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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.
MedLine Citation:
PMID:  23565145     Owner:  NLM     Status:  In-Data-Review    
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.
Mariana T Q de Magalhães; Eder A Barbosa; Maura V Prates; Rodrigo M Verly; Victor Hugo O Munhoz; Ivan E de Araújo; Carlos Bloch
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Publication Detail:
Type:  Journal Article     Date:  2013-04-02
Journal Detail:
Title:  PloS one     Volume:  8     ISSN:  1932-6203     ISO Abbreviation:  PLoS ONE     Publication Date:  2013  
Date Detail:
Created Date:  2013-04-08     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  101285081     Medline TA:  PLoS One     Country:  United States    
Other Details:
Languages:  eng     Pagination:  e59255     Citation Subset:  IM    
Laboratório de Espectrometria de Massa, Embrapa Recursos Genéticos e Biotecnologia, Brasília-Distrito Federal, Brasil ; Departamento de Biologia Celular, Pós-Graduação em Biologia Molecular, Universidade de Brasília, Brasília, Distrito Federal, Brasil ; The John B. Pierce Laboratory, New Haven, Connecticut, United States of America.
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