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A chiral GC–MS method for analysis of secondary amino acids after heptaluorobutyl chloroformate & methylamine derivatization

The result's identifiers

  • Result code in IS VaVaI

    <a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60077344%3A_____%2F21%3A00539439" target="_blank" >RIV/60077344:_____/21:00539439 - isvavai.cz</a>

  • Result on the web

    <a href="https://link.springer.com/content/pdf/10.1007/s00726-021-02949-1.pdf" target="_blank" >https://link.springer.com/content/pdf/10.1007/s00726-021-02949-1.pdf</a>

  • DOI - Digital Object Identifier

    <a href="http://dx.doi.org/10.1007/s00726-021-02949-1" target="_blank" >10.1007/s00726-021-02949-1</a>

Alternative languages

  • Result language

    angličtina

  • Original language name

    A chiral GC–MS method for analysis of secondary amino acids after heptaluorobutyl chloroformate & methylamine derivatization

  • Original language description

    L-amino acids (L-AAs) play diferent important roles in the physiology of all living organisms. Their chiral counterparts, D-amino acids (D-AAs) are increasingly being recognized as essential molecules in many biological systems. Secondary amino acids with cyclic structures, such as prolines, exhibit conformational rigidity and thus unique properties in the structural and protein folding. Despite their widespread occurrence, much less attention was paid to their chiral analysis, particularly when the minor, typically D-enantiomer, is present in low amounts in a complex biological matrix. In this paper, a cost-efective, chiral GC–MS method is described for capillary Chirasil-L-Val separation of eight cyclic secondary amino acid enantiomers with four-, ive-, and six-membered rings, involving azetidine-2-carboxylic acid, pipecolic acid, nipecotic acid, proline, isomeric cis/trans 3-hydroxy, 4-hydroxyproline, and cis/trans-5-hydroxy-L-pipecolic acid in the excess of its enantiomeric antipode. The sample preparation involves in-situ derivatization with heptaluorobutyl chloroformate, simultaneous liquid–liquid micro-extraction into isooctane followed by amidation of the arising low-polar derivatives with methylamine, an evaporation step, re-dissolution, and inal GC–MS analysis. The developed method was used for analyses of human bioluids, biologically active peptides containing chiral proline constituents, and collagen.

  • Czech name

  • Czech description

Classification

  • Type

    J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database

  • CEP classification

  • OECD FORD branch

    10406 - Analytical chemistry

Result continuities

  • Project

    <a href="/en/project/GA17-22276S" target="_blank" >GA17-22276S: New methods for metabolomic analysis of hardly determined metabolites</a><br>

  • Continuities

    P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Others

  • Publication year

    2021

  • Confidentiality

    S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Data specific for result type

  • Name of the periodical

    Amino Acids

  • ISSN

    0939-4451

  • e-ISSN

    1438-2199

  • Volume of the periodical

    53

  • Issue of the periodical within the volume

    3

  • Country of publishing house

    AT - AUSTRIA

  • Number of pages

    12

  • Pages from-to

    347-358

  • UT code for WoS article

    000617850100002

  • EID of the result in the Scopus database

    2-s2.0-85101432503