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Catalytic Formation of Disulfide Bonds in Peptides by Molecularly Imprinted Microgels at Oil/Water Interfaces

Shen, Xiantao ; Huang, Chuixiu ; Shinde, Sudhirkumar ; Jagadeesan, Kishore LU ; Ekström, Simon LU ; Fritz, Emelie and Sellergren, Borje (2016) In ACS Applied Materials and Interfaces 8(44). p.30484-30491
Abstract
This work describes the preparation and investigation of molecularly imprinted polymer (MIP) microgels (MGs) stabilized Pickering emulsions (PE) for their ability to catalyze the formation of disulfide bonds in peptides at the O/W interface. The MIP MGs were synthesized via precipitation polymerization and a programmed initiator change strategy. The MIP MGs were characterized using DLS analysis, SEM measurement and optical microscopy analysis. The dry and wet MIP MGs showed a hydrodynamic diameter of 100 nm and 280 nm, respectively. Template rebinding experiment showed that the MIP MGs bound over two times more template (24 mg g-1) compared to the uptake displayed by a non-imprinted reference polymer (NIP) MG (10 mg g-1) at saturation.... (More)
This work describes the preparation and investigation of molecularly imprinted polymer (MIP) microgels (MGs) stabilized Pickering emulsions (PE) for their ability to catalyze the formation of disulfide bonds in peptides at the O/W interface. The MIP MGs were synthesized via precipitation polymerization and a programmed initiator change strategy. The MIP MGs were characterized using DLS analysis, SEM measurement and optical microscopy analysis. The dry and wet MIP MGs showed a hydrodynamic diameter of 100 nm and 280 nm, respectively. Template rebinding experiment showed that the MIP MGs bound over two times more template (24 mg g-1) compared to the uptake displayed by a non-imprinted reference polymer (NIP) MG (10 mg g-1) at saturation. Using the MIP MGs as stabilizers, catalytic oxidation systems were prepared by emulsifying the oil phase and water phase in presence of different oxidizing agents. During the cyclization, the isolation of the thiol precursors and the oxidizing reagents non-selectively decreased the formation of the byproducts, while the imprinted cavities on the MIP MGs selectively promoted the intramolecular cyclization of peptides. When I2 was used as the oxidizing agent, the MIP-PE-I2 system showed a product yield of 50 %, corresponding to a nearly two-fold increase compared to the non-imprinted polymer NIP-PE-I2 system (26 %). We believe the interfacial catalysis system presented in this work may offer significant benefits in synthetic peptide chemistry by raising productivity while suppressing the formation of by-products. (Less)
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author
; ; ; ; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
Molecularly Imprinted Polymer, Microgels, disulfide-rich cyclic peptides, Pickering emulsions, interfacial catalysis, intramolecular cyclization
in
ACS Applied Materials and Interfaces
volume
8
issue
44
pages
8 pages
publisher
The American Chemical Society (ACS)
external identifiers
  • pmid:27750005
  • scopus:84994719702
  • wos:000387737200073
ISSN
1944-8252
DOI
10.1021/acsami.6b10131
project
Robust affinity materials for applications in proteomics and diagnostics
language
English
LU publication?
yes
id
fda4f5d2-be4f-4107-875b-60fa1c37519d
date added to LUP
2016-10-24 10:58:38
date last changed
2025-03-08 18:09:28
@article{fda4f5d2-be4f-4107-875b-60fa1c37519d,
  abstract     = {{This work describes the preparation and investigation of molecularly imprinted polymer (MIP) microgels (MGs) stabilized Pickering emulsions (PE) for their ability to catalyze the formation of disulfide bonds in peptides at the O/W interface. The MIP MGs were synthesized via precipitation polymerization and a programmed initiator change strategy. The MIP MGs were characterized using DLS analysis, SEM measurement and optical microscopy analysis. The dry and wet MIP MGs showed a hydrodynamic diameter of 100 nm and 280 nm, respectively. Template rebinding experiment showed that the MIP MGs bound over two times more template (24 mg g-1) compared to the uptake displayed by a non-imprinted reference polymer (NIP) MG (10 mg g-1) at saturation. Using the MIP MGs as stabilizers, catalytic oxidation systems were prepared by emulsifying the oil phase and water phase in presence of different oxidizing agents. During the cyclization, the isolation of the thiol precursors and the oxidizing reagents non-selectively decreased the formation of the byproducts, while the imprinted cavities on the MIP MGs selectively promoted the intramolecular cyclization of peptides. When I2 was used as the oxidizing agent, the MIP-PE-I2 system showed a product yield of 50 %, corresponding to a nearly two-fold increase compared to the non-imprinted polymer NIP-PE-I2 system (26 %). We believe the interfacial catalysis system presented in this work may offer significant benefits in synthetic peptide chemistry by raising productivity while suppressing the formation of by-products.}},
  author       = {{Shen, Xiantao and Huang, Chuixiu and Shinde, Sudhirkumar and Jagadeesan, Kishore and Ekström, Simon and Fritz, Emelie and Sellergren, Borje}},
  issn         = {{1944-8252}},
  keywords     = {{Molecularly Imprinted Polymer; Microgels; disulfide-rich cyclic peptides; Pickering emulsions; interfacial catalysis; intramolecular cyclization}},
  language     = {{eng}},
  month        = {{10}},
  number       = {{44}},
  pages        = {{30484--30491}},
  publisher    = {{The American Chemical Society (ACS)}},
  series       = {{ACS Applied Materials and Interfaces}},
  title        = {{Catalytic Formation of Disulfide Bonds in Peptides by Molecularly Imprinted Microgels at Oil/Water Interfaces}},
  url          = {{http://dx.doi.org/10.1021/acsami.6b10131}},
  doi          = {{10.1021/acsami.6b10131}},
  volume       = {{8}},
  year         = {{2016}},
}