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

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 2017卷 / 47期

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

页码：7012 / 7018

页数：7

共 50 条

[31] Stereoselective Synthesis of 2-Deoxy-β-glycosides Using Anomeric O-Alkylation/Arylation
Morris, William J.
Shair, Matthew D.
ORGANIC LETTERS, 2009, 11 (01) : 9 - 12
[32] Ortho-(1-phenylvinyl)benzyl glycosides: Ether-type glycosyl donors for the efficient synthesis of both O-glycosides and nucleosides
Li, Penghua
He, Haiqing
Xu, Lili
Huang, Yingying
Chen, Zixi
Zhang, Yunqin
Yang, Rui
Xiao, Guozhi
GREEN SYNTHESIS AND CATALYSIS, 2020, 1 (02): : 160 - 166
[33] Stereoselective synthesis of 2-O-MEM-2,3-unsaturated-β-O-glycosides and elaboration to useful synthetic tools
Di Bussolo, Valeria
Fiasella, Annalisa
Frau, Ileana
Favero, Lucilla
Crotti, Paolo
TETRAHEDRON LETTERS, 2010, 51 (38) : 4937 - 4941
[34] Calcium Carbide: From Elemental Carbon to Isotope-Economic Synthesis of 13C2-Labeled Heterocycles
Ledovskaya, Maria S.
Voronin, Vladimir V.
Valov, Nikita R.
Samoylenko, Dmitriy E.
CHINESE JOURNAL OF CHEMISTRY, 2023, 41 (21) : 2810 - 2818
[35] Efficient one-pot synthesis of 2-hydroxyethyl per-O-acetyl glycosides
Tao, Hong-Wen
Wang, Xia
Yi, Ping-Gui
Deng, Zhi-Hong
Yu, Xian-Yong
Li, Xiao-Fang
CHEMICAL PAPERS, 2014, 68 (08) : 1132 - 1136
[36] 3,5-Dinitrobenzoic acid catalyzed synthesis of 2,3-unsaturated O- and S-glycosides and tetrahydropyranylation of alcohols and phenols
Bodipati, Naganjaneyulu
Palla, Srinivasa Rao
Komera, Venkateshwarlu
Peddinti, Rama Krishna
TETRAHEDRON LETTERS, 2014, 55 (50) : 6878 - 6881
[37] Stereoselective Synthesis of Quercetin 3-O-Glycosides of 2-Amino-2-Deoxy-d-Glucose Under Phase Transfer Catalytic Conditions
Cao, Zhiling
Qu, Yingying
Zhou, Jiexing
Liu, Weiwei
Yao, Guowei
JOURNAL OF CARBOHYDRATE CHEMISTRY, 2015, 34 (01) : 28 - 40
[38] Synthesis and Evaluation of Benzophenone O-Glycosides as a-Glucosidase Inhibitors
Liu, Qingchao
Guo, Tiantian
Li, Wenhong
Li, Dong
Feng, Zili
ARCHIV DER PHARMAZIE, 2012, 345 (10) : 771 - 783
[39] First Total Synthesis of the Bioactive Arylnaphthyl Lignan 4-O-Glycosides Phyllanthusmin D and 4"-O-Acetylmananthoside B
Liu, Lei
Hu, Yang
Liu, Hui
Liu, De-Yong
Xia, Jian-Hui
Sun, Jian-Song
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (25) : 3674 - 3680
[40] 34S: A New Opportunity for the Efficient Synthesis of Stable Isotope Labeled Compounds
Ren, Sumei
Fier, Patrick S.
Ren, Hong
Hoover, Andrew J.
Hesk, David
Marques, Rosemary
Mergelsberg, Ingrid
CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (28) : 7133 - 7136

← 1 2 3 4 5 →