Equilibrium yield of n-alkyl-β-d-glucoside through condensation of glucose and n-alcohol by β-glucosidase in a biphasic system

Chaiya Panintrarux, Shuji Adachi, Yoichi Araki, Yukitaka Kimura, Ryuichi Matsuno

Research output: Contribution to journalArticle

77 Citations (Scopus)

Abstract

The β-glucosidase-catalyzed synthesis of n-alkyl-β-d-glucosides through the condensation of glucose and n-alcohols with alkyl chain lengths of 6 to 12 was carried out in a biphasic system, where the organic phase consisted only of an alcohol substrate. All the alcohols tested were condensed with glucose to give the corresponding n-alkyl-β-d-glucosides. An equation was formulated to predict the equilibrium yields of n-alkyl-β-d-glucosides under various conditions, and its validity was experimentally verified. The equilibrium constant for the formation of n-alkyl-β-d-glucosides was independent of the alkyl chain length and was 1.90 at 60°C. The volume ratio of the organic to the aqueous phase was a factor significantly affecting the equilibrium yield. It was also shown that the synthesis at lower initial glucose concentrations effectively yielded alkylglucosides with less β-glucobiose formation.

Original languageEnglish
Pages (from-to)32-40
Number of pages9
JournalEnzyme and Microbial Technology
Volume17
Issue number1
DOIs
Publication statusPublished - 1995
Externally publishedYes

Fingerprint

Glucosidases
Glucosides
Glucose
Condensation
Alcohols
Chain length
Equilibrium constants
Substrates

Keywords

  • Alkylglucosides
  • biphasic system
  • surfactant
  • β-glucosidase

ASJC Scopus subject areas

  • Biochemistry
  • Biotechnology
  • Applied Microbiology and Biotechnology

Cite this

Equilibrium yield of n-alkyl-β-d-glucoside through condensation of glucose and n-alcohol by β-glucosidase in a biphasic system. / Panintrarux, Chaiya; Adachi, Shuji; Araki, Yoichi; Kimura, Yukitaka; Matsuno, Ryuichi.

In: Enzyme and Microbial Technology, Vol. 17, No. 1, 1995, p. 32-40.

Research output: Contribution to journalArticle

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AU - Araki, Yoichi

AU - Kimura, Yukitaka

AU - Matsuno, Ryuichi

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N2 - The β-glucosidase-catalyzed synthesis of n-alkyl-β-d-glucosides through the condensation of glucose and n-alcohols with alkyl chain lengths of 6 to 12 was carried out in a biphasic system, where the organic phase consisted only of an alcohol substrate. All the alcohols tested were condensed with glucose to give the corresponding n-alkyl-β-d-glucosides. An equation was formulated to predict the equilibrium yields of n-alkyl-β-d-glucosides under various conditions, and its validity was experimentally verified. The equilibrium constant for the formation of n-alkyl-β-d-glucosides was independent of the alkyl chain length and was 1.90 at 60°C. The volume ratio of the organic to the aqueous phase was a factor significantly affecting the equilibrium yield. It was also shown that the synthesis at lower initial glucose concentrations effectively yielded alkylglucosides with less β-glucobiose formation.

AB - The β-glucosidase-catalyzed synthesis of n-alkyl-β-d-glucosides through the condensation of glucose and n-alcohols with alkyl chain lengths of 6 to 12 was carried out in a biphasic system, where the organic phase consisted only of an alcohol substrate. All the alcohols tested were condensed with glucose to give the corresponding n-alkyl-β-d-glucosides. An equation was formulated to predict the equilibrium yields of n-alkyl-β-d-glucosides under various conditions, and its validity was experimentally verified. The equilibrium constant for the formation of n-alkyl-β-d-glucosides was independent of the alkyl chain length and was 1.90 at 60°C. The volume ratio of the organic to the aqueous phase was a factor significantly affecting the equilibrium yield. It was also shown that the synthesis at lower initial glucose concentrations effectively yielded alkylglucosides with less β-glucobiose formation.

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