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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
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
URN: urn:nbn:se:kth:diva-144372DOI: 10.1021/bm4015254ISI: 000332756600005ScopusID: 2-s2.0-84896752024OAI: diva2:713283

QC 20140422

Available from: 2014-04-22 Created: 2014-04-22 Last updated: 2014-04-22Bibliographically approved

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Fagerland, JennyFinne-Wistrand, Anna
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