Influence of glucose solubility and dissolution rate on the kinetics of lipase catalyzed synthesis of glucose laurate in 2- methyl 2-butanol

M.V. Flores, K. Naraghi, J.M. Engasser, P.J. Halling

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

The lipase catalyzed acylation of glucose by dodecanoic acid in 2-methyl 2-butanol was studied. The initial reaction rate was strongly dependent on the dissolved glucose concentration in the medium. Several methods were shown to increase dissolved glucose concentrations and initial reaction rates, namely, the use of solid beta-glucose, amorphous solid glucose, and supersaturated glucose solution. Supersaturated glucose solutions in 2-methyl 2-butanol showed a high stability even in the presence of solid crystalline glucose. During the reaction, the dissolved glucose concentration falls as the reaction proceeds, before recovering later as more of the excess solid dissolves. However, the ester synthesis rate continues to fall even after glucose concentration reaches its minimum, so glucose dissolution rate limitation is not responsible for the synthesis rate decline. Experiments with added molecular sieves show that the main reason is the accumulation of product water. In the presence of molecular sieves, 70% of glucose was converted to ester, independent of the initial soluble glucose in the medium.
Original languageEnglish
Pages (from-to)814-820
Number of pages6
JournalBiotechnology and Bioengineering
Volume78
Issue number7
DOIs
Publication statusPublished - 30 Jun 2002

Fingerprint

Laurates
Enzyme kinetics
Lipases
Lipase
Butenes
Solubility
Glucose
Dissolution
Kinetics
lauric acid
Molecular sieves
tert-amyl alcohol
Reaction rates
Esters
Acylation

Keywords

  • sugar esters
  • nonaqueous media
  • lipase
  • glucose Fatty-acid esters
  • supersaturated substrate solutions
  • enzymatic-synthesis
  • organic-solvents
  • sugars
  • acylation
  • fructose
  • media
  • transformations
  • esterification

Cite this

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title = "Influence of glucose solubility and dissolution rate on the kinetics of lipase catalyzed synthesis of glucose laurate in 2- methyl 2-butanol",
abstract = "The lipase catalyzed acylation of glucose by dodecanoic acid in 2-methyl 2-butanol was studied. The initial reaction rate was strongly dependent on the dissolved glucose concentration in the medium. Several methods were shown to increase dissolved glucose concentrations and initial reaction rates, namely, the use of solid beta-glucose, amorphous solid glucose, and supersaturated glucose solution. Supersaturated glucose solutions in 2-methyl 2-butanol showed a high stability even in the presence of solid crystalline glucose. During the reaction, the dissolved glucose concentration falls as the reaction proceeds, before recovering later as more of the excess solid dissolves. However, the ester synthesis rate continues to fall even after glucose concentration reaches its minimum, so glucose dissolution rate limitation is not responsible for the synthesis rate decline. Experiments with added molecular sieves show that the main reason is the accumulation of product water. In the presence of molecular sieves, 70{\%} of glucose was converted to ester, independent of the initial soluble glucose in the medium.",
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Influence of glucose solubility and dissolution rate on the kinetics of lipase catalyzed synthesis of glucose laurate in 2- methyl 2-butanol. / Flores, M.V.; Naraghi, K.; Engasser, J.M.; Halling, P.J.

In: Biotechnology and Bioengineering, Vol. 78, No. 7, 30.06.2002, p. 814-820.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Influence of glucose solubility and dissolution rate on the kinetics of lipase catalyzed synthesis of glucose laurate in 2- methyl 2-butanol

AU - Flores, M.V.

AU - Naraghi, K.

AU - Engasser, J.M.

AU - Halling, P.J.

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Y1 - 2002/6/30

N2 - The lipase catalyzed acylation of glucose by dodecanoic acid in 2-methyl 2-butanol was studied. The initial reaction rate was strongly dependent on the dissolved glucose concentration in the medium. Several methods were shown to increase dissolved glucose concentrations and initial reaction rates, namely, the use of solid beta-glucose, amorphous solid glucose, and supersaturated glucose solution. Supersaturated glucose solutions in 2-methyl 2-butanol showed a high stability even in the presence of solid crystalline glucose. During the reaction, the dissolved glucose concentration falls as the reaction proceeds, before recovering later as more of the excess solid dissolves. However, the ester synthesis rate continues to fall even after glucose concentration reaches its minimum, so glucose dissolution rate limitation is not responsible for the synthesis rate decline. Experiments with added molecular sieves show that the main reason is the accumulation of product water. In the presence of molecular sieves, 70% of glucose was converted to ester, independent of the initial soluble glucose in the medium.

AB - The lipase catalyzed acylation of glucose by dodecanoic acid in 2-methyl 2-butanol was studied. The initial reaction rate was strongly dependent on the dissolved glucose concentration in the medium. Several methods were shown to increase dissolved glucose concentrations and initial reaction rates, namely, the use of solid beta-glucose, amorphous solid glucose, and supersaturated glucose solution. Supersaturated glucose solutions in 2-methyl 2-butanol showed a high stability even in the presence of solid crystalline glucose. During the reaction, the dissolved glucose concentration falls as the reaction proceeds, before recovering later as more of the excess solid dissolves. However, the ester synthesis rate continues to fall even after glucose concentration reaches its minimum, so glucose dissolution rate limitation is not responsible for the synthesis rate decline. Experiments with added molecular sieves show that the main reason is the accumulation of product water. In the presence of molecular sieves, 70% of glucose was converted to ester, independent of the initial soluble glucose in the medium.

KW - sugar esters

KW - nonaqueous media

KW - lipase

KW - glucose Fatty-acid esters

KW - supersaturated substrate solutions

KW - enzymatic-synthesis

KW - organic-solvents

KW - sugars

KW - acylation

KW - fructose

KW - media

KW - transformations

KW - esterification

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