Gerhardt, Heike ; Sievers-Engler, Adrian ; Jahanshah, Ghazaleh ; Pataj, Zoltán ; Ianni, Federica ; Gross, Harald ; Lindner, Wolfgang ; Lämmerhofer, Michael
Alternative Links zum Volltext:DOIVerlag
| Dokumentenart: | Artikel |
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| Titel eines Journals oder einer Zeitschrift: | Journal of Chromatography A |
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| Verlag: | ELSEVIER SCIENCE BV |
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| Ort der Veröffentlichung: | AMSTERDAM |
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| Band: | 1428 |
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| Seitenbereich: | S. 280-291 |
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| Datum: | 2016 |
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| Institutionen: | Medizin > Lehrstuhl für Klinische Chemie und Laboratoriumsmedizin |
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| Identifikationsnummer: | | Wert | Typ |
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| 10.1016/j.chroma.2015.05.065 | DOI |
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| Stichwörter / Keywords: | CHIRAL STATIONARY PHASES; PERFORMANCE LIQUID-CHROMATOGRAPHY; AMINO-ACID ENANTIOMERS; HPLC-MS METHOD; MASS-SPECTROMETRY; MARFEYS REAGENT; ION-EXCHANGERS; SEPARATION; CINCHONA; ENANTIOSEPARATION; Depsipeptide; Cyclic lipopeptide; Absolute configuration; Chiral separation; Enantioselective chromatography; HPLC; GC; Chiralpak ZWIX; Chirasil L-Val; Amino acids; 3-Hydroxyalkanoic acids |
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| Dewey-Dezimal-Klassifikation: | 500 Naturwissenschaften und Mathematik > 540 Chemie |
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| Status: | Veröffentlicht |
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| Begutachtet: | Ja, diese Version wurde begutachtet |
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| An der Universität Regensburg entstanden: | Ja |
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| Dokumenten-ID: | 41990 |
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Web of Science
Zusammenfassung
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(+) ...
Zusammenfassung
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 n-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. (C) 2015 Elsevier B.V. All rights reserved.
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