Enzymatic Fluoromethylation Enabled by the S-Adenosylmethionine Analog Te-Adenosyl-L-(fluoromethyl)homotellurocysteine,ACS Central Science

当前位置： X-MOL 学术 › ACS Cent. Sci. › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Enzymatic Fluoromethylation Enabled by the S-Adenosylmethionine Analog Te-Adenosyl-L-(fluoromethyl)homotellurocysteine
ACS Central Science ( IF 12.7 ) Pub Date : 2023-05-08 , DOI: 10.1021/acscentsci.2c01385
Syam Sundar Neti ₁ , Bo Wang ₁ , David F Iwig ₁ , Elizabeth L Onderko ₁ , Squire J Booker ₁

Affiliation

Fluoromethyl, difluoromethyl, and trifluoromethyl groups are present in numerous pharmaceuticals and agrochemicals, where they play critical roles in the efficacy and metabolic stability of these molecules. Strategies for late-stage incorporation of fluorine-containing atoms in molecules have become an important area of organic and medicinal chemistry as well as synthetic biology. Herein, we describe the synthesis and use of Te-adenosyl-L-(fluoromethyl)homotellurocysteine (FMeTeSAM), a novel and biologically relevant fluoromethylating agent. FMeTeSAM is structurally and chemically related to the universal cellular methyl donor S-adenosyl-L-methionine (SAM) and supports the robust transfer of fluoromethyl groups to oxygen, nitrogen, sulfur, and some carbon nucleophiles. FMeTeSAM is also used to fluoromethylate precursors to oxaline and daunorubicin, two complex natural products that exhibit antitumor properties.

中文翻译：

S-腺苷甲硫氨酸类似物 Te-腺苷-L-(氟甲基)高特鲁半胱氨酸实现酶促氟甲基化

氟甲基、二氟甲基和三氟甲基存在于许多药物和农用化学品中，它们在这些分子的功效和代谢稳定性中发挥着关键作用。在分子中后期掺入含氟原子的策略已成为有机化学和药物化学以及合成生物学的重要领域。在此，我们描述了Te-腺苷-L- (氟甲基)高特鲁半胱氨酸(FMeTeSAM)的合成和用途，这是一种新型且具有生物相关性的氟甲基化剂。 FMeTeSAM 在结构和化学上与通用细胞甲基供体S-腺苷-L-甲硫氨酸 (SAM) 相关，并支持氟甲基向氧、氮、硫和一些碳亲核试剂的稳健转移。 FMeTeSAM 还用于氟甲基化恶啉和柔红霉素前体，这两种复杂的天然产物具有抗肿瘤特性。

更新日期：2023-05-08

点击分享查看原文

点击收藏

公开下载

阅读更多本刊新发论文本刊介绍/投稿指南