Gerhardt, Heike and Sievers-Engler, Adrian and Jahanshah, Ghazaleh and Pataj, Zoltan and Ianni, Federica and Gross, Harald and Lindner, Wolfgang and Laemmerhofer, Michael (2016) Methods for the comprehensive structural elucidation of constitution and stereochemistry of lipopeptides. JOURNAL OF CHROMATOGRAPHY A, 1428. pp. 280-291. ISSN 0021-9673, 1873-3778
Full text not available from this repository. (Request a copy)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 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.
| Item Type: | Article |
|---|---|
| Uncontrolled 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 |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Medicine > Lehrstuhl für Klinische Chemie und Laboratoriumsmedizin |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 18 Mar 2019 14:27 |
| Last Modified: | 18 Mar 2019 14:27 |
| URI: | https://pred.uni-regensburg.de/id/eprint/2549 |
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