Biosynthesis
1-Deoxynojirimycin is a polyhydroxylated piperidine alkaloid produced from D-Glucose in various plants, such as ''Commelina communis'', and in the ''Streptomyces'' and ''Bacillus'' bacteria. High quantities of this azasugar are produced in ''Bacillus subtilis'', a process initiated by a TYB gene cluster composed of gabT1 (aminotransferase), yktc1 (phosphatase), and gutB1 (oxidoreductase). In ''Bacillus subtilis,'' D-glucose first undergoes glycolysis, opening the 6 member ring and producing fructose-6-phosphate. GabT1 catalyzes transamination at the C2 position, followed by a dephosphorylation by the Yktc1 enzyme, resulting in 2-amino-2-deoxy-D-mannitol (ADM), an essential precursor. Regio-selective oxidation by GutB1 occurs at the exposed C6 hydroxyl of ADM, pushing a C2-N-C6 cyclization of the resulting 6-oxo intermediate, creating Manojirimycin (MJ). Epimerization of MJ at the C2 position yields the nojirimycin isomer. Nojirimycin is then dehydrated (loss of -OH at C1 position), along with reduction of the imine moiety. This results in the product 1-DNJ.Pathway variations
In the ''Streptomyces subrutilus'' species, a secondary pathway branching from the manojirimycin precursor results in 1-deoxymanojirimycin via dehydration and reduction of the isomer. However, ''Bacillus subtilis'' does not produce 1-deoxymanojirimycin despite the presence of the manojirimycin precursor. Azasugar biosynthesis in ''Commelina communis'' involves C1-C5 cyclisation of the original D-glucose precursor without the subsequent inversion.See also
* Nojirimycin * 1-Deoxygalactonojirimycin, a stereoisomer of 1-deoxynojirimycinReferences
{{DEFAULTSORT:Deoxynojirimycin, 1- Iminosugars