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Solution NMR and racemic crystallography provide insights into a novel structural class of cyclic plant peptides
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- Payne, Colton D. (författare)
- Univ Queensland, Sch Biomed Sci, Brisbane, Qld 4072, Australia.
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- Vadlamani, Grishma (författare)
- Curtin Univ, Ctr Crop & Dis Management, Sch Mol & Life Sci, Bentley, WA 6102, Australia.;Univ Western Australia, Sch Mol Sci, Crawley, WA 6009, Australia.;Univ Western Australia, ARC Ctr Excellence Plant Energy Biol, Sch Mol Sci, Crawley, WA 6009, Australia.
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- Hajiaghaalipour, Fatemeh (författare)
- Univ Queensland, Sch Biomed Sci, Brisbane, Qld 4072, Australia.
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- Univ Queensland, Sch Biomed Sci, Brisbane, Qld 4072, Australia Curtin Univ, Ctr Crop & Dis Management, Sch Mol & Life Sci, Bentley, WA 6102, Australia.;Univ Western Australia, Sch Mol Sci, Crawley, WA 6009, Australia.;Univ Western Australia, ARC Ctr Excellence Plant Energy Biol, Sch Mol Sci, Crawley, WA 6009, Australia. (creator_code:org_t)
- 2021
- 2021
- Engelska.
- Ingår i: RSC CHEMICAL BIOLOGY. - : Royal Society of Chemistry. - 2633-0679. ; 2:6, s. 1682-1691
- Tidskriftsartikel (refereegranskat)
Abstract
Ämnesord
Stäng
- Head-to-tail cyclic and disulfide-rich peptides are natural products with applications in drug design. Among these are the PawS-Derived Peptides (PDPs) produced in seeds of the daisy plant family. PDP-23 is a unique member of this class in that it is twice the typical size and adopts two beta-hairpins separated by a hinge region. The beta-hairpins, both stabilised by a single disulfide bond, fold together into a V-shaped tertiary structure creating a hydrophobic core. In water two PDP-23 molecules merge their hydrophobic cores to form a square prism quaternary structure. Here, we synthesised PDP-23 and its enantiomer comprising d-amino acids and achiral glycine, which allowed us to confirm these solution NMR structural data by racemic crystallography. Furthermore, we discovered the related PDP-24. NMR analysis showed that PDP-24 does not form a dimeric structure and it has poor water solubility, but in less polar solvents adopts near identical secondary and tertiary structure to PDP-23. The natural role of these peptides in plants remains enigmatic, as we did not observe any antimicrobial or insecticidal activity. However, the plasticity of these larger PDPs and their ability to change structure under different conditions make them appealing peptide drug scaffolds.
Ämnesord
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
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