C-14-Labelling of the natural steroid estrogens 17 alpha-estradiol, 17 beta-estradiol, and estrone
文献类型： 外文期刊
作者： Lan, Xianjin 1 ; Wang, Ting 3 ; Ewald, Franziska 1 ; Chen, Zaixin 5 ; Cui, Kai 6 ; Schaeffer, Andreas 1 ; Wang, Lianho 1 ;
作者机构： 1.Nanjing Univ, Sch Environm, State Key Lab Pollut Control & Resource Reuse, Nanjing 210023, Jiangsu, Peoples R China
2.Jiangxi Acad Agr Sci, Inst Soil Fertilizer & Resources Environm, Nanchang 330200, Jiangxi, Peoples R China
3.Dept Ecol & Environm Henan Prov, 10 Xueli Rd, Zhengzhou 450046, Henan, Peoples R China
4.Rhein Westfal TH Aachen, Inst Environm Res, Worringerweg 1, D-52074 Aachen, Germany
5.Yabang Med Res Inst, 66 Changhong West Rd, Changzhou 213145, Peoples R China
6.Nanjing Univ, Jinling Coll, Sch Chem & Life Sci, Nanjing 210089, Jiangsu, Peoples R China
关键词： C-14-labelling; Estrogens; Estradiol isomers; Stereoselective synthesis
期刊名称：JOURNAL OF HAZARDOUS MATERIALS （ 影响因子：10.588； 五年影响因子：10.129 ）
ISSN： 0304-3894
年卷期： 2019 年 375 卷
页码：
收录情况： SCI
摘要： The worldwide environmental occurrence of natural steroid estrogens has drawn increasing concerns. However, the fate of the estrogens, especially the a-isomer of estradiol, in the environmental matrices is still obscure. Using C-14-radioactively labelled forms of these estrogens can facilitate and is sometimes a prerequisite for studying their transformation and residual distribution in the environment, but the availability of labelled compounds (owing to commercially high prices or unavailable) hampers such studies. Here we developed simple and stable methods to synthesize C-14-labelled estradiol isomers and estrone using relatively low-priced [carboxyl.C-14]-labelled sodium acetate as a precursor. The radiochemical syntheses started from an enol lactone, which was prepared from nandrolone by oxidation to open the A-ring followed by recyclization. Inversion of the 17 beta-hydroxyl group into its 17 alpha-form was achieved via the Walden inversion using the Mitsunobu reaction. [3-C-14]17 beta-estradiol, [3-C-14]-17 alpha-estradiol, and [3-C-14]-estrone were synthesized in five, six, and seven steps with an overall radiochemical yield of 17.4%, 16.2%, and 13.9%, respectively. The synthesized C-14-labelled compounds provide materials for studying the fate and behavior of estrogens in complex environmental matrixes and for further synthesis of their C-14-labelled sulfate and glucuronide conjugates.
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