Abstract

A simple and practical 10-step synthesis is reported for previously unknown diastereomers of C‑methylated spermine (Spm) analogue, 1,12-diamino-3,10-dimethyl-4,9-diazadodecane (3,10-Me₂Spm), starting from commercially available enantiomers of 2-(Boc-amino)-1-propanol. Title compounds were prepared in gram scale, in excellent overall yields and enantiomeric purity. Since biochemical properties of 3,10‑Me₂Spm can be regulated by changing the configuration of chiral center(s), these analogues are of obvious value for studying not only cellular functions of spermine, but even diseases associated with the disturbances of spermine metabolism.

中文翻译：

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3,10-二甲基亚精胺的（3 R，10 R）-和（3 S，10 S）-非对映异构体的合成

摘要

据报道，C-甲基化精胺（Spm）类似物1,12-二氨基-3,10-二甲基-4,9-二氮十二烷（3,10-Me ₂ Spm）的先前非对映异构体的合成简单而实用从2-（Boc-氨基）-1-丙醇的对映异构体开始。标题化合物以克级制备，具有优异的总收率和对映体纯度。由于可以通过改变手性中心的构型来调节3,10‑Me ₂ Spm的生化特性，因此这些类似物不仅对研究精胺的细胞功能，甚至对与精胺代谢紊乱有关的疾病都有研究价值。 。