Lipase catalyzed synthesis of aromatic esters of sugar alcohols

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

Research output: Contribution to journalArticleAcademicpeer-review

4 Citations (Scopus)

Abstract

Commercially available lipases (Candida antarctica lipase B, Novozyme 435, Thermomyces lanuginosus lipase, and Lipozyme TL IM), as well as sol-gel immobilized lipases, have been screened for their ability to acylate regioselectively xylitol, sorbitol, and mannitol with a phenolic ester in a binary mixture of t-butanol and dimethylsulfoxide. HPLC and MALDI-TOF MS analysis revealed the exclusive formation of monoesters for all studied sugar alcohols. The lipases immobilized by the sol-gel entrapment method proved to be efficient catalysts, leading to high conversions (up to 60%) in the investigated acylation reactions. From a sequence of silane precursors with different nonhydrolyzable groups in their structure, the presence of octyl and i-butyl group was most beneficial for the catalytic activity of sol-gel entrapped lipases in the studied process.
Original languageEnglish
Pages (from-to)484-489
JournalWorld Academy of Science, Engineering and Technology
Volume76
Publication statusPublished - 2011

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Sugar Alcohols
Lipase
Esters
Sol-gels
tert-Butyl Alcohol
Xylitol
Silanes
Acylation
Sorbitol
Mannitol
Binary mixtures
Dimethyl Sulfoxide
Sol-gel process
Catalyst activity
Catalysts

Cite this

@article{2c44bc8b67c645b293ae3b6ffd4bc2b0,
title = "Lipase catalyzed synthesis of aromatic esters of sugar alcohols",
abstract = "Commercially available lipases (Candida antarctica lipase B, Novozyme 435, Thermomyces lanuginosus lipase, and Lipozyme TL IM), as well as sol-gel immobilized lipases, have been screened for their ability to acylate regioselectively xylitol, sorbitol, and mannitol with a phenolic ester in a binary mixture of t-butanol and dimethylsulfoxide. HPLC and MALDI-TOF MS analysis revealed the exclusive formation of monoesters for all studied sugar alcohols. The lipases immobilized by the sol-gel entrapment method proved to be efficient catalysts, leading to high conversions (up to 60{\%}) in the investigated acylation reactions. From a sequence of silane precursors with different nonhydrolyzable groups in their structure, the presence of octyl and i-butyl group was most beneficial for the catalytic activity of sol-gel entrapped lipases in the studied process.",
author = "R. Croitoru and {van den Broek}, L.A.M. and A.E. Frissen and C.M. Davidescu and F. Peter and C.G. Boeriu",
year = "2011",
language = "English",
volume = "76",
pages = "484--489",
journal = "World Academy of Science, Engineering and Technology",
issn = "2070-3740",

}

Lipase catalyzed synthesis of aromatic esters of sugar alcohols. / Croitoru, R.; van den Broek, L.A.M.; Frissen, A.E.; Davidescu, C.M.; Peter, F.; Boeriu, C.G.

In: World Academy of Science, Engineering and Technology, Vol. 76, 2011, p. 484-489.

Research output: Contribution to journalArticleAcademicpeer-review

TY - JOUR

T1 - Lipase catalyzed synthesis of aromatic esters of sugar alcohols

AU - Croitoru, R.

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

AU - Frissen, A.E.

AU - Davidescu, C.M.

AU - Peter, F.

AU - Boeriu, C.G.

PY - 2011

Y1 - 2011

N2 - Commercially available lipases (Candida antarctica lipase B, Novozyme 435, Thermomyces lanuginosus lipase, and Lipozyme TL IM), as well as sol-gel immobilized lipases, have been screened for their ability to acylate regioselectively xylitol, sorbitol, and mannitol with a phenolic ester in a binary mixture of t-butanol and dimethylsulfoxide. HPLC and MALDI-TOF MS analysis revealed the exclusive formation of monoesters for all studied sugar alcohols. The lipases immobilized by the sol-gel entrapment method proved to be efficient catalysts, leading to high conversions (up to 60%) in the investigated acylation reactions. From a sequence of silane precursors with different nonhydrolyzable groups in their structure, the presence of octyl and i-butyl group was most beneficial for the catalytic activity of sol-gel entrapped lipases in the studied process.

AB - Commercially available lipases (Candida antarctica lipase B, Novozyme 435, Thermomyces lanuginosus lipase, and Lipozyme TL IM), as well as sol-gel immobilized lipases, have been screened for their ability to acylate regioselectively xylitol, sorbitol, and mannitol with a phenolic ester in a binary mixture of t-butanol and dimethylsulfoxide. HPLC and MALDI-TOF MS analysis revealed the exclusive formation of monoesters for all studied sugar alcohols. The lipases immobilized by the sol-gel entrapment method proved to be efficient catalysts, leading to high conversions (up to 60%) in the investigated acylation reactions. From a sequence of silane precursors with different nonhydrolyzable groups in their structure, the presence of octyl and i-butyl group was most beneficial for the catalytic activity of sol-gel entrapped lipases in the studied process.

M3 - Article

VL - 76

SP - 484

EP - 489

JO - World Academy of Science, Engineering and Technology

JF - World Academy of Science, Engineering and Technology

SN - 2070-3740

ER -