Biocatalytic acylation of sugar alcohols by 3-(4-hydroxyphenyl)propionic acid

R. Croitoru, F. Fitigau, L.A.M. van den Broek, A.E. Frissen, C.G. Boeriu

Research output: Contribution to journalArticleAcademicpeer-review

13 Citations (Scopus)

Abstract

Enzymatic synthesis of aromatic esters of four different sugar alcohols (xylitol, arabitol, mannitol, and sorbitol) with 3-(4-hydroxyphenyl)propionic acid was performed in organic solvent medium, using immobilized Candida antarctica lipase (Novozyme 435), and molecular sieves for control of the water content. The influence of reaction parameters on the conversion has been investigated, including reaction time, temperature, alcohol/acid molar ratio, and enzyme amount. The highest conversions (94% for xylitol, 98% for arabitol, 80% for mannitol, and 93% for sorbitol) were obtained in pure tert-butanol at 60 °C and 72 h reaction time, 0.3 alcohol/acid molar ratio, and 0.5 g/mol enzyme/substrate ratio. The isolated new sugar alcohols esters were identified by different spectral analyses. MALDI-TOF MS analysis showed the formation of monoesters, diesters, and small quantities of triesters for all investigated sugar alcohols. The catalytic efficiency of the enzyme was higher for the pentitol substrates, decreasing in the following order: arabitol > xylitol > sorbitol > mannitol. These new compounds could have interesting applications in food, pharmaceutical and cosmetic formulations
Original languageEnglish
Pages (from-to)1894-1902
JournalProcess Biochemistry
Volume47
Issue number12
DOIs
Publication statusPublished - 2012

Fingerprint

Sugar Alcohols
Xylitol
Acylation
Propionic acid
Sorbitol
Mannitol
Enzymes
Esters
Alcohols
tert-Butyl Alcohol
Drug Compounding
Acids
Candida
Matrix-Assisted Laser Desorption-Ionization Mass Spectrometry
Molecular sieves
Lipases
Substrates
Lipase
Butenes
Cosmetics

Keywords

  • lipase-catalyzed esterification
  • candida-antarctica lipase
  • phenolic-acids
  • enzymatic preparation
  • organic media
  • esters
  • glycosides
  • condensation
  • copolyesters
  • solvents

Cite this

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title = "Biocatalytic acylation of sugar alcohols by 3-(4-hydroxyphenyl)propionic acid",
abstract = "Enzymatic synthesis of aromatic esters of four different sugar alcohols (xylitol, arabitol, mannitol, and sorbitol) with 3-(4-hydroxyphenyl)propionic acid was performed in organic solvent medium, using immobilized Candida antarctica lipase (Novozyme 435), and molecular sieves for control of the water content. The influence of reaction parameters on the conversion has been investigated, including reaction time, temperature, alcohol/acid molar ratio, and enzyme amount. The highest conversions (94{\%} for xylitol, 98{\%} for arabitol, 80{\%} for mannitol, and 93{\%} for sorbitol) were obtained in pure tert-butanol at 60 °C and 72 h reaction time, 0.3 alcohol/acid molar ratio, and 0.5 g/mol enzyme/substrate ratio. The isolated new sugar alcohols esters were identified by different spectral analyses. MALDI-TOF MS analysis showed the formation of monoesters, diesters, and small quantities of triesters for all investigated sugar alcohols. The catalytic efficiency of the enzyme was higher for the pentitol substrates, decreasing in the following order: arabitol > xylitol > sorbitol > mannitol. These new compounds could have interesting applications in food, pharmaceutical and cosmetic formulations",
keywords = "lipase-catalyzed esterification, candida-antarctica lipase, phenolic-acids, enzymatic preparation, organic media, esters, glycosides, condensation, copolyesters, solvents",
author = "R. Croitoru and F. Fitigau and {van den Broek}, L.A.M. and A.E. Frissen and C.G. Boeriu",
year = "2012",
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pages = "1894--1902",
journal = "Process Biochemistry",
issn = "1359-5113",
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Biocatalytic acylation of sugar alcohols by 3-(4-hydroxyphenyl)propionic acid. / Croitoru, R.; Fitigau, F.; van den Broek, L.A.M.; Frissen, A.E.; Boeriu, C.G.

In: Process Biochemistry, Vol. 47, No. 12, 2012, p. 1894-1902.

Research output: Contribution to journalArticleAcademicpeer-review

TY - JOUR

T1 - Biocatalytic acylation of sugar alcohols by 3-(4-hydroxyphenyl)propionic acid

AU - Croitoru, R.

AU - Fitigau, F.

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

AU - Frissen, A.E.

AU - Boeriu, C.G.

PY - 2012

Y1 - 2012

N2 - Enzymatic synthesis of aromatic esters of four different sugar alcohols (xylitol, arabitol, mannitol, and sorbitol) with 3-(4-hydroxyphenyl)propionic acid was performed in organic solvent medium, using immobilized Candida antarctica lipase (Novozyme 435), and molecular sieves for control of the water content. The influence of reaction parameters on the conversion has been investigated, including reaction time, temperature, alcohol/acid molar ratio, and enzyme amount. The highest conversions (94% for xylitol, 98% for arabitol, 80% for mannitol, and 93% for sorbitol) were obtained in pure tert-butanol at 60 °C and 72 h reaction time, 0.3 alcohol/acid molar ratio, and 0.5 g/mol enzyme/substrate ratio. The isolated new sugar alcohols esters were identified by different spectral analyses. MALDI-TOF MS analysis showed the formation of monoesters, diesters, and small quantities of triesters for all investigated sugar alcohols. The catalytic efficiency of the enzyme was higher for the pentitol substrates, decreasing in the following order: arabitol > xylitol > sorbitol > mannitol. These new compounds could have interesting applications in food, pharmaceutical and cosmetic formulations

AB - Enzymatic synthesis of aromatic esters of four different sugar alcohols (xylitol, arabitol, mannitol, and sorbitol) with 3-(4-hydroxyphenyl)propionic acid was performed in organic solvent medium, using immobilized Candida antarctica lipase (Novozyme 435), and molecular sieves for control of the water content. The influence of reaction parameters on the conversion has been investigated, including reaction time, temperature, alcohol/acid molar ratio, and enzyme amount. The highest conversions (94% for xylitol, 98% for arabitol, 80% for mannitol, and 93% for sorbitol) were obtained in pure tert-butanol at 60 °C and 72 h reaction time, 0.3 alcohol/acid molar ratio, and 0.5 g/mol enzyme/substrate ratio. The isolated new sugar alcohols esters were identified by different spectral analyses. MALDI-TOF MS analysis showed the formation of monoesters, diesters, and small quantities of triesters for all investigated sugar alcohols. The catalytic efficiency of the enzyme was higher for the pentitol substrates, decreasing in the following order: arabitol > xylitol > sorbitol > mannitol. These new compounds could have interesting applications in food, pharmaceutical and cosmetic formulations

KW - lipase-catalyzed esterification

KW - candida-antarctica lipase

KW - phenolic-acids

KW - enzymatic preparation

KW - organic media

KW - esters

KW - glycosides

KW - condensation

KW - copolyesters

KW - solvents

U2 - 10.1016/j.procbio.2012.06.015

DO - 10.1016/j.procbio.2012.06.015

M3 - Article

VL - 47

SP - 1894

EP - 1902

JO - Process Biochemistry

JF - Process Biochemistry

SN - 1359-5113

IS - 12

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