D9305
1-Deoxynojirimycin hydrochloride
Synonym(s):
1,5-Dideoxy-1,5-imino-D-sorbitol hydrochloride
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About This Item
Empirical Formula (Hill Notation):
C6H13NO4 · HCl
CAS Number:
Molecular Weight:
199.63
UNSPSC Code:
12352201
NACRES:
NA.32
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
3563225
InChI
1S/C6H13NO4.ClH/c8-2-3-5(10)6(11)4(9)1-7-3;/h3-11H,1-2H2;1H/t3-,4+,5-,6-;/m1./s1
SMILES string
Cl[H].OC[C@H]1NC[C@H](O)[C@@H](O)[C@@H]1O
InChI key
ZJIHMALTJRDNQI-VFQQELCFSA-N
assay
≥98% (TLC)
form
powder
solubility
water: 19.60-20.40 mg/mL, clear, colorless
antibiotic activity spectrum
viruses
mode of action
enzyme | inhibits
storage temp.
2-8°C
Quality Level
Gene Information
human ... GAA(2548)
General description
Chemical structure: glucosamine
Application
1-Deoxynojirimycin hydrochloride has been used
- to study its effects on the loss-of-function of N-glycosylation pathway on hair cell regeneration
- as an endoplasmic reticulum (ER) α-glucosidase I and II inhibitor to study its effects on TMED3-cystic fibrosis transmembrane conductance regulator (CFTR) interaction
- as an insect trehalase inhibitor in TREH inhibition bioassay
Biochem/physiol Actions
α-Glucosidase inhibitor
1-Deoxynojirimycin (DNJ) is a naturally occurring alkaloid azasugar or iminosugar. It is observed in mulberry leaves, Commelina communis, and bacterial strains including Bacillus and Streptomyces species. DNJ acts as an α-glucosidase inhibitor and exhibits anti-viral anti-diabetic, anti-inflammatory, anti-obesity, and antioxidant properties.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Regulatory Information
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Marc C Patterson et al.
Orphanet journal of rare diseases, 8, 12-12 (2013-01-18)
Niemann-Pick disease type C (NP-C) is a rare neurovisceral disease characterized by progressive neurodegeneration and premature death. We report data recorded at enrolment in an ongoing international NP-C registry initiated in September 2009 to describe disease natural history, clinical course
Gitanjali Bhushan et al.
Frontiers in microbiology, 11, 531-531 (2020-05-07)
Zika virus (ZIKV), a vector-borne virus of the family Flaviviridae, continues to spread and remains a significant global public health threat. Currently, there are no approved vaccines or antivirals against ZIKV. We investigated the anti-ZIKV ability of three iminosugars with
Timothy M Cox et al.
Orphanet journal of rare diseases, 7, 102-102 (2012-12-29)
Previous studies have provided equivocal data on the use of miglustat as maintenance therapy in Gaucher disease type 1. We report findings from a clinical trial evaluating the effects of miglustat treatment in patients with stable type 1 Gaucher disease
I Neverova et al.
Analytical biochemistry, 222(1), 190-195 (1994-10-01)
A spectrophotometric assay for glucosidase I using the synthetic trisaccharide alpha-D-Glc 1-->2 alpha-D-Glc 1-->3 alpha-D-Glc-O(CH2)8COOCH3 is reported. The terminal glucose is released from the substrate by the enzyme and quantitated using glucose oxidase, peroxidase, and o-dianisidine. The trisaccharide is specific
Stephen G Davies et al.
Organic letters, 15(8), 2042-2045 (2013-04-11)
The asymmetric syntheses of (-)-1-deoxymannojirimycin and (+)-1-deoxyallonojirimycin are described herein. The ring-closing iodoamination of two epimeric bishomoallylic amines to give the corresponding 5-iodomethylpyrrolidines was followed by in situ ring-expansion to give two diastereoisomerically pure (>99:1 dr) cyclic carbonates. Subsequent deprotection
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