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
  • [31] SYNTHESIS OF STABLE ISOTOPE-LABELED ANALOGS OF THE CYSTEINE AND N-ACETYLCYSTEINE CONJUGATES OF TETRACHLOROETHYLENE
    BARTELS, MJ
    MINER, VW
    JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 1990, 28 (02): : 209 - 214
  • [32] Enzymatic synthesis of region-specific isotope-labeled DNA oligomers for NMR analysis
    Mer, G
    Chazin, WJ
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (03) : 607 - 608
  • [33] Stereoselective synthesis of triply isotope-labeled ser, cys, and ala: Amino acids for stereoarray isotope labeling technology
    Terauchi, Tsutomu
    Kobayashi, Kuniko
    Okuma, Kosuke
    Oba, Makoto
    Nishiyama, Kozaburo
    Kainosho, Masatsune
    ORGANIC LETTERS, 2008, 10 (13) : 2785 - 2787
  • [34] ISOTOPE-LABELED INSECTICIDES - PREPARATION OF LABELED 2-ETHYLTHIOETHANOL, A DEMETON INTERMEDIATE
    GROVES, K
    HAUGWITZ, R
    JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1961, 9 (04) : 262 - &
  • [35] SYNTHESIS OF HEXACHLOROCYCLOTRIPHOSPHAZATRIENE, LABELED WITH 15-N ISOTOPE
    PASHINA, YN
    STEPANOV, BI
    ZHURNAL OBSHCHEI KHIMII, 1974, 44 (02): : 455 - 455
  • [36] Synthesis, Purification, and Mass Spectrometric Characterization of Stable Isotope-Labeled Amadori-Glycated Phospholipids
    He, Xiaobo
    Zhang, Qibin
    ACS OMEGA, 2018, 3 (11): : 15725 - 15733
  • [37] Facile synthesis of stable isotope-labeled antibacterial agent RWJ-416457 and its metabolite
    Lin, Ronghui
    Weaner, Larry E.
    JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2012, 55 (08): : 296 - 299
  • [38] AN EFFICIENT CHEMOMICROBIOLOGICAL SYNTHESIS OF STABLE ISOTOPE-LABELED L-TYROSINE AND L-PHENYLALANINE
    WALKER, TE
    MATHENY, C
    STORM, CB
    HAYDEN, H
    JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (08): : 1175 - 1179
  • [39] Cell-free synthesis of stable isotope-labeled internal standards for targeted quantitative proteomics
    Narumi, Ryohei
    Masuda, Keiko
    Tomonaga, Takeshi
    Adachi, Jun
    Ueda, Hiroki R.
    Shimizu, Yoshihiro
    SYNTHETIC AND SYSTEMS BIOTECHNOLOGY, 2018, 3 (02) : 97 - 104
  • [40] Prussian blue nanoparticles as isotope-labeled and fluorescent contrast material
    Forgach, Laszlo
    Kiss-Hegedus, Nikolett
    Varga, Zoltan
    Kovacs, Noemi
    Horvath, Ildiko
    Mathe, Domokos
    Szigeti, Krisztian
    BIOPHYSICAL JOURNAL, 2023, 122 (03) : 551A - 551A