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Synthesis, molecular docking simulation and enzymatic degradation of AB-type indole-based polyesters with improved thermal properties

Wang, Ping LU ; Linares-Pastén, Javier LU orcid and Zhang, Baozhong LU (2020) In Biomacromolecules 21(3). p.1078-1090
Abstract

We report the facile synthesis of a series of indole-based hydroxyl-carboxylate (AB-type) monomers by a one-step procedure. These monomers were successfully polymerized by melt-polycondensation to yield AB-type polyesters with a varied number of flexible methylene units in the backbones. These indole-based AB-polyesters showed decent thermal stability according to the TGA results (onset thermal degradation temperature >330 °C), and their glass transition temperatures are dependent on the length of the methylene bridge (Tg ~ 62-102 °C) according to the DSC results. Furthermore, DSC and WAXD measurements revealed that these polymers did not crystalize from melt, but the ones with flexible structures could crystalize from solution.... (More)

We report the facile synthesis of a series of indole-based hydroxyl-carboxylate (AB-type) monomers by a one-step procedure. These monomers were successfully polymerized by melt-polycondensation to yield AB-type polyesters with a varied number of flexible methylene units in the backbones. These indole-based AB-polyesters showed decent thermal stability according to the TGA results (onset thermal degradation temperature >330 °C), and their glass transition temperatures are dependent on the length of the methylene bridge (Tg ~ 62-102 °C) according to the DSC results. Furthermore, DSC and WAXD measurements revealed that these polymers did not crystalize from melt, but the ones with flexible structures could crystalize from solution. Molecular docking simulations showed favorable interactions between indole-based polyester and polyethylene terephthalate hydrolase (PETase) from Idonella sakaiensis. This was corroborated by the experimental results, which indicated that the PETase enzyme has degrading activity on the indole-based AB polyesters except for the one with the highest degree of crystallinity.

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author
; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Biomacromolecules
volume
21
issue
3
pages
14 pages
publisher
The American Chemical Society (ACS)
external identifiers
  • scopus:85081744042
  • pmid:31951388
ISSN
1526-4602
DOI
10.1021/acs.biomac.9b01399
project
STEPS – Sustainable Plastics and Transition Pathways, Phase 1
language
English
LU publication?
yes
id
d7c74d7e-a29d-46dc-9a73-981c69580142
date added to LUP
2020-01-31 10:32:16
date last changed
2024-06-12 08:22:52
@article{d7c74d7e-a29d-46dc-9a73-981c69580142,
  abstract     = {{<p>We report the facile synthesis of a series of indole-based hydroxyl-carboxylate (AB-type) monomers by a one-step procedure. These monomers were successfully polymerized by melt-polycondensation to yield AB-type polyesters with a varied number of flexible methylene units in the backbones. These indole-based AB-polyesters showed decent thermal stability according to the TGA results (onset thermal degradation temperature &gt;330 °C), and their glass transition temperatures are dependent on the length of the methylene bridge (Tg ~ 62-102 °C) according to the DSC results. Furthermore, DSC and WAXD measurements revealed that these polymers did not crystalize from melt, but the ones with flexible structures could crystalize from solution. Molecular docking simulations showed favorable interactions between indole-based polyester and polyethylene terephthalate hydrolase (PETase) from Idonella sakaiensis. This was corroborated by the experimental results, which indicated that the PETase enzyme has degrading activity on the indole-based AB polyesters except for the one with the highest degree of crystallinity.</p>}},
  author       = {{Wang, Ping and Linares-Pastén, Javier and Zhang, Baozhong}},
  issn         = {{1526-4602}},
  language     = {{eng}},
  month        = {{03}},
  number       = {{3}},
  pages        = {{1078--1090}},
  publisher    = {{The American Chemical Society (ACS)}},
  series       = {{Biomacromolecules}},
  title        = {{Synthesis, molecular docking simulation and enzymatic degradation of AB-type indole-based polyesters with improved thermal properties}},
  url          = {{http://dx.doi.org/10.1021/acs.biomac.9b01399}},
  doi          = {{10.1021/acs.biomac.9b01399}},
  volume       = {{21}},
  year         = {{2020}},
}