Biocatalytic synthesis of new copolymers from 3-hydroxybutyric acid and a carbohydrate lactone

Sándor Kakasi-Zsurka, Anamaria Todea, Andrada But, Cristina Paul, Carmen G. Boeriu, Corneliu Davidescu, Lajos Nagy, Ákos Kuki, S. Kéki, Francisc Péter

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

Lipase-catalyzed reaction of 3-hydroxybutyric acid with d-glucono-δ-lactone at 5:1 molar ratio and 80°C yielded a mixture of moderate molecular weight linear and cyclic oligomers. The most efficient biocatalyst, Candida antarctica B lipase (Novozyme 435), allowed the synthesis of new oligomeric compounds with ring-opened gluconolactone units included in the oligomeric chain, without previous derivatization of the sugar, or activation of the acid monomer. The reaction medium nature had an important influence on the product composition. Although the main copolymer amount was synthesized in tert-butanol/dimethylsulfoxide medium, the highest polymerization degrees, up to 9 for the copolymer, and 10 for the 3-hydroxybutyric acid homopolymer co-product, were achieved in solventless conditions.

Original languageEnglish
Pages (from-to)22-28
Number of pages7
JournalJournal of Molecular Catalysis B: Enzymatic
Volume71
Issue number1-2
DOIs
Publication statusPublished - Aug 2011

Fingerprint

3-Hydroxybutyric Acid
Lactones
Carbohydrates
Copolymers
tert-Butyl Alcohol
Lipases
Acids
Dimethyl Sulfoxide
Homopolymerization
Lipase
Oligomers
Sugars
Polymerization
Biocatalysts
Candida
Monomers
Molecular Weight
Chemical activation
Molecular weight
Butenes

Keywords

  • 3-Hydroxybutyric acid
  • Biocatalysis
  • Biopolymers
  • Gluconolactone
  • Lipase

ASJC Scopus subject areas

  • Biochemistry
  • Bioengineering
  • Catalysis
  • Process Chemistry and Technology

Cite this

Kakasi-Zsurka, S., Todea, A., But, A., Paul, C., Boeriu, C. G., Davidescu, C., ... Péter, F. (2011). Biocatalytic synthesis of new copolymers from 3-hydroxybutyric acid and a carbohydrate lactone. Journal of Molecular Catalysis B: Enzymatic, 71(1-2), 22-28. https://doi.org/10.1016/j.molcatb.2011.03.004

Biocatalytic synthesis of new copolymers from 3-hydroxybutyric acid and a carbohydrate lactone. / Kakasi-Zsurka, Sándor; Todea, Anamaria; But, Andrada; Paul, Cristina; Boeriu, Carmen G.; Davidescu, Corneliu; Nagy, Lajos; Kuki, Ákos; Kéki, S.; Péter, Francisc.

In: Journal of Molecular Catalysis B: Enzymatic, Vol. 71, No. 1-2, 08.2011, p. 22-28.

Research output: Contribution to journalArticle

Kakasi-Zsurka, S, Todea, A, But, A, Paul, C, Boeriu, CG, Davidescu, C, Nagy, L, Kuki, Á, Kéki, S & Péter, F 2011, 'Biocatalytic synthesis of new copolymers from 3-hydroxybutyric acid and a carbohydrate lactone', Journal of Molecular Catalysis B: Enzymatic, vol. 71, no. 1-2, pp. 22-28. https://doi.org/10.1016/j.molcatb.2011.03.004
Kakasi-Zsurka, Sándor ; Todea, Anamaria ; But, Andrada ; Paul, Cristina ; Boeriu, Carmen G. ; Davidescu, Corneliu ; Nagy, Lajos ; Kuki, Ákos ; Kéki, S. ; Péter, Francisc. / Biocatalytic synthesis of new copolymers from 3-hydroxybutyric acid and a carbohydrate lactone. In: Journal of Molecular Catalysis B: Enzymatic. 2011 ; Vol. 71, No. 1-2. pp. 22-28.
@article{f4fbeb0fc5574cafa06d540b0e2347ad,
title = "Biocatalytic synthesis of new copolymers from 3-hydroxybutyric acid and a carbohydrate lactone",
abstract = "Lipase-catalyzed reaction of 3-hydroxybutyric acid with d-glucono-δ-lactone at 5:1 molar ratio and 80°C yielded a mixture of moderate molecular weight linear and cyclic oligomers. The most efficient biocatalyst, Candida antarctica B lipase (Novozyme 435), allowed the synthesis of new oligomeric compounds with ring-opened gluconolactone units included in the oligomeric chain, without previous derivatization of the sugar, or activation of the acid monomer. The reaction medium nature had an important influence on the product composition. Although the main copolymer amount was synthesized in tert-butanol/dimethylsulfoxide medium, the highest polymerization degrees, up to 9 for the copolymer, and 10 for the 3-hydroxybutyric acid homopolymer co-product, were achieved in solventless conditions.",
keywords = "3-Hydroxybutyric acid, Biocatalysis, Biopolymers, Gluconolactone, Lipase",
author = "S{\'a}ndor Kakasi-Zsurka and Anamaria Todea and Andrada But and Cristina Paul and Boeriu, {Carmen G.} and Corneliu Davidescu and Lajos Nagy and {\'A}kos Kuki and S. K{\'e}ki and Francisc P{\'e}ter",
year = "2011",
month = "8",
doi = "10.1016/j.molcatb.2011.03.004",
language = "English",
volume = "71",
pages = "22--28",
journal = "Journal of Molecular Catalysis - B Enzymatic",
issn = "1381-1177",
publisher = "Elsevier",
number = "1-2",

}

TY - JOUR

T1 - Biocatalytic synthesis of new copolymers from 3-hydroxybutyric acid and a carbohydrate lactone

AU - Kakasi-Zsurka, Sándor

AU - Todea, Anamaria

AU - But, Andrada

AU - Paul, Cristina

AU - Boeriu, Carmen G.

AU - Davidescu, Corneliu

AU - Nagy, Lajos

AU - Kuki, Ákos

AU - Kéki, S.

AU - Péter, Francisc

PY - 2011/8

Y1 - 2011/8

N2 - Lipase-catalyzed reaction of 3-hydroxybutyric acid with d-glucono-δ-lactone at 5:1 molar ratio and 80°C yielded a mixture of moderate molecular weight linear and cyclic oligomers. The most efficient biocatalyst, Candida antarctica B lipase (Novozyme 435), allowed the synthesis of new oligomeric compounds with ring-opened gluconolactone units included in the oligomeric chain, without previous derivatization of the sugar, or activation of the acid monomer. The reaction medium nature had an important influence on the product composition. Although the main copolymer amount was synthesized in tert-butanol/dimethylsulfoxide medium, the highest polymerization degrees, up to 9 for the copolymer, and 10 for the 3-hydroxybutyric acid homopolymer co-product, were achieved in solventless conditions.

AB - Lipase-catalyzed reaction of 3-hydroxybutyric acid with d-glucono-δ-lactone at 5:1 molar ratio and 80°C yielded a mixture of moderate molecular weight linear and cyclic oligomers. The most efficient biocatalyst, Candida antarctica B lipase (Novozyme 435), allowed the synthesis of new oligomeric compounds with ring-opened gluconolactone units included in the oligomeric chain, without previous derivatization of the sugar, or activation of the acid monomer. The reaction medium nature had an important influence on the product composition. Although the main copolymer amount was synthesized in tert-butanol/dimethylsulfoxide medium, the highest polymerization degrees, up to 9 for the copolymer, and 10 for the 3-hydroxybutyric acid homopolymer co-product, were achieved in solventless conditions.

KW - 3-Hydroxybutyric acid

KW - Biocatalysis

KW - Biopolymers

KW - Gluconolactone

KW - Lipase

UR - http://www.scopus.com/inward/record.url?scp=79956072621&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=79956072621&partnerID=8YFLogxK

U2 - 10.1016/j.molcatb.2011.03.004

DO - 10.1016/j.molcatb.2011.03.004

M3 - Article

VL - 71

SP - 22

EP - 28

JO - Journal of Molecular Catalysis - B Enzymatic

JF - Journal of Molecular Catalysis - B Enzymatic

SN - 1381-1177

IS - 1-2

ER -