Synthesis of Isotope-Labeled Deoxynivalenol-15-O-Glycosides

被引:2
|
作者
Weber, Julia [1 ]
Fruhmann, Philipp [1 ,2 ]
Hametner, Christian [1 ]
Schiessl, Alois [3 ]
Haeubl, Georg [3 ]
Froehlich, Johannes [1 ]
Mikula, Hannes [1 ]
机构
[1] Vienna Univ Technol TU Wien, Inst Appl Synthet Chem, Getreidemarkt 9, A-1060 Vienna, Austria
[2] CEST, Viktor Kaplan Str 2, A-2700 Wiener Neustadt, Austria
[3] Romer Labs, Technopk 1, A-3430 Tulln Donau, Austria
关键词
Glycosylation; Glycosides; Orthoesters; Natural products; Isotopic labeling; ACETYLATED DERIVATIVES; CHEMICAL-SYNTHESIS; MASKED MYCOTOXINS; O-GLYCOSYLATION; DEOXYNIVALENOL; ACID; GLUCOSIDE; ANALOGS; WHEAT;
D O I
10.1002/ejoc.201700934
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A versatile and efficient protocol for the Schmidt glycosylation of 3-acetyldeoxynivalenol (3-ADON) and subsequent deprotection has been developed to gain access to deoxynivalenol-15-O-glycosides in reasonable amounts for biological analysis and further investigations. By using this protocol with [C-13(6)]glycosyl donors, we were able to prepare isotope-labeled deoxynivalenol-15-O-glycosides, which are pivotal to enabling accurate quantification of masked mycotoxins by LC-MS.
引用
收藏
页码:7012 / 7018
页数:7
相关论文
共 50 条
  • [21] ISOTOPE-LABELED RNAS FROM HIV-1
    KING, GC
    XI, ZJ
    CHANG, DK
    MICHNICKA, MJ
    KHABASHESKU, O
    HARPER, JW
    JOURNAL OF CELLULAR BIOCHEMISTRY, 1993, : 242 - 242
  • [22] Spectrally accurate quantitative analysis of isotope-labeled compounds
    Kuehl, Don
    Wang, Yongdong
    Wang, Peter L.
    Zhou, Dawei
    RAPID COMMUNICATIONS IN MASS SPECTROMETRY, 2021,
  • [23] Four Isotope-Labeled Recombination Pathways of Ozone Formation
    Babikov, Dmitri
    Grushnikova, Elizaveta
    Gayday, Igor
    Teplukhin, Alexander
    MOLECULES, 2021, 26 (05):
  • [24] The synthesis of a tritium, carbon-14, and stable isotope-labeled cathepsin C inhibitors
    Allen, Paul
    Bragg, Ryan A.
    Caffrey, Moya
    Ericsson, Cecilia
    Hickey, Michael J.
    Kingston, Lee P.
    Elmore, Charles S.
    JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2017, 60 (02): : 124 - 129
  • [25] SYNTHESIS AND NMR-SPECTROSCOPY OF STABLE ISOTOPE-LABELED PHENOLS AND L-TYROSINES
    WINKEL, C
    AARTS, MWMM
    VANDERHEIDE, FR
    BUITENHUIS, EG
    LUGTENBURG, J
    RECUEIL DES TRAVAUX CHIMIQUES DES PAYS-BAS-JOURNAL OF THE ROYAL NETHERLANDS CHEMICAL SOCIETY, 1989, 108 (04): : 139 - 146
  • [26] Stable isotope-labeled peptides in study of protein aggregation
    Baldwin, MA
    AMYLOID, PRIONS, AND OTHER PROTEIN AGGREGATES, 1999, 309 : 576 - 591
  • [27] Production of isotope-labeled proteins in insect cells for NMR
    Bastian Franke
    Christian Opitz
    Shin Isogai
    Anne Grahl
    Leonildo Delgado
    Alvar D. Gossert
    Stephan Grzesiek
    Journal of Biomolecular NMR, 2018, 71 : 173 - 184
  • [28] Reconstitution of Nucleosomes with Differentially Isotope-labeled Sister Histones
    Liokatis, Stamatios
    JOVE-JOURNAL OF VISUALIZED EXPERIMENTS, 2017, (121):
  • [29] Production of isotope-labeled proteins in insect cells for NMR
    Franke, Bastian
    Opitz, Christian
    Isogai, Shin
    Grahl, Anne
    Delgado, Leonildo
    Gossert, Alvar D.
    Grzesiek, Stephan
    JOURNAL OF BIOMOLECULAR NMR, 2018, 71 (03) : 173 - 184
  • [30] Synthesis of stable isotope-labeled epothilone D using a degradation-reconstruction approach
    Burrell, Richard C.
    Turley, Wesley A.
    Bonacorsi, Samuel J., Jr.
    JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2015, 58 (09): : 361 - 369