| Post-translational amino acid isomerization: a functionally important D-amino acid in an excitatory peptide. | |
| | |
MedLine Citation:
|
PMID: 15561705 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
|
The post-translational modification of an L- to a D-amino acid has been documented in relatively few gene products, mostly in small peptides under 10 amino acids in length. In this report, we demonstrate that a 46-amino acid polypeptide toxin has one D-phenylalanine at position 44, and that the epimerization from an L-Phe to a D-Phe has a dramatic effect on the excitatory effects of the peptide. In one electrophysiological assay carried out, the D-Phe-containing peptide was extremely potent, whereas the unmodified polypeptide had no biological activity, demonstrating that the chirality of the post-translationally modified amino acid is functionally significant. The peptide toxin analyzed, r11a, belongs to the I-gene superfamily of conotoxins that has four disulfide cross-links. The D-Phe in r11a is at the third amino acid from the C terminus, the same relative position from the C-terminal end as the d-amino acid in omega-agatoxin TK from a spider, an unrelated peptide. Thus, although post-translational amino acid isomerization appears to have no strong specificity for the chemical nature of the amino acid side chain, the few peptides where this modification has been established suggest that there may be favored positions near the N or C terminus that are preferential sites for isomerization to a D-amino acid. |
| | |
Authors:
|
Olga Buczek; Doju Yoshikami; Grzegorz Bulaj; Elsie C Jimenez; Baldomero M Olivera |
Related Documents
:
|
17183515 - Effect of osteonectin-derived peptide on the viscoelasticity of hydrogel/apatite nanoco... 16231205 - Catalytically increased prebiotic peptide formation: ditryptophan, dilysine, and diserine. 4349115 - Complete amino acid analysis of peptides and proteins after hydrolysis by a mixture of ... 18265435 - Isolation and characterization of a c12-lipopeptide produced by bacillus subtilis hso 121. 12081315 - Binding affinities of commonly employed sensitizers of viral inactivation. 6122585 - Effects of amphetamine and amfonelic acid on the disposition of striatal newly synthesi... |
Publication Detail:
|
Type: Journal Article; Research Support, U.S. Gov't, P.H.S. Date: 2004-11-23 |
Journal Detail:
|
Title: The Journal of biological chemistry Volume: 280 ISSN: 0021-9258 ISO Abbreviation: J. Biol. Chem. Publication Date: 2005 Feb |
Date Detail:
|
Created Date: 2005-02-07 Completed Date: 2005-04-05 Revised Date: 2007-11-14 |
Medline Journal Info:
|
Nlm Unique ID: 2985121R Medline TA: J Biol Chem Country: United States |
Other Details:
|
Languages: eng Pagination: 4247-53 Citation Subset: IM |
Affiliation:
|
Department of Biology, University of Utah, Salt Lake City, Utah 84112, USA. |
Export Citation:
|
APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
|
Amino Acid Sequence Amino Acids / chemistry* Animals Biological Assay Chromatography, High Pressure Liquid Chymotrypsin / chemistry Conotoxins / chemistry Disulfides / chemistry Electrophysiology Endopeptidases / chemistry Mass Spectrometry Metalloendopeptidases Mice Molecular Sequence Data Muscles / metabolism Oxygen / chemistry Peptides / chemistry* Phenylalanine / chemistry Protein Conformation Protein Folding Protein Isoforms Protein Processing, Post-Translational* Protein Structure, Tertiary Rana pipiens Sequence Homology, Amino Acid Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization Time Factors |
| Grant Support | |
ID/Acronym/Agency:
|
GM 48677/GM/NIGMS NIH HHS |
| Chemical | |
Reg. No./Substance:
|
0/Amino Acids; 0/Conotoxins; 0/Disulfides; 0/Peptides; 0/Protein Isoforms; 63-91-2/Phenylalanine; 7782-44-7/Oxygen; EC 3.4.-/Endopeptidases; EC 3.4.21.1/Chymotrypsin; EC 3.4.24.-/Metalloendopeptidases; EC 3.4.24.33/endoproteinase Asp-N |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
Previous Document: Phosphorylation-independent beta-arrestin translocation and internalization of leukotriene B4 recept...
Next Document: DNA polymerase beta and flap endonuclease 1 enzymatic specificities sustain DNA synthesis for long p...