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M1777

Sigma-Aldrich

N-Methyl-1-deoxynojirimycin

≥98%

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Synonym(s):
1,5-Dideoxy-1,5-imino-1-methyl-D-sorbitol
Empirical Formula (Hill Notation):
C7H15NO4
CAS Number:
69567-10-8
Molecular Weight:
177.20
Beilstein/REAXYS Number:
1524564
MDL number:
MFCD00133609
UNSPSC Code:
12352200
PubChem Substance ID:
24896690
NACRES:
NA.32

biological source

synthetic (organic)

Quality Level

200

assay

≥98%

form

powder

solubility

methanol: 10 mg/mL, clear, colorless

antibiotic activity spectrum

viruses

mode of action

enzyme | inhibits

storage temp.

−20°C

SMILES string

CN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO

InChI

1S/C7H15NO4/c1-8-2-5(10)7(12)6(11)4(8)3-9/h4-7,9-12H,2-3H2,1H3/t4-,5+,6-,7-/m1/s1

InChI key

AAKDPDFZMNYDLR-XZBKPIIZSA-N

Gene Information

mouse ... Gaa(14387) , Glb1(12091) , Treh(58866)
rat ... Man2a1(25478) , Si(497756)

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Related Categories

General description

Chemical structure: glucosamine

Biochem/physiol Actions

Interferes with metabolism of N-linked glycoproteins by inhibition of glucosidase.

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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Diego A Caraballo et al.
G3 (Bethesda, Md.), 10(2), 755-768 (2019-12-05)
UDP- glucose: glycoprotein glucosyltransferase (UGGT) is a protein that operates as the gatekeeper for the endoplasmic reticulum (ER) quality control mechanism of glycoprotein folding. It is known that vertebrates and Caenorhabditis genomes harbor two uggt gene copies that exhibit differences
P F Daniel et al.
American journal of medical genetics, 42(4), 586-592 (1992-02-15)
In agreement with reports from other laboratories, we have shown that patients with the juvenile or late infantile forms of neuronal ceroid-lipofuscinosis (NCL) have greatly increased levels (5-fold to 20-fold) of dolichyl pyrophosphoryl oligosaccharides in their cerebral gray matter. Oligosaccharides
J C Ridruejo et al.
Biochimica et biophysica acta, 993(2-3), 179-185 (1989-12-08)
Castanospermine, 1-deoxynojirimycin, and N-methyl-1-deoxynojirimycin, three well-characterized inhibitors of the glucosidases involved in the processing of N-linked oligosaccharides, did not affect the biosynthesis or the secretion of exoglucanases (EC 3.2.1.58) from Saccharomyces cerevisiae and Candida albicans but inhibited the activity itself.
D J Wu et al.
Japanese circulation journal, 65(7), 673-677 (2001-07-12)
N-methyl-1-deoxynojirimycin (NMDN), an a-glucosidase inhibitor, reduces myocardial infarct size by reducing the glycogenolytic rate through inhibition of the alpha-1,6-glucosidase of glycogen-debranching enzyme in the heart, in addition to possessing an antihyperglycemic action by blocking alpha-1,4-glucosidase in the intestine. Ischemic preconditioning
G C Trudel et al.
Biochemistry and cell biology = Biochimie et biologie cellulaire, 66(10), 1119-1125 (1988-10-01)
It has recently been reported that the glucosidase I inhibitor, N-methyl-1-deoxynojirimycin (MDJN), inhibits myoblast fusion whereas the mannosidase inhibitor, 1-deoxymannojirimycin (ManDJN), has no effect on fusion. We now report that bromoconduritol, which is an active-site-directed covalent inhibitor of glucosidase II
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