Enzymatic synthesis and NMR studies

Zoete, Marian C. Steverink-de; Kneepkens, Marcel F. M.; Waard, Pieter de; Oosterom, Marjolein Woudenberg-van; Slaghek, Ted M.; Gotlieb, Kees F.

doi:10.1039/a901381d

Cited by 10 publications

(4 citation statements)

References 15 publications

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“…Carbon atoms of the sucrose moiety were found in the range of 61.32 ~ 103.88 ppm. Data obtained on the NMR spectra of the sucrose octaacetate were in accordance with the previous report on the chemically enzymatic and naturally isolated, chemically and enzymatically modified sucrose octaacetates 11,12,15 . Therefore, the esters synthesized by conventional and ultrasound-assisted methods corresponded to the octa-O-acetylsucrose.…”

Section: F I G 2 -Ft-ir Spectra Of Sucrose (-) and Octa-o-acetylsucsupporting

confidence: 68%

“…This wide application of sucrose acetates requires effective and environmentally friendly methods for their production. The novel approach to the acetylation of sucrose includes lipase-catalyzed esterification of partially acetylated sucrose for the production of biodegradable and biocompatible emulsifiers 12 . Some reports have demonstrated the acetylation of various mono-and disaccharides with Ac 2 O-NaOAc under microwave and conventional conditions [13][14][15] .…”

Section: Introductionmentioning

confidence: 99%

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“Green” Synthesis of Sucrose Octaacetate and Characterization of Its Physicochemical Properties and Antimicrobial Activity

Petkova¹

2018

Chem.Biochem.Eng.Q.

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Sucrose octaacetate (octa-O-acetylsucrose) has been synthesized by esterification of sucrose with acetic anhydride using ultrasound-assisted irradiation. This sucrose ester is a white, water-insoluble substance with a bitter taste. The FT-IR and NMR spectra confirmed acetylation and revealed the hydrophobic incorporation in sucrose molecule. Furthermore, the foamability, foam stability, emulsification and antimicrobial properties of octa-O-acetylsucrose were evaluated. Foams and 50 % (oil/water) model emulsions were prepared with 2 % (w/w) octa-O-acetylsucrose. The obtained results demonstrate the formation of emulsions and foams with high stability (50-70 %). The antimicrobial activity of octa-O-acetylsucrose was evaluated against seventeen microorganisms (Gram-positive and Gram-negative bacteria, yeasts, and fungi). Octa-O-acetylsucrose inhibited the growth of fungi Penicillium sp., Rhizopus sp. and Fusarium moniliforme at 5 mg cm -3 , and yeasts Candida albicans at 1 mg cm -3. Inhibition against Gram-positive and Gram-negative bacteria was not observed. The obtained results demonstrate the potential applications of octa-O-acetylsucrose as a foaming agent, oil-in-water emulsion stabilizer, and antifungal substance in pharmaceutical and cosmetic preparations.

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Section: F I G 2 -Ft-ir Spectra Of Sucrose (-) and Octa-o-acetylsucsupporting

confidence: 68%

Section: Introductionmentioning

confidence: 99%

“Green” Synthesis of Sucrose Octaacetate and Characterization of Its Physicochemical Properties and Antimicrobial Activity

Petkova¹

2018

Chem.Biochem.Eng.Q.

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“…However, the degree of substitution (DS) is still low and the catalyst is expensive too. Very recently, two reports appeared in the literatures that use a base catalyzing acetylation of starch [13] and sucrose [14] with vinyl acetate in water. Because vinyl acetate is not sensible and miscible with water, the reaction mixture forms two layers reducing loss of acylating agent due to reaction with water, which is a major problem encountered for acetylation with acetic anhydride.…”

Section: Introductionmentioning

confidence: 99%

Convenient Per-O-Acetylation of Monosaccharides with Vinyl Acetate/ Na3PO4-H2O

Shi¹,

Zhang²,

Fu³

et al. 2006

LOC

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“…The first is based on the use of organic solvents suitable for the solubilization of both the saccharide and the acylating agent (Plou et al, 1995;Rich et al, 1995;Riva et al, 1988;Soedjak and Spradlin, 1994). The second is based on the hydrophobization of the sugar moiety by different methods: complexation with phenylboronic acids (Ikeda and Klibanov, 1993), formation of acetals (Sarney et al, 1994) or chemical acetylation (Steverink-de-Zoete et al, 1999). The derivatization is followed by solvent-free esterification with fatty acids.…”

Section: Influence Of the Reaction Mediummentioning

confidence: 99%

Enzymatic acylation of di- and trisaccharides with fatty acids: choosing the appropriate enzyme, support and solvent

Plou

Cruces

Ferrer

et al. 2002

Journal of Biotechnology

183

101

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Enzymatic synthesis of fatty acid esters of di-and trisaccharides is limited by the fact that most biological catalysts are inactivated by the polar solvents (e.g. dimethylsulfoxide, dimethylformamide) where these carbohydrates are soluble. This article reviews the methodologies developed to overcome this limitation, namely those involving control over the reaction medium, the enzyme and the support. We have proposed the use of mixtures of miscible solvents (e.g. dimethylsulfoxide and 2-methyl-2-butanol) as a general strategy to acylate enzymatically hydrophilic substrates.We observed that decreasing the hydrophobicity of the medium (i.e. lowering the percentage of DMSO) the molar ratio sucrose diesters vs. sucrose monoesters can be substantially enhanced. The different regioselectivity exhibited by several lipases and proteases makes feasible to synthesize different positional isomers, whose properties may vary considerably. In particular, the lipase from Thermomyces lanuginosus displays a notable selectivity for only one hydroxyl group in the acylation of sucrose, maltose, leucrose and maltotriose, compared with lipase from Candida antarctica. We have examined three immobilisation methods (adsorption on polypropylene, covalent coupling to Eupergit C, and silica-granulation) for sucrose acylation catalyzed by T. lanuginosus lipase. The morphology of the support affected significantly the reaction rate and/or the selectivity of the process.

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Enzymatic synthesis and NMR studies

Cited by 10 publications

References 15 publications

“Green” Synthesis of Sucrose Octaacetate and Characterization of Its Physicochemical Properties and Antimicrobial Activity

“Green” Synthesis of Sucrose Octaacetate and Characterization of Its Physicochemical Properties and Antimicrobial Activity

Convenient Per-O-Acetylation of Monosaccharides with Vinyl Acetate/ Na3PO4-H2O

Enzymatic acylation of di- and trisaccharides with fatty acids: choosing the appropriate enzyme, support and solvent

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