甘遂烷酰胺 C 的合成与结构修正。
Synthesis and Structural Revision of Glyphaeaside C.
机构信息
School of Chemistry and Molecular Bioscience, University of Wollongong, Wollongong, New South Wales 2522, Australia.
Department of Hospital Pharmacy, University of Toyama, Sugitani, Toyama 2630, Japan.
出版信息
Org Lett. 2021 May 21;23(10):4029-4033. doi: 10.1021/acs.orglett.1c01248. Epub 2021 Apr 30.
The iminosugar core of natural glyphaeaside C, originally assigned as a derivative of the piperidine natural product 1-deoxynojirimycin (DNJ), has been revised as a derivative of 2,5-dideoxy-2,5-imino-l-mannitol (l-DMDP) by the total synthesis of its enantiomer. This revised l-DMDP-derived configuration is the first of its kind to be observed in nature. The prepared iminosugars displayed the nanomolar inhibition of bovine liver β-glucosidase and β-galactosidase.
天然 Glyphaeaside C 的亚氨基糖核心，最初被指定为哌啶天然产物 1-去氧野尻霉素（DNJ）的衍生物，通过其对映异构体的全合成被修订为 2,5-二脱氧-2,5-亚氨基-D-甘露醇（l-DMDP）的衍生物。这种经修正的 l-DMDP 衍生构型是自然界中首次观察到的。所制备的亚氨基糖显示出对牛肝β-葡萄糖苷酶和β-半乳糖苷酶的纳米摩尔抑制作用。
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