from aldo-disaccharides in subcritical aqueous ethanol

Gao

Kobayashi

Adachi

2016

Bioscience, Biotechnology, and Biochemistry

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Isomerization of disaccharides (maltose, isomaltose, cellobiose, lactose, melibiose, palatinose, sucrose, and trehalose) was investigated in subcritical aqueous ethanol. A marked increase in the isomerization of aldo-disaccharides to keto-disaccharides was noted and their hydrolytic reactions were suppressed with increasing ethanol concentration. Under any study condition, the maximum yield of keto-disaccharides produced from aldo-disaccharides linked by β-glycosidic bond was higher than that produced from aldo-disaccharides linked by α-glycosidic bond. Palatinose, a keto-disaccharide, mainly underwent decomposition rather than isomerization in subcritical water and subcritical aqueous ethanol. No isomerization was noted for the non-reducing disaccharides trehalose and sucrose. The rate constant of maltose to maltulose isomerization almost doubled by changing solvent from subcritical water to 80 wt% aqueous ethanol at 220 °C. Increased maltose monohydrate concentration in feed decreased the conversion of maltose and the maximum yield of maltulose, but increased the productivity of maltulose. The maximum productivity of maltulose was ca. 41 g/(h kg-solution).

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confidence: 99%

Production of keto-disaccharides from aldo-disaccharides in subcritical aqueous ethanol

Gao

Kobayashi

Adachi

2016

Bioscience, Biotechnology, and Biochemistry

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“…Several different synthetic approaches have been explored thus far for preparing tetrasaccharide 1 , which is formally constituted by a lactose unit linked to an N -acetyl-lactosamine unit through a beta 1→6 glycosidic linkage. Thanks to a long-lasting experience in modifying the structure of lactose [31,32,33,34], we decided to use this natural disaccharide as the starting material for the preparation of lactose/lacturonic building block donors, while we built up lactosamine acceptors from suitably protected monosaccharide derivatives. The general design of the planned synthetic strategy is reported in Scheme 1, with the negative charge located on the galactose frame of the lactose unit (X) and the positive charge inserted either on the galactose part of the lactosamine unit (Y) or on the external linker (R).…”

Section: Resultsmentioning

confidence: 99%

Selectively Charged and Zwitterionic Analogues of the Smallest Immunogenic Structure of Streptococcus Pneumoniae Type 14

et al. 2019

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Zwitterionic polysaccharides (ZPs) have been shown in recent years to display peculiar immunological properties, thus attracting the interest of the carbohydrate research community. To fully elucidate the mechanisms underlying these properties and exploit the potential of this kind of structures, in depth studies are still required. In this context, the preparation of two cationic, an anionic, as well as two zwitterionic tetrasaccharide analogues of the smallest immunogenic structure of Streptococcus pneumoniae type 14 (SP14) capsular polysaccharide are presented. By exploiting a block strategy, the negative charge has been installed on the non-reducing end of the lactose unit of the tetrasaccharide and the positive charge either on the non-reducing end of the lactosamine moiety or on an external linker. These structures have then been tested by competitive ELISA, showing that the structural variations we made do not modify the affinity of the neutral compound to binding to a specific antibody. However, lower efficacies than the natural SP14 compound were observed. The results obtained, although promising, point to the need to further elongate the polysaccharide structure, which is likely too short to cover the entire epitopes.

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“…Derivative 6a was also reacted with O-(arylmethyl)hydroxylamine hydrochloride 7a bearing an electron-donor group (methoxy group) (Scheme 3), in the condition of the intramolecular double reductive amination (aminocyclisation) following a protocol previously reported by us (NaBH 3 CN, MeOH, 60 C, 96 h) 15,19,26 or performed in presence of AcOH (pH 5-6) 27 .In both cases the purification of the crude products by flash chromatography on silica gel afforded the pure azasugar 12 (D-galacto) in a rather low yield (15-20%), together with the mixture of E/Z-8 oxime (10-12%) and the corresponding 6-O-deprotected E/Z-10 isomers (40-43%).…”

Section: Chemistrymentioning

confidence: 99%

Oxy-imino saccharidic derivatives as a new structural class of aldose reductase inhibitors endowed with anti-oxidant activity

D’Andrea

Sartini

Piano

et al. 2020

Journal of Enzyme Inhibition and Medicinal Chemistry

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Aldose reductase is a key enzyme in the development of long term diabetic complications and its inhibition represents a viable therapeutic solution for people affected by these pathologies. Therefore, the search for effective aldose reductase inhibitors is a timely and pressing challenge. Herein we describe the access to a novel class of oxyimino derivatives, obtained by reaction of a 1,5-dicarbonyl substrate with O-(arylmethyl)hydroxylamines. The synthesised compounds proved to be active against the target enzyme. The best performing inhibitor, compound (Z)-8, proved also to reduce both cell death and the apoptotic process when tested in an in vitro model of diabetic retinopathy made of photoreceptor-like 661w cell line exposed to high-glucose medium, counteracting oxidative stress triggered by hyperglycaemic conditions.

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Stereoselective Access to the β‐D‐N‐Acetylhexosaminyl‐(1→4)‐1‐deoxy‐D‐nojirimycin Disaccharide Series Avoiding the Glycosylation Reaction

Cited by 8 publications

References 44 publications

Production of keto-disaccharides from aldo-disaccharides in subcritical aqueous ethanol

Production of keto-disaccharides from aldo-disaccharides in subcritical aqueous ethanol

Selectively Charged and Zwitterionic Analogues of the Smallest Immunogenic Structure of Streptococcus Pneumoniae Type 14

Oxy-imino saccharidic derivatives as a new structural class of aldose reductase inhibitors endowed with anti-oxidant activity

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