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Short One-Pot Chemo-Enzymatic Synthesis of L-Lysine and L-Alanine Diblock Co-Oligopeptides
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Polymer Technology.
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Polymer Technology.ORCID iD: 0000-0002-1922-128X
2014 (English)In: Biomacromolecules, ISSN 1525-7797, E-ISSN 1526-4602, Vol. 15, no 3, 735-743 p.Article in journal (Refereed) Published
Abstract [en]

Amphiphilic diblock co-oligopeptides are interesting and functional macromolecular materials for biomedical applications because of their self-assembling properties. Here, we developed a synthesis method for diblock co-oligopeptides by using chemo-enzymatic polymerization, which was a relatively short (30 min) and efficient reaction (over 40% yield). Block and random oligo(L-lysine-co-L-alanine) [oligo(Lys-co-Ala)] were synthesized using activated papain as enzymatic catalyst. The reaction time was optimized according to kinetic studies of oligo(L-alanine) and oligo(L-lysine). Using H-1 NMR spectroscopy and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry, we confirmed that diblock and random co-oligopeptides were synthesized. Optical microscopy further revealed differences in the crystalline morphology between random and block co-oligopeptides. Plate-like, hexagonal, and hollow crystals were formed due to the strong impact of the monomer distribution and pH of the solution. The different crystalline structures open up interesting possibilities to form materials for both tissue engineering and controlled drug/gene delivery systems.

Place, publisher, year, edition, pages
American Chemical Society (ACS), 2014. Vol. 15, no 3, 735-743 p.
Keyword [en]
Biomedical applications, Chemo-enzymatic synthesis, Crystalline morphologies, Crystalline structure, Drug/gene delivery, H NMR spectroscopy, Matrix-assisted laser desorption/ionization-time-of-flight mass spectrometry, Self-assembling properties
National Category
Polymer Chemistry Biochemistry and Molecular Biology Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-144372DOI: 10.1021/bm4015254ISI: 000332756600005Scopus ID: 2-s2.0-84896752024OAI: oai:DiVA.org:kth-144372DiVA: diva2:713283
Note

QC 20140422

Available from: 2014-04-22 Created: 2014-04-22 Last updated: 2017-12-11Bibliographically approved
In thesis
1. Synthesis of degradable aliphatic polyesters: strategies to tailor the polymer microstructure
Open this publication in new window or tab >>Synthesis of degradable aliphatic polyesters: strategies to tailor the polymer microstructure
2018 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

Key factors for successful tissue engineering are the synthesis and design of the scaffold materials. Aliphatic polyesters have been studied and often used as scaffold materials for tissue engineering. However, their lack of biological cues and degradation under high-temperature processing (e.g., 3D printing) are a limitation. In this thesis, different synthesis strategies are presented which has the potential to improve the performance of aliphatic polyesters as scaffolds for tissue regeneration.

To stimulate interactions between exogenous materials and the surrounding tissue, two different strategies were applied. Either, by designing a two component system in which the different degradation profiles of the polymers allow for sequential release of growth factors. Or, by peptide functionalization of an aliphatic polyester chain using template-assisted chemo-enzymatic synthesis. The results from the studies were successful. A hierarchical system was obtained in which the poly(L-lactide-co-glycolide)-graft-poly(ethylene glycol) methyl ether (PLGA-g-MPEG), hydroxyapatite solution formed a gel around and within the pores of the poly(L-lactide-co-ε-caprolactone) scaffold at 37 ºC, within 1 min, that was stable for 3 weeks. The peptide functionalization was also successful where an aliphatic polyester of L-lactide was functionalized with different oligopeptides using a grafter (ethyl hept-6-enoylalaninate) and chemo-enzymatic synthesis.

The thermal properties of poly(L-lactide-co-hydroxybutyrate) were tailored (by modification of the microstructure) to potentially improve the processability of the aliphatic polyester.  The results showed that the yttrium salan catalyst was the most successful, yielding high molecular weight copolymers in shorter time. They also showed that the Tg could be tailored by varying the amount of rac-β-butyrolactone in the copolymer to better suit thermal processing techniques, such as 3D printing.

Place, publisher, year, edition, pages
Stockholm: KTH Royal Institute of Technology, 2018. 78 p.
Series
TRITA-CHE-Report, ISSN 1654-1081 ; 2017:35
Keyword
Polymer synthesis, enzymatic synthesis, degradable polyesters, peptides, scaffolds
National Category
Polymer Technologies
Research subject
Chemical Engineering
Identifiers
urn:nbn:se:kth:diva-219550 (URN)978-91-7729-615-7 (ISBN)
Public defence
2018-01-15, F3, Lindstedtsvägen 26, Stockholm, 09:00 (English)
Opponent
Supervisors
Funder
Swedish Research Council, 2013-3764
Note

QC 20171207

Available from: 2017-12-07 Created: 2017-12-07 Last updated: 2017-12-07Bibliographically approved

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Finne-Wistrand, Anna

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