Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK.
J Org Chem. 2012 Sep 21;77(18):7777-92. doi: 10.1021/jo301243s. Epub 2012 Sep 6.
The enantiomers of glucuronolactone are excellent chirons for the synthesis of the 10 stereoisomeric 2,5-dideoxy-2,5-iminohexitols by formation of the pyrrolidine ring by nitrogen substitution at C2 and C5, with either retention or inversion of configuration; the stereochemistry at C3 may be adjusted during the synthesis to give seven stereoisomers from each enantiomer. A definitive side-by-side comparison of the glycosidase inhibition of a panel of 13 glycosidases showed that 8 of the 10 stereoisomers showed significant inhibition of at least one glycosidase.
葡萄糖醛内脂的对映异构体是合成 10 个立体异构的 2,5-二脱氧-2,5-亚氨基己糖醇的优秀手性中心，通过在 C2 和 C5 位的氮取代形成吡咯烷环，保留或反转构型；在合成过程中可以调整 C3 的立体化学，从每个对映异构体中得到七个立体异构体。对 13 种糖苷酶的糖苷酶抑制作用进行了明确的并排比较，结果表明 10 个立体异构体中的 8 个对至少一种糖苷酶具有显著的抑制作用。
