ArticlePloS one2013
Conformational and functional effects induced by D- and L-amino acid epimerization on a single gene encoded peptide from the skin secretion of Hypsiboas punctatus.
Article in PloS one, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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10 citing papers in PubMed.
- Enhanced ion mobility resolution of Abeta isomers from human brain using high-resolution demultiplexing software.Analytical and bioanalytical chemistry · 2022Article
- Leveraging orthogonal mass spectrometry based strategies for comprehensive sequencing and characterization of ribosomal antimicrobial peptide natural products.Natural product reports · 2021Review
- Quantification of N-terminal amyloid-β isoforms reveals isomers are the most abundant form of the amyloid-β peptide in sporadic Alzheimer's disease.Brain communications · 2021Article
- Advancing d-amino acid-containing peptide discovery in the metazoan.Biochimica et biophysica acta. Proteins and proteomics · 2021Review
- A New Family of Diverse Skin Peptides from the Microhylid Frog GenusMolecules (Basel, Switzerland) · 2020Article
- Cleavage of Peptides from Amphibian Skin Revealed by Combining Analysis of Gland Secretion and in Situ MALDI Imaging Mass Spectrometry.ACS omega · 2018Article
- Linear and Differential Ion Mobility Separations of Middle-Down Proteoforms.Analytical chemistry · 2018Article
- Distinguishing d- and l-aspartic and isoaspartic acids in amyloid β peptides with ultrahigh resolution ion mobility spectrometry.Chemical communications (Cambridge, England) · 2017Article
- Structure and membrane interactions of the homodimeric antibiotic peptide homotarsinin.Scientific reports · 2017Article
- Site-specific characterization of (D)-amino acid containing peptide epimers by ion mobility spectrometry.Analytical chemistry · 2014Article
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7 authors.
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Abstract
Skin secretion of Hypsiboas punctatus is the source of a complex mixture of bioactive compounds where peptides and small proteins prevail, similarly to many other amphibians. Among dozens of molecules isolated from H. punctatus in a proteomic based approach, we report here the structural and functional studies of a novel peptide named Phenylseptin (FFFDTLKNLAGKVIGALT-NH2) that was purified as two naturally occurring D- and L-Phes configurations. The amino acid epimerization and C-terminal amidation for both molecules were confirmed by a combination of techniques including reverse-phase UFLC, ion mobility mass spectrometry, high resolution MS/MS experiments, Edman degradation, cDNA sequencing and solid-phase peptide synthesis. RMSD analysis of the twenty lowest-energy (1)H NMR structures of each peptide revealed a major 90° difference between the two backbones at the first four N-terminal residues and substantial orientation changes of their respective side chains. These structural divergences were considered to be the primary cause of the in vitro quantitative differences in antimicrobial activities between the two molecules. Finally, both molecules elicited equally aversive reactions in mice when delivered orally, an effect that depended entirely on peripheral gustatory pathways.
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