Protease-catalyzed regioselective esterification of sugars and related compounds in anhydrous dimethylformamide

Riva, Sergio; Chopineau, Joël; Kieboom, A. P. G.; Klibanov, Alexander M.

doi:10.1021/ja00210a045

Cited by 463 publications

(150 citation statements)

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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).…”

Section: Influence Of the Reaction Mediummentioning

confidence: 99%

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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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Section: Influence Of the Reaction Mediummentioning

confidence: 99%

“…The temperature of the column was kept constant at 40°C. (Riva et al, 1988) B. fulva lipase (Ku et al, 1995) C. antarctica lipase (Woudenberg et al, 1996) T. lanuginosus lipase (Ferrer et al, 2000a) …”

Section: Effect Of Sugar Ester Structure On Functional Propertiesmentioning

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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show abstract

“…With increasing carbon number of a fatty acid or molecule size, the steric hindrance is involved resulting in low efficiency of the enzymatic reaction (Riva et al, 1988;Wang et al, 1988;Carrea et al, 1989). This fact was experimentally confirmed by Katsoura et al (2006) and by Viskupicova & Ondrejovic (2007) whose results showed higher performance of the naringin and rutin esterification when fatty acids up to C10 were introduced.…”

Section: Acyl Donormentioning

confidence: 77%

Enzyme-Mediated Preparation of Flavonoid Esters and Their Applications

Viskupičová¹,

Ondrejovič²,

Maliar³

2012

Biochemistry

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“…[10][11][12][13] It is not easy to mix carbohydrates, especially di-and oligosaccharides, and acyl donors in the reaction medium because of their differing solubility. The use of such hydrophilic organic solvents as pyridine and dimethylformamide (DMF) is one approach for rendering soluble the substrate in an enzyme reaction.…”

Section: -O--d-glucopyranosyl-l-ascorbic Acid (Aa-2gmentioning

confidence: 99%

Protease-Catalyzed Monoacylation of 2-O-α-D-Glucopyranosyl-L-ascorbic Acid in Three Solvent Systems

Tai

Iwaoka

Mori

et al. 2010

Bioscience, Biotechnology, and Biochemistry

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Protease-catalyzed regioselective esterification of sugars and related compounds in anhydrous dimethylformamide

Cited by 463 publications

References 1 publication

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

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

Enzyme-Mediated Preparation of Flavonoid Esters and Their Applications

Protease-Catalyzed Monoacylation of 2-O-α-D-Glucopyranosyl-L-ascorbic Acid in Three Solvent Systems

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