Enzyme-Catalyzed Polymerization of Beta-alanine Esters, A Sustainable Route Towards the Formation of Poly-Beta-alanine

P. Steunenberg; M. Uiterweerd; M. Sijm; E.L. Scott; H. Zuilhof; J.P.M. Sanders; M.C.R. Franssen

doi:10.2174/1385272811317070004

Enzyme-Catalyzed Polymerization of Beta-alanine Esters, A Sustainable Route Towards the Formation of Poly-Beta-alanine

P. Steunenberg, M. Uiterweerd, M. Sijm, E.L. Scott, H. Zuilhof, J.P.M. Sanders, M.C.R. Franssen

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

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Abstract

The synthesis of poly-ß-alanine by a lipase catalyzed polycondensation reaction between ß-alanine esters is reported. The effect of different solvents, reaction temperatures and substrate/enzyme concentrations on polymer yield and degree of polymerization (DP) was determined. Also the effect of methyl substituents at the a and ß position of ß-alanine was studied. Cross-Linked Enzyme Aggregates (CLEA) of Candida antarctica lipase B converted ß-alanine esters into polymers in high yield (up to 90%) and with high (DP) (up to 53 units). Optimum results were obtained when methyl esters are used in methyl tert-butyl ether (MTBE) as the solvent, at 50°C for 16 h.

Original language	English
Pages (from-to)	682-690
Journal	Current Organic Chemistry
Volume	17
Issue number	7
DOIs	https://doi.org/10.2174/1385272811317070004
Publication status	Published - 2013

Keywords

nitrogen-containing chemicals
ring-opening polymerization
amino-acids
organic-solvents
biobased production
peptides
lactams
lipases
biotransformations
esterification

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title = "Enzyme-Catalyzed Polymerization of Beta-alanine Esters, A Sustainable Route Towards the Formation of Poly-Beta-alanine",

abstract = "The synthesis of poly-{\ss}-alanine by a lipase catalyzed polycondensation reaction between {\ss}-alanine esters is reported. The effect of different solvents, reaction temperatures and substrate/enzyme concentrations on polymer yield and degree of polymerization (DP) was determined. Also the effect of methyl substituents at the a and {\ss} position of {\ss}-alanine was studied. Cross-Linked Enzyme Aggregates (CLEA) of Candida antarctica lipase B converted {\ss}-alanine esters into polymers in high yield (up to 90%) and with high (DP) (up to 53 units). Optimum results were obtained when methyl esters are used in methyl tert-butyl ether (MTBE) as the solvent, at 50°C for 16 h.",

keywords = "nitrogen-containing chemicals, ring-opening polymerization, amino-acids, organic-solvents, biobased production, peptides, lactams, lipases, biotransformations, esterification",

author = "P. Steunenberg and M. Uiterweerd and M. Sijm and E.L. Scott and H. Zuilhof and J.P.M. Sanders and M.C.R. Franssen",

year = "2013",

doi = "10.2174/1385272811317070004",

language = "English",

volume = "17",

pages = "682--690",

journal = "Current Organic Chemistry",

issn = "1385-2728",

publisher = "Bentham Science Publishers",

number = "7",

}

TY - JOUR

T1 - Enzyme-Catalyzed Polymerization of Beta-alanine Esters, A Sustainable Route Towards the Formation of Poly-Beta-alanine

AU - Steunenberg, P.

AU - Uiterweerd, M.

AU - Sijm, M.

AU - Scott, E.L.

AU - Zuilhof, H.

AU - Sanders, J.P.M.

AU - Franssen, M.C.R.

PY - 2013

Y1 - 2013

N2 - The synthesis of poly-ß-alanine by a lipase catalyzed polycondensation reaction between ß-alanine esters is reported. The effect of different solvents, reaction temperatures and substrate/enzyme concentrations on polymer yield and degree of polymerization (DP) was determined. Also the effect of methyl substituents at the a and ß position of ß-alanine was studied. Cross-Linked Enzyme Aggregates (CLEA) of Candida antarctica lipase B converted ß-alanine esters into polymers in high yield (up to 90%) and with high (DP) (up to 53 units). Optimum results were obtained when methyl esters are used in methyl tert-butyl ether (MTBE) as the solvent, at 50°C for 16 h.

AB - The synthesis of poly-ß-alanine by a lipase catalyzed polycondensation reaction between ß-alanine esters is reported. The effect of different solvents, reaction temperatures and substrate/enzyme concentrations on polymer yield and degree of polymerization (DP) was determined. Also the effect of methyl substituents at the a and ß position of ß-alanine was studied. Cross-Linked Enzyme Aggregates (CLEA) of Candida antarctica lipase B converted ß-alanine esters into polymers in high yield (up to 90%) and with high (DP) (up to 53 units). Optimum results were obtained when methyl esters are used in methyl tert-butyl ether (MTBE) as the solvent, at 50°C for 16 h.

KW - nitrogen-containing chemicals

KW - ring-opening polymerization

KW - amino-acids

KW - organic-solvents

KW - biobased production

KW - peptides

KW - lactams

KW - lipases

KW - biotransformations

KW - esterification

U2 - 10.2174/1385272811317070004

DO - 10.2174/1385272811317070004

M3 - Article

SN - 1385-2728

VL - 17

SP - 682

EP - 690

JO - Current Organic Chemistry

JF - Current Organic Chemistry

IS - 7

ER -

Enzyme-Catalyzed Polymerization of Beta-alanine Esters, A Sustainable Route Towards the Formation of Poly-Beta-alanine

Abstract

Keywords

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