13C-nuclear magnetic resonance (NMR) spectra of O-acylglucoses. Additivity of shift parameters and its application to structure elucidations.

Yoshimoto, Kimihiro; Itatani, Yoshitaka; Tsuda, Yoshisuke

doi:10.1248/cpb.28.2065

Cited by 183 publications

(75 citation statements)

References 1 publication

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“…All the signals from the acrylate group are doublets (C a : 169.7 and 168.8 ppm, C c : 135.3 and 134.6 ppm, C b : 130.0 and 128.7 ppm), which indicate the presence of two different positional isomers in dexT70-VA. The ester positions on the glucopyranosyl residues were determined [29] based on the additional signals presented in the 13 C NMR spectrum (Fig. 3B) The two positional isomers in the main dextran backbone are at positions 2 and 3 in the glucopyranosyl residues, and the respective 13 C-NMR assignments are presented in Table 2.…”

Section: Characterization Of Dext70-va Obtained Enzymatically By Nmr mentioning

confidence: 99%

Enzymatic synthesis of dextran-containing hydrogels

2002

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Dextran, a natural glucose-containing polysaccharide, has been acylated by Proleather FG-F and lipase AY, a protease and lipase from Bacillus sp. and Candida rugosa, respectively, in anhydrous dimethylsulfoxide in the presence of vinyl acrylate (VA). The efficiency of the reaction in the presence of Proleather FG-F and the isolated yields were ca. 71% and 45%, respectively. Dextran derivatized with VA (dexT70-VA) was characterized by gel permeation chromatography and its structure was established by NMR indicating two positional isomers at the 2 and 3 positions on the glucose moieties in equal amounts. Furthermore, the dextran glucopyranose residues were mono-substituted. The benefits of the biocatalytic synthesis of dextran acrylates was demonstrated using 4-dimethylaminopyridine as a chemical catalyst. Gels were prepared by free radical polymerization of aqueous solutions of dexT70-VA with different degrees of substitution and monomer concentrations. Intermolecular linkages and physical entanglements are predominantly formed by concentrated solutions, however, a part of the acrylate groups did not react. Gel pore sizes were calculated from swelling experiments and ranged from ca. 18 to 182 ( A. r

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Section: Characterization Of Dext70-va Obtained Enzymatically By Nmr mentioning

confidence: 99%

Enzymatic synthesis of dextran-containing hydrogels

2002

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“…It was expected that, analogous to most chemical reactions (Clode et al, 1985;Ogawa and Matsui, 1977), sucrose would be acylated at one of the three primary hydroxyl positions (6OH, 1OH, and 6ЈOH) and acylation at position 6 of the sucrose should result in a downfield shift of the peak at C6 and an upfield shift in the peak at C5 (Patil et al, 1991;Rich et al, 1995;Yoshimoto et al, 1980). The 13 C DEPT shows conclusively that the CH 2 signal from 6OH is shifted to 63.6 ppm from its unsubstituted position of ca.…”

Section: Determination Of Regioselectivity On Sucrosementioning

confidence: 99%

Effect of salt hydrate pair on lipase-catalyzed regioselective monoacylation of sucrose

Kim

Han

Yoon

et al. 1998

Biotechnol. Bioeng.

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“…Because hepatic ASGPR had a greater affinity for GalNAc than for ␤-galactoside, this result demonstrates that the precipitated ASGPRs are hepatic ASGPRs. Using the technique of 13 C NMR analysis of carbohydrates (43), PMglc showed a downfield shift of the peak at C-6 from the results of NMR analysis (data not shown). These shifts resulted from the transesterification of glucose with vinyl methacrylate at the C-6 position of glucose.…”

Section: Detection Of Asgpr With Gel Particles Containing 6-omethacrymentioning

confidence: 95%

Specific Binding of Glucose-derivatized Polymers to the Asialoglycoprotein Receptor of Mouse Primary Hepatocytes

Kim¹,

Goto²,

Akaike³

2001

Journal of Biological Chemistry

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In this study, we designed a novel amphiphilic poly-(p-Nvinylbenzyl-D-glucuronamide) (PV6Gna) modified at the 6-OH position of glucose for hepatocyte recognition to address the mechanism of the interaction between mouse primary hepatocytes and the PV6Gna. PV6Gna bound to lectins specific for glucose but not galactose as did other glucose-derivatized polymers. However, hepatocyte adhesion onto the PV6Gna surface was inhibited in the presence of galactose and its analogues but not in the presence of glucose and its analogues. We also showed that hepatocyte adhesion to the PV6Gna surface was inhibited dose dependently by asialofetuin (ASF). Interactions between soluble PV6Gna and hepatocytes were inhibited by GalNAc, ASF, and EGTA in flow cytometry analysis using fluorescein isothiocyanate-conjugated PV6Gna. Hepatocyte adhesion to the PV6Gna surface was inhibited more effectively by GalNAc than by methyl ␤-D-galactose. In flow cytometry analysis and cell adhesion assay, ASF competed for the inhibition of interaction between PV6Gna and hepatocytes 0.5-4 ؋ 10 5

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13C-nuclear magnetic resonance (NMR) spectra of O-acylglucoses. Additivity of shift parameters and its application to structure elucidations.

Cited by 183 publications

References 1 publication

Enzymatic synthesis of dextran-containing hydrogels

Enzymatic synthesis of dextran-containing hydrogels

Effect of salt hydrate pair on lipase-catalyzed regioselective monoacylation of sucrose

Specific Binding of Glucose-derivatized Polymers to the Asialoglycoprotein Receptor of Mouse Primary Hepatocytes

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