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Microwave-assisted total synthesis of macrocyclic cystine knot miniproteins
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Division of Pharmacognosy.
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Division of Pharmacognosy.
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Division of Pharmacognosy.
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Division of Pharmacognosy.
2010 (English)In: Journal of Peptide Science, ISSN 1075-2617, E-ISSN 1099-1387, Vol. 16, no S1, 79-79 p.Article in journal, Meeting abstract (Other academic) Published
Abstract [en]

Microwave-assisted total synthesis of macrocyclic cystine knot miniproteins

SK Park, S Gunasekera, T Aboye, U Göransson Division of pharmacognosy, Uppsala university, UPPSALA, Sweden Cyclotides are mini-proteins of approximately 30 amino acids residues that have a unique structure consisting of a head-to-tail cyclic backbone with a knotted arrangement of three disulfide bonds [1]. This unique structure provides exceptional stability to chemical, enzymatic and thermal treatments [2,3]. Cyclotides display various bioactivities, such as anti-HIV, uterotonic, cytotoxic, and insecticidal activity [4]. Due to the unique structural stability, cyclotides have been implicated as ideal drug scaffolds and for development into agricultural and biotechnological agents [2]. In the current work, we represent the first method for total synthesis of cyclotides based on Fmoc-SPPS assisted by microwave. This protocol adopts a strategy that combines the optimized microwave assisted chemical reactions for Fmoc-SPPS of peptide backbone synthesis, thioesterification of the C-terminal carboxylic acid of the peptide and a one pot reaction that promotes cyclisation through native chemical ligation and oxidative folding. The application of this protocol was exemplified for the synthesis of two prototypic cyclotides; kalata B1 and MCOTI-II

Place, publisher, year, edition, pages
2010. Vol. 16, no S1, 79-79 p.
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Pharmaceutical Sciences
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URN: urn:nbn:se:uu:diva-142474DOI: 10.1002/psc.1303OAI: oai:DiVA.org:uu-142474DiVA: diva2:387444
Note
Meeting Abstract, abstract number:503Available from: 2011-01-14 Created: 2011-01-14 Last updated: 2017-12-11Bibliographically approved

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