1-deoxynojirimycin on:
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1-Deoxynojirimycin (DNJ or 1-DNJ), also called duvoglustat or moranolin, is an
alpha-glucosidase inhibitor Alpha-glucosidase inhibitors (AGIs) are oral anti-diabetic drugs used for diabetes mellitus type 2 that work by preventing the digestion of carbohydrates (such as starch and table sugar). Carbohydrates are normally converted into simple sugars ( ...
, most commonly found in mulberry leaves. Although it can be obtained in small quantities by brewing an herbal tea
Herbal teas, also known as herbal infusions and less commonly called tisanes (UK and US , US also ), are beverages made from the infusion or decoction of herbs, spices, or other plant material in hot water. Oftentimes herb tea, or the plain term ...
from mulberry leaves, interest in commercial production has led to research on developing mulberry tea higher in DNJ, and on alternate routes of production, such as via ''Bacillus
''Bacillus'' (Latin "stick") is a genus of Gram-positive, rod-shaped bacteria, a member of the phylum '' Bacillota'', with 266 named species. The term is also used to describe the shape (rod) of other so-shaped bacteria; and the plural ''Bacill ...
'' species.
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