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| Content Provider | World Health Organization (WHO)-Global Index Medicus |
|---|---|
| Author | Pataj, Zoltán Ianni, Federica Gross, Harald Lindner, Wolfgang Jahanshah, Ghazaleh Sievers-Engler, Adrian Lämmerhofer, Michael Gerhardt, Heike |
| Description | Country affiliation: Germany Author Affiliation: Gerhardt H ( Institute of Pharmaceutical Sciences, University of Tübingen, Auf der Morgenstelle 8, 72076 Tübingen, Germany.); Sievers-Engler A ( Institute of Pharmaceutical Sciences, University of Tübingen, Auf der Morgenstelle 8, 72076 Tübingen, Germany.); Jahanshah G ( Institute of Pharmaceutical Sciences, University of Tübingen, Auf der Morgenstelle 8, 72076 Tübingen, Germany.); Pataj Z ( Institute of Pharmaceutical Sciences, University of Tübingen, Auf der Morgenstelle 8, 72076 Tübingen, Germany); Ianni F ( Institute of Pharmaceutical Sciences, University of Tübingen, Auf der Morgenstelle 8, 72076 Tübingen, Germany); Gross H ( Institute of Pharmaceutical Sciences, University of Tübingen, Auf der Morgenstelle 8, 72076 Tübingen, Germany.); Lindner W ( Department of Analytical Chemistry, University of Vienna, Waehringer Strasse 38, 1090 Vienna, Austria.); Lämmerhofer M ( Institute of Pharmaceutical Sciences, University of Tübingen, Auf der Morgenstelle 8, 72076 Tübingen, Germany. Electronic address: michael.laemmerhofer@uni-tuebingen.de.) |
| Abstract | A panel of methods of general suitability for complete structural elucidation of the stereochemistry of cyclopeptides, depsipeptides and lipopeptides is presented and described in detail. The suitability of the proposed methods was exemplified on the lipopeptide poaeamide from Pseudomonas poae. Amino acid configurations have been assigned by direct LC enantiomer separation with Chiralpak ZWIX(+) and were confirmed by GC enantiomer separation on Chirasil L-Val. 3-Hydroxydecanoic acid absolute configuration was analyzed on Chiralpak ZWIX(+) and confirmed by injection on ZWIX(-) which showed opposite elution order. Plenty of d-amino acids have been found in this lipopeptide. It contained in total 5 Leu residues of which one had d-configuration. The position of the d-Leu in the peptide sequence was determined by pepsin and chemical digestions in combination with isolation of diagnostic peptide-fragments and subsequent identification of absolute configurations of the Leu residues. This allowed pinpointing the position of the d-amino acid. The complementarity of the peptide retention profiles on Chiralpak ZWIX column as compared to both RPLC and HILIC suggests its great utility as an alternative peptide separation tool. |
| ISSN | 00219673 |
| Volume Number | 1428 |
| e-ISSN | 18733778 |
| Journal | Journal of Chromatography A |
| Language | English |
| Publisher | Elsevier |
| Publisher Date | 2016-01-08 |
| Publisher Place | Netherlands |
| Access Restriction | One Nation One Subscription (ONOS) |
| Subject Keyword | Chemistry Techniques, Analytical Methods Lipopeptides Chemistry Amino Acids Hydrolysis Pepsin A Metabolism Peptides, Cyclic Protein Conformation Stereoisomerism Journal Article Research Support, Non-u.s. Gov't Discipline Analytical Chemistry |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Medicine Analytical Chemistry Biochemistry |
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