Iminosugar

[1] The first iminosugar to be isolated from a natural source, 1-deoxynojirimycin (DNJ), found in Mulberry, was reported in 1976, but few others were discovered until many years later.

DNJ was modified to produce two derivatives now used as medicines, N-hydroxyethyl-DNJ (miglitol) for diabetes and N-butyl-DNJ (miglustat) for Gaucher's disease.

Although the early compounds had biological activities due to glycosidase inhibition, an increasing number are being shown to have therapeutic potential without being glycosidase inhibitors and may interact with sugar receptors in the body or chaperone deficient enzymes such as in lysosomal storage disorders or in cystic fibrosis.

[2] The nitrogen of the iminosugar ring structure is a hemiaminal linkage, which, like the hemiacetal of a regular glycoside, is unstable.

The 1-deoxy analogs of iminosugars are C-glycosides, with the nitrogen as part of an ordinary amine linkage.