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Aboye, Teshome Leta
Publications (3 of 3) Show all publications
Park, S., Gunasekera, S., Aboye, T. L. & Göransson, U. (2010). An Efficient Approach for the Total Synthesis of Cyclotides by Microwave Assisted Fmoc-SPPS. International Journal of Peptide Research and Therapeutics, 16(3), 167-176
Open this publication in new window or tab >>An Efficient Approach for the Total Synthesis of Cyclotides by Microwave Assisted Fmoc-SPPS
2010 (English)In: International Journal of Peptide Research and Therapeutics, ISSN 1573-3149, Vol. 16, no 3, p. 167-176Article in journal (Refereed) Published
Abstract [en]

Cyclotides are mini-proteins of approximately 30 amino acid residues that have a unique structure consisting of a head-to-tail cyclized backbone and a knotted arrangement of three disulfide bonds. This unique cyclotide structure provides exceptional stability to chemical, enzymatic and thermal treatments and has been implicated as an ideal drug scaffold for the development into agricultural and biotechnological agents. In the current work, we present the first method for microwave assisted Fmoc-SPPS of cyclotides. This protocol adopts a strategy that combines optimized microwave assisted chemical reactions for Fmoc-SPPS of the peptide backbone, the cleavage of the protected peptide and the introduction of a thioester at the C-terminal carboxylic acid to obtain the head-to-tail cyclized cyclotide backbone by native chemical ligation. To exemplify the utility of this protocol in the synthesis of a wide array of different cyclotide sequences we synthesized representative members from the three cyclotide subfamilies-the Mobius kalata B1, the bracelet cycloviolacin O2 and the trypsin inhibitory MCoTI-II. In addition, a "one pot" reaction promoting both cyclization and oxidative folding of crude peptide thioester was adapted for kalata B1 and MCoTI-II.

Keywords
Cyclotides, Microwave chemistry, Fmoc-SPPS, Circular proteins, Cystine knot, Native chemical ligation
National Category
Pharmaceutical Sciences
Identifiers
urn:nbn:se:uu:diva-134899 (URN)10.1007/s10989-010-9221-0 (DOI)000281682600007 ()
Available from: 2010-12-02 Created: 2010-12-02 Last updated: 2018-01-12Bibliographically approved
Aboye, T. L., Burman, R. & Göransson, U. Design, synthesis, structural and biological evaluation of backbone-engineered cyclotides.
Open this publication in new window or tab >>Design, synthesis, structural and biological evaluation of backbone-engineered cyclotides
(English)Manuscript (preprint) (Other academic)
Identifiers
urn:nbn:se:uu:diva-145719 (URN)
Available from: 2011-02-10 Created: 2011-02-10 Last updated: 2011-05-04
Aboye, T. L., Rosengren, J., Gunasekera, S., Bruhn, G. J., El-Seedi, H. & Göransson, U. Discovery, synthesis, and structural determination of a toxine-like disulfide-rich peptide from the cactus Trichoserus pachanoi.
Open this publication in new window or tab >>Discovery, synthesis, and structural determination of a toxine-like disulfide-rich peptide from the cactus Trichoserus pachanoi
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(English)Manuscript (preprint) (Other academic)
Identifiers
urn:nbn:se:uu:diva-145716 (URN)
Available from: 2011-02-10 Created: 2011-02-10 Last updated: 2011-05-04
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