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| Content Provider | World Health Organization (WHO)-Global Index Medicus |
|---|---|
| Author | Todorovski, Toni Fedorova, Maria Hennig, Lothar Hoffmann, Ralf |
| Description | Country affiliation: Germany Author Affiliation: Todorovski T ( Institute of Bioanalytical Chemistry, Center for Biotechnology and Biomedicine (BBZ), Faculty of Chemistry and Mineralogy, Universität Leipzig, Leipzig, Germany.) |
| Abstract | ROS, continuously produced in cells, can reversibly or irreversibly oxidize proteins, lipids, and DNA. At the protein level, cysteine, methionine, tryptophan, and tyrosine residues are particularly prone to oxidation. Here, we describe the solid phase synthesis of peptides containing four different oxidation products of tryptophan residues that can be formed by oxidation in proteins in vitro and in vivo: 5-HTP, Oia, Kyn, and NFK. First, we synthesized Oia and NFK by selective oxidation of tryptophan and then protected the -amino group of both amino acids, and the commercially available 5-HTP, with Fmoc-succinimide. High yields of Fmoc-Kyn were obtained by acid hydrolysis of Fmoc-NFK. All four Fmoc derivatives were successfully incorporated, at high yields, into three different peptide sequences from skeletal muscle actin, creatin kinase (M-type), and ß-enolase. The correct structure of all modified peptides was confirmed by tandem mass spectrometry. Interestingly, isobaric peptides containing 5-HTP and Oia were always well separated in an acetonitrile gradient with TFA as the ion-pair reagent on a C18-phase. Such synthetic peptides should prove useful in future studies to distinguish isobaric oxidation products of tryptophan. |
| File Format | HTM / HTML |
| ISSN | 10752617 |
| Issue Number | 4 |
| Volume Number | 17 |
| e-ISSN | 10991387 |
| Journal | Journal of Peptide Science |
| Language | English |
| Publisher | Wiley |
| Publisher Date | 2011-04-01 |
| Publisher Place | Great Britain (UK) |
| Access Restriction | One Nation One Subscription (ONOS) |
| Subject Keyword | Discipline Biochemistry 5-hydroxytryptophan Chemistry Alanine Analogs & Derivatives Kynurenine Peptides Chemical Synthesis Amino Acid Sequence Humans Molecular Sequence Data Molecular Structure Oxidation-reduction Tryptophan Journal Article |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Structural Biology Medicine Drug Discovery Biochemistry Molecular Biology Pharmacology Molecular Medicine |
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