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Isolation, characte...
Isolation, characterization, and synthesis of the Barrettides : disulfide-containing peptides from the marine sponge Geodia barretti
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- Carstens, Bodil B. (author)
- Uppsala universitet,Avdelningen för farmakognosi,Univ Queensland, Inst Mol Biosci, Brisbane, Qld 4072, Australia.,Ulf Goransson,University of Queensland, Australia
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- Rosengren, K. Johan (author)
- University of Queensland, Australia,Univ Queensland, Sch Biomed Sci, Brisbane, Qld 4072, Australia.
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- Gunasekera, Sunithi (author)
- Uppsala universitet,Avdelningen för farmakognosi,Ulf Goransson,Uppsala University, Sweden
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- Schempp, Stefanie (author)
- Uppsala universitet,Avdelningen för farmakognosi,Ulf Goransson,Uppsala University, Sweden
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- Bohlin, Lars (author)
- Uppsala universitet,Avdelningen för farmakognosi,Uppsala University, Sweden
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- Dahlström, Mia (author)
- RISE,Material och ytteknik,SP Tech Res Inst Sweden, Dept Chem Mat & Surfaces, SE-41346 Gothenburg, Sweden.
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- Clark, Richard J. (author)
- University of Queensland, Australia,Univ Queensland, Sch Biomed Sci, Brisbane, Qld 4072, Australia.
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- Göransson, Ulf (author)
- Uppsala universitet,Avdelningen för farmakognosi,Ulf Goransson,Uppsala University, Sweden
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(creator_code:org_t)
- 2015-07-29
- 2015
- English.
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In: Journal of Natural Products. - : American Chemical Society (ACS). - 0163-3864 .- 1520-6025. ; 78:8, s. 1886-1893
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Abstract
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- Two disulfide-containing peptides, barrettides A (1) and B (2), from the cold-water marine sponge Geodia barretti are described. Those 31 amino acid residue long peptides were sequenced using mass spectrometry methods and structurally characterized using NMR spectroscopy. The structure of 1 was confirmed by total synthesis using the solid-phase peptide synthesis approach that was developed. The two peptides were found to differ only at a single position in their sequence. The three-dimensional structure of 1 revealed that these peptides possess a unique fold consisting of a long β-hairpin structure that is cross-braced by two disulfide bonds in a ladder-like arrangement. The peptides are amphipathic in nature with the hydrophobic and charged residues clustered on separate faces of the molecule. The barrettides were found not to inhibit the growth of either Escherichia coli or Staphylococcus aureus but displayed antifouling activity against barnacle larvae (Balanus improvisus) without lethal effects in the concentrations tested. (Figure Presented).
Subject headings
- NATURVETENSKAP -- Biologi -- Biokemi och molekylärbiologi (hsv//swe)
- NATURAL SCIENCES -- Biological Sciences -- Biochemistry and Molecular Biology (hsv//eng)
- MEDICIN OCH HÄLSOVETENSKAP -- Medicinska och farmaceutiska grundvetenskaper -- Farmakologi och toxikologi (hsv//swe)
- MEDICAL AND HEALTH SCIENCES -- Basic Medicine -- Pharmacology and Toxicology (hsv//eng)
Publication and Content Type
- ref (subject category)
- art (subject category)
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