Molecular sieves provoke multiple substitutions in the enzymatic synthesis of fructose oligosaccharide–lauryl esters

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Abstract

The cause of discrepancies in the literature regarding the specificity of immobilized Candida antarctica lipase B in the acylation of oligosaccharides was examined. Molecular sieves, generally used to control the water content during acylation reactions, turned out to have an important role in this. It was proven that molecular sieves alone can catalyze the acylation of fructose oligomers using vinyl laurate, leading to multiple substitution of the oligomers. This effect was the most profound at conditions unfavorable for the enzyme, because this resulted in a relatively high concentration of the chemically produced adducts. The enzyme alone catalyzed the formation of monosubstituted oligomers. It was proven that even solvent pre-drying by molecular sieves already causes the release of catalyzing compounds to the liquid, leading to subsequent catalysis. These findings should be taken into account when applying molecular sieves in this type of reactions in the future. Molecular sieves could, moreover, be used as a catalyst when multiple substitution is desired.
Original languageEnglish
Pages (from-to)183-189
JournalJournal of Molecular Catalysis. B, Enzymatic
Volume62
Issue number2
DOIs
Publication statusPublished - 2010

Fingerprint

Fructose
Acylation
Molecular sieves
Esters
Substitution reactions
Oligomers
Laurates
Enzymes
Catalysis
Oligosaccharides
Candida
Lipases
Water
Water content
Drying
Catalysts
Liquids

Keywords

  • regioselective acylation
  • organic media
  • esterification
  • lipase
  • sucrose
  • acid
  • hydrolases
  • cellulose
  • al-mcm-41
  • zeolites

Cite this

@article{b8f17bf9ca9243f0a35344e74ad3618f,
title = "Molecular sieves provoke multiple substitutions in the enzymatic synthesis of fructose oligosaccharide–lauryl esters",
abstract = "The cause of discrepancies in the literature regarding the specificity of immobilized Candida antarctica lipase B in the acylation of oligosaccharides was examined. Molecular sieves, generally used to control the water content during acylation reactions, turned out to have an important role in this. It was proven that molecular sieves alone can catalyze the acylation of fructose oligomers using vinyl laurate, leading to multiple substitution of the oligomers. This effect was the most profound at conditions unfavorable for the enzyme, because this resulted in a relatively high concentration of the chemically produced adducts. The enzyme alone catalyzed the formation of monosubstituted oligomers. It was proven that even solvent pre-drying by molecular sieves already causes the release of catalyzing compounds to the liquid, leading to subsequent catalysis. These findings should be taken into account when applying molecular sieves in this type of reactions in the future. Molecular sieves could, moreover, be used as a catalyst when multiple substitution is desired.",
keywords = "regioselective acylation, organic media, esterification, lipase, sucrose, acid, hydrolases, cellulose, al-mcm-41, zeolites",
author = "{ter Haar}, R. and H.A. Schols and {van den Broek}, L.A.M. and D. Saglam and A.E. Frissen and C.G. Boeriu and H. Gruppen",
year = "2010",
doi = "10.1016/j.molcatb.2009.10.008",
language = "English",
volume = "62",
pages = "183--189",
journal = "Journal of Molecular Catalysis. B, Enzymatic",
issn = "1381-1177",
publisher = "Elsevier",
number = "2",

}

TY - JOUR

T1 - Molecular sieves provoke multiple substitutions in the enzymatic synthesis of fructose oligosaccharide–lauryl esters

AU - ter Haar, R.

AU - Schols, H.A.

AU - van den Broek, L.A.M.

AU - Saglam, D.

AU - Frissen, A.E.

AU - Boeriu, C.G.

AU - Gruppen, H.

PY - 2010

Y1 - 2010

N2 - The cause of discrepancies in the literature regarding the specificity of immobilized Candida antarctica lipase B in the acylation of oligosaccharides was examined. Molecular sieves, generally used to control the water content during acylation reactions, turned out to have an important role in this. It was proven that molecular sieves alone can catalyze the acylation of fructose oligomers using vinyl laurate, leading to multiple substitution of the oligomers. This effect was the most profound at conditions unfavorable for the enzyme, because this resulted in a relatively high concentration of the chemically produced adducts. The enzyme alone catalyzed the formation of monosubstituted oligomers. It was proven that even solvent pre-drying by molecular sieves already causes the release of catalyzing compounds to the liquid, leading to subsequent catalysis. These findings should be taken into account when applying molecular sieves in this type of reactions in the future. Molecular sieves could, moreover, be used as a catalyst when multiple substitution is desired.

AB - The cause of discrepancies in the literature regarding the specificity of immobilized Candida antarctica lipase B in the acylation of oligosaccharides was examined. Molecular sieves, generally used to control the water content during acylation reactions, turned out to have an important role in this. It was proven that molecular sieves alone can catalyze the acylation of fructose oligomers using vinyl laurate, leading to multiple substitution of the oligomers. This effect was the most profound at conditions unfavorable for the enzyme, because this resulted in a relatively high concentration of the chemically produced adducts. The enzyme alone catalyzed the formation of monosubstituted oligomers. It was proven that even solvent pre-drying by molecular sieves already causes the release of catalyzing compounds to the liquid, leading to subsequent catalysis. These findings should be taken into account when applying molecular sieves in this type of reactions in the future. Molecular sieves could, moreover, be used as a catalyst when multiple substitution is desired.

KW - regioselective acylation

KW - organic media

KW - esterification

KW - lipase

KW - sucrose

KW - acid

KW - hydrolases

KW - cellulose

KW - al-mcm-41

KW - zeolites

U2 - 10.1016/j.molcatb.2009.10.008

DO - 10.1016/j.molcatb.2009.10.008

M3 - Article

VL - 62

SP - 183

EP - 189

JO - Journal of Molecular Catalysis. B, Enzymatic

JF - Journal of Molecular Catalysis. B, Enzymatic

SN - 1381-1177

IS - 2

ER -