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Enzymatic Synthesis of Polyesters via Ring-Opening Polymerization

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Enzyme-Catalyzed Synthesis of Polymers

Part of the book series: Advances in Polymer Science ((POLYMER,volume 194))

Abstract

An enzyme can act as a powerful catalyst for the production and chemical recycling of green and sustainable polymers via a ring-opening polymerization. Also, enzymes will provide versatile synthetic tools for regio- and enantioselective polymerizations. In this article, lipase-catalyzed ring-opening polymerization and copolymerization of small-sized four-membered lactones to macrolides and cyclic oligomers having a molecular weight of a few hundred into high-molecular-weight polyesters, ring-opening polymerization of substitutedβunsubstituted cyclic carbonates and cyclic phosphates into polycarbonates and polyphosphates, and the mechanism of lipase-catalyzed ring-opening polymerization of lactones and cyclic carbonates are reviewed. Also degradative transformation of polyesters and polycarbonates into the corresponding cyclic oligomers as repetitive chemical recycling and trends for enzymatic ring-opening polymerization and degradation are described.

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Abbreviations

β-BL:

β-butyrolactone

BTMC:

5-benzyloxy-1,3-dioxan-2-one

CCL:

lipase from Candida cylindracea

CL:

6-hydroxyhexanoate

ε-CL:

ε-caprolactone

scCO2:

supercritical carbon dioxide

DCL:

dicaprolactone

DDL:

12-dodecanolide

DP:

degree of polymerization

DTC:

5,5-dimethyl-trimethylene carbonate

EM:

enzyme-activated monomer

EEP:

ethyl ethylene phosphate

(R,S)-4-EtCL:

4-ethyl-caprolactone

3HB:

3-hydroxybutanoate

K m :

Michaelis constant

lipase CA:

immobilized lipase from Candida antarctica

MBC:

5-methyl-5-benzyloxycarbonyl-1,3-dioxan-2-one

(R,S)-4-MeCL:

racemic 4-methyl-caprolactone

M n :

number-average molecular weight

MOHEL:

3-methyl-4-oxa-6-hexanolides

3MP:

3-mercaptopropionic acid

MPL:

α-methyl-β-propiolactone

M w :

weight-average molecular weight

11MU:

11-mercaptoundecanoic acid

PBA:

poly(butylene adipate)

PCL:

poly(ε-caprolactone)

PDL:

15-pentadecanolide

PDLLA:

poly(DL-lactic acid)

PEG:

poly(ethylene glycol)

PHB:

poly(3-hydroxybutanoate)

PHA:

poly(R-3-hydroxyalkanoate)

PhaZAfa:

PHB depolymerase from Alcaligenes faecalis T1

PLA:

poly(lactic acid)

PLLA:

poly(L-lactic acid)

β-PL:

β-propiolactone

PPL:

porcine pancrease lipase

SBD:

substrate binding domain

SL:

sophorolipid

T m :

glass transition temperature

TMC:

trimethylene carbonate (1,3-dioxan-2-one)

UDL:

11-undecanolide

V max:

maximal velocity

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  1. Faculty of Science and Technology, Keio University, 3-14-1, Hiyoshi, Kohoku-ku, 223-8522, Yokohama, Japan

    Shuichi Matsumura

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Shiro Kobayashi Helmut Ritter David Kaplan

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Matsumura, S. Enzymatic Synthesis of Polyesters via Ring-Opening Polymerization. In: Kobayashi, S., Ritter, H., Kaplan, D. (eds) Enzyme-Catalyzed Synthesis of Polymers. Advances in Polymer Science, vol 194. Springer, Berlin, Heidelberg. https://doi.org/10.1007/12_030

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