Lipase-catalyzed synthesis of fatty acid esters of trisaccharides

Jose L. Gonzalez-Alfonso; Leticia Casas-Godoy; Javier Arrizon; Daniel Arrieta-Baez; Antonio O. Ballesteros; Georgina Sandoval; Francisco J. Plou

doi:10.1007/978-1-4939-8672-9_15

Lipase-catalyzed synthesis of fatty acid esters of trisaccharides

Jose L. Gonzalez-Alfonso, Leticia Casas-Godoy, Javier Arrizon, Daniel Arrieta-Baez, Antonio O. Ballesteros, Georgina Sandoval, Francisco J. Plou

Centro de Nanociencias y Micro y Nanotecnologías (CNMN)

Research output: Chapter in Book/Report/Conference proceeding › Chapter › peer-review

2 Scopus citations

Abstract

Carbohydrate fatty acid esters have a broad spectrum of applications in the food, cosmetic, and pharmaceutical industries. The enzyme-catalyzed acylation is significantly more selective than the chemical process and is carried out at milder conditions. Compared with mono- and disaccharides, the acylation of trisaccharides has been less studied. However, trisaccharide esters display notable bioactive properties, probably due to the higher hydrophilicity of the sugar head group. In this chapter, we describe the acylation of two trisaccharides, maltotriose and 1-kestose, catalyzed by different immobilized lipases, using vinyl esters as acyl donors. To illustrate the potential of such compounds, the antitumor activity of 6″-O-palmitoyl-maltotriose is shown.

Original language	English
Title of host publication	Methods in Molecular Biology
Publisher	Humana Press Inc.
Pages	287-296
Number of pages	10
DOIs	https://doi.org/10.1007/978-1-4939-8672-9_15
State	Published - 2018

Publication series

Name	Methods in Molecular Biology
Volume	1835
ISSN (Print)	1064-3745

Keywords

1-Kestose
Acylation
Lipases
Maltotriose
Regioselectivity
Sugar esters
Surfactants
Transesterification

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10.1007/978-1-4939-8672-9_15

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abstract = "Carbohydrate fatty acid esters have a broad spectrum of applications in the food, cosmetic, and pharmaceutical industries. The enzyme-catalyzed acylation is significantly more selective than the chemical process and is carried out at milder conditions. Compared with mono- and disaccharides, the acylation of trisaccharides has been less studied. However, trisaccharide esters display notable bioactive properties, probably due to the higher hydrophilicity of the sugar head group. In this chapter, we describe the acylation of two trisaccharides, maltotriose and 1-kestose, catalyzed by different immobilized lipases, using vinyl esters as acyl donors. To illustrate the potential of such compounds, the antitumor activity of 6″-O-palmitoyl-maltotriose is shown.",

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AU - Gonzalez-Alfonso, Jose L.

AU - Casas-Godoy, Leticia

AU - Arrizon, Javier

AU - Arrieta-Baez, Daniel

AU - Ballesteros, Antonio O.

AU - Sandoval, Georgina

AU - Plou, Francisco J.

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N2 - Carbohydrate fatty acid esters have a broad spectrum of applications in the food, cosmetic, and pharmaceutical industries. The enzyme-catalyzed acylation is significantly more selective than the chemical process and is carried out at milder conditions. Compared with mono- and disaccharides, the acylation of trisaccharides has been less studied. However, trisaccharide esters display notable bioactive properties, probably due to the higher hydrophilicity of the sugar head group. In this chapter, we describe the acylation of two trisaccharides, maltotriose and 1-kestose, catalyzed by different immobilized lipases, using vinyl esters as acyl donors. To illustrate the potential of such compounds, the antitumor activity of 6″-O-palmitoyl-maltotriose is shown.

AB - Carbohydrate fatty acid esters have a broad spectrum of applications in the food, cosmetic, and pharmaceutical industries. The enzyme-catalyzed acylation is significantly more selective than the chemical process and is carried out at milder conditions. Compared with mono- and disaccharides, the acylation of trisaccharides has been less studied. However, trisaccharide esters display notable bioactive properties, probably due to the higher hydrophilicity of the sugar head group. In this chapter, we describe the acylation of two trisaccharides, maltotriose and 1-kestose, catalyzed by different immobilized lipases, using vinyl esters as acyl donors. To illustrate the potential of such compounds, the antitumor activity of 6″-O-palmitoyl-maltotriose is shown.

KW - 1-Kestose

KW - Acylation

KW - Lipases

KW - Maltotriose

KW - Regioselectivity

KW - Sugar esters

KW - Surfactants

KW - Transesterification

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T3 - Methods in Molecular Biology

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BT - Methods in Molecular Biology

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ER -

Lipase-catalyzed synthesis of fatty acid esters of trisaccharides

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Keywords

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