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Synthesis, Structural Characterization, and Bioactivity of the Stable Peptide RCB-1 from Ricinus communis
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Division of Pharmacognosy. Natl Univ Mongolia, Sch Engn & Appl Sci, Ulaanbaatar 46, Mongol Peo Rep..
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. Univ Malaya, Fac Sci, Dept Chem, Kuala Lumpur 50603, Malaysia..
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Division of Pharmacognosy.
2015 (English)In: Journal of natural products (Print), ISSN 0163-3864, E-ISSN 1520-6025, Vol. 78, no 11, 2545-2551 p.Article in journal (Refereed) Published
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Abstract [en]

The Ricinus communis biomarker peptides RCB-1 to -3 comprise homologous sequences of 19 (RCB-1) or 18 (RCB-2 and -3) amino acid residues. They all include four cysteine moieties, which form two disulfide bonds. However, neither the 3D structure nor the biological activity of any of these peptides is known. The synthesis of RCB-1, using microwave-assisted, Fmoc-based solid-phase peptide synthesis, and a method for its oxidative folding are reported. The tertiary structure of RCB-1, subsequently established using solution-state NMR, reveals a twisted loop fold with antiparallel ?-sheets reinforced by the two disulfide bonds. Moreover, RCB-1 was tested for antibacterial, antifungal, and cytotoxic activity, as well as in a serum stability assay, in which it proved to be remarkably stable.

Place, publisher, year, edition, pages
2015. Vol. 78, no 11, 2545-2551 p.
National Category
Medicinal Chemistry
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URN: urn:nbn:se:uu:diva-272306DOI: 10.1021/acs.jnatprod.5b00463ISI: 000366005800005PubMedID: 26509914OAI: oai:DiVA.org:uu-272306DiVA: diva2:894161
Funder
Swedish Research Council, 621-2007-567Swedish Foundation for Strategic Research , F06-0058
Available from: 2016-01-14 Created: 2016-01-13 Last updated: 2017-11-30Bibliographically approved

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Gunasekera, SunithiGöransson, Ulf

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