Biocatalytic Synthesis of Maltodextrin-Based Acrylates from Starch and alpha-Cyclodextrin

Wouter M. J. Kloosterman; Gerda Spoelstra-van Dijk; Katja Loos

doi:10.1002/mabi.201400091

Biocatalytic Synthesis of Maltodextrin-Based Acrylates from Starch and alpha-Cyclodextrin

Wouter M. J. Kloosterman, Gerda Spoelstra-van Dijk, Katja Loos^*

^*Corresponding author for this work

Macromolecular Chemistry and New Polymeric Materials

Research output: Contribution to journal › Article › Academic › peer-review

10 Citations (Scopus)

Abstract

Novel 2-(beta-maltooligooxy)-ethyl (meth) acrylate monomers are successfully synthesized by CGTase from Bacillus macerans catalyzed coupling of 2-(beta-glucosyloxy)-ethyl acrylate and methacrylate with a-cyclodextrin or starch. HPLC-UV analysis shows that the CGTase catalyzed reaction yields 2-(beta-maltooligooxy)-ethyl acrylates with 1 to 15 glucopyranosyl units. H-1 NMR spectroscopy reveals that the beta-linkage in the acceptor molecule is preserved during the CGTase catalyzed coupling reaction, whereas the newly introduced glucose units are attached by alpha-(1,4)-glycosidic linkages. The synthesized 2-(beta-maltooligooxy)-ethyl acrylate monomers are successfully polymerized by aqueous free radical polymerization to yield the comb-shaped glycopolymer poly(2-(beta-maltooligooxy)-ethyl acrylate).

Original language	English
Pages (from-to)	1268-1279
Number of pages	12
Journal	Macromolecular Bioscience
Volume	14
Issue number	9
DOIs	https://doi.org/10.1002/mabi.201400091
Publication status	Published - Sept-2014

Keywords

acrylates
biocatalytic
cyclodextrin
glucosyl transferase
polyglucosides
MACERANS CYCLOMALTODEXTRIN GLUCANYLTRANSFERASE
GLYCOGEN BRANCHING ENZYME
COIL BLOCK-COPOLYMERS
TRANSGLYCOSYLATION REACTIONS
DEINOCOCCUS-GEOTHERMALIS
POTATO PHOSPHORYLASE
GLUCANOTRANSFERASE
GLYCOSYLTRANSFERASE
AMYLOSE
MALTOOLIGOSACCHARIDES

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@article{a8763f5e578b47beb355b57942df1547,

title = "Biocatalytic Synthesis of Maltodextrin-Based Acrylates from Starch and alpha-Cyclodextrin",

abstract = "Novel 2-(beta-maltooligooxy)-ethyl (meth) acrylate monomers are successfully synthesized by CGTase from Bacillus macerans catalyzed coupling of 2-(beta-glucosyloxy)-ethyl acrylate and methacrylate with a-cyclodextrin or starch. HPLC-UV analysis shows that the CGTase catalyzed reaction yields 2-(beta-maltooligooxy)-ethyl acrylates with 1 to 15 glucopyranosyl units. H-1 NMR spectroscopy reveals that the beta-linkage in the acceptor molecule is preserved during the CGTase catalyzed coupling reaction, whereas the newly introduced glucose units are attached by alpha-(1,4)-glycosidic linkages. The synthesized 2-(beta-maltooligooxy)-ethyl acrylate monomers are successfully polymerized by aqueous free radical polymerization to yield the comb-shaped glycopolymer poly(2-(beta-maltooligooxy)-ethyl acrylate).",

keywords = "acrylates, biocatalytic, cyclodextrin, glucosyl transferase, polyglucosides, MACERANS CYCLOMALTODEXTRIN GLUCANYLTRANSFERASE, GLYCOGEN BRANCHING ENZYME, COIL BLOCK-COPOLYMERS, TRANSGLYCOSYLATION REACTIONS, DEINOCOCCUS-GEOTHERMALIS, POTATO PHOSPHORYLASE, GLUCANOTRANSFERASE, GLYCOSYLTRANSFERASE, AMYLOSE, MALTOOLIGOSACCHARIDES",

author = "Kloosterman, {Wouter M. J.} and {Spoelstra-van Dijk}, Gerda and Katja Loos",

year = "2014",

month = sep,

doi = "10.1002/mabi.201400091",

language = "English",

volume = "14",

pages = "1268--1279",

journal = "Macromolecular Bioscience",

issn = "1616-5187",

publisher = "WILEY-V C H VERLAG GMBH",

number = "9",

}

TY - JOUR

T1 - Biocatalytic Synthesis of Maltodextrin-Based Acrylates from Starch and alpha-Cyclodextrin

AU - Kloosterman, Wouter M. J.

AU - Spoelstra-van Dijk, Gerda

AU - Loos, Katja

PY - 2014/9

Y1 - 2014/9

N2 - Novel 2-(beta-maltooligooxy)-ethyl (meth) acrylate monomers are successfully synthesized by CGTase from Bacillus macerans catalyzed coupling of 2-(beta-glucosyloxy)-ethyl acrylate and methacrylate with a-cyclodextrin or starch. HPLC-UV analysis shows that the CGTase catalyzed reaction yields 2-(beta-maltooligooxy)-ethyl acrylates with 1 to 15 glucopyranosyl units. H-1 NMR spectroscopy reveals that the beta-linkage in the acceptor molecule is preserved during the CGTase catalyzed coupling reaction, whereas the newly introduced glucose units are attached by alpha-(1,4)-glycosidic linkages. The synthesized 2-(beta-maltooligooxy)-ethyl acrylate monomers are successfully polymerized by aqueous free radical polymerization to yield the comb-shaped glycopolymer poly(2-(beta-maltooligooxy)-ethyl acrylate).

AB - Novel 2-(beta-maltooligooxy)-ethyl (meth) acrylate monomers are successfully synthesized by CGTase from Bacillus macerans catalyzed coupling of 2-(beta-glucosyloxy)-ethyl acrylate and methacrylate with a-cyclodextrin or starch. HPLC-UV analysis shows that the CGTase catalyzed reaction yields 2-(beta-maltooligooxy)-ethyl acrylates with 1 to 15 glucopyranosyl units. H-1 NMR spectroscopy reveals that the beta-linkage in the acceptor molecule is preserved during the CGTase catalyzed coupling reaction, whereas the newly introduced glucose units are attached by alpha-(1,4)-glycosidic linkages. The synthesized 2-(beta-maltooligooxy)-ethyl acrylate monomers are successfully polymerized by aqueous free radical polymerization to yield the comb-shaped glycopolymer poly(2-(beta-maltooligooxy)-ethyl acrylate).

KW - acrylates

KW - biocatalytic

KW - cyclodextrin

KW - glucosyl transferase

KW - polyglucosides

KW - MACERANS CYCLOMALTODEXTRIN GLUCANYLTRANSFERASE

KW - GLYCOGEN BRANCHING ENZYME

KW - COIL BLOCK-COPOLYMERS

KW - TRANSGLYCOSYLATION REACTIONS

KW - DEINOCOCCUS-GEOTHERMALIS

KW - POTATO PHOSPHORYLASE

KW - GLUCANOTRANSFERASE

KW - GLYCOSYLTRANSFERASE

KW - AMYLOSE

KW - MALTOOLIGOSACCHARIDES

U2 - 10.1002/mabi.201400091

DO - 10.1002/mabi.201400091

M3 - Article

SN - 1616-5187

VL - 14

SP - 1268

EP - 1279

JO - Macromolecular Bioscience

JF - Macromolecular Bioscience

IS - 9

ER -

Biocatalytic Synthesis of Maltodextrin-Based Acrylates from Starch and alpha-Cyclodextrin

Abstract

Keywords

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