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Catalytic Formation of Disulfide Bonds in Peptides by Molecularly Imprinted Microgels at Oil/Water Interfaces
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- Shen, Xiantao (author)
- Malmö högskola,Malmö University,Key Laboratory of Environment and Health, Ministry of Education & Ministry of Environmental Protection, State Key Laboratory of Environmental Health (Incubation), School of Public Health, Tongji Medical College, Huazhong University of Science and Technology, Hangkong Road #13, Wuhan, Hubei 430030, China; G&T Septech AS, P.O. Box 33, 1917 Ytre Enebakk, Norway,G&T Septech AS,Institutionen för biomedicinsk vetenskap (BMV),Biofilms Research Center for Biointerfaces
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- Huang, Chuixiu (author)
- Malmö högskola,Malmö University,School of Pharmacy, University of Oslo, P.O. Box 1068, 0316 Blindern Oslo, Norway; G&T Septech AS, P.O. Box 33, 1917 Ytre Enebakk, Norway,University of Oslo,Institutionen för biomedicinsk vetenskap (BMV),Biofilms Research Center for Biointerfaces
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- Shinde, Sudhirkumar (author)
- Malmö högskola,Malmö University,Institutionen för biomedicinsk vetenskap (BMV),Biofilms Research Center for Biointerfaces
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- Malmö University Key Laboratory of Environment and Health, Ministry of Education & Ministry of Environmental Protection, State Key Laboratory of Environmental Health (Incubation), School of Public Health, Tongji Medical College, Huazhong University of Science and Technology, Hangkong Road #13, Wuhan, Hubei 430030, China; G&T Septech AS, PO. Box 33, 1917 Ytre Enebakk, Norway (creator_code:org_t)
- 2016-10-26
- 2016
- English 8 s.
- In: ACS Applied Materials and Interfaces. - : American Chemical Society (ACS). - 1944-8252 .- 1944-8244. ; 8:44, s. 30484-30491
- Journal article (peer-reviewed)
Abstract
Subject headings
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- 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.
Subject headings
- TEKNIK OCH TEKNOLOGIER -- Materialteknik (hsv//swe)
- ENGINEERING AND TECHNOLOGY -- Materials Engineering (hsv//eng)
Keyword
- Molecularly Imprinted Polymer
- Microgels
- disulfide-rich cyclic peptides
- Pickering emulsions
- interfacial catalysis
- intramolecular cyclization
- disulfide-rich cyclic peptides
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- art (subject category)
- ref (subject category)
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