| Identification | Back Directory | [Name]
1,4-DIDEOXY-1,4-IMINO-D-ARABINITOL HYDROCHLORIDE | [CAS]
100991-92-2 | [Synonyms]
1,4-DIDEOXY-1,4-IMINO-D-ARABINITOL HYDROCHLORIDE
2-Hydroxymethyl-3,4-pyrrolidinediol hydrochloride
1,4-Dideoxy-1,4-imino-D-arabinitol hydrochloride enzyme inhibitor
(2R,3R,4R)-3,4-Dihydroxy-2-(hydroxymethyl)pyrrolidine hydrochloride
3,4-Pyrrolidinediol, 2-(hydroxymethyl)-, hydrochloride, (2R,3R,4R)- | [Molecular Formula]
C5H12ClNO3 | [MDL Number]
MFCD03427380 | [MOL File]
100991-92-2.mol | [Molecular Weight]
169.61 |
| Chemical Properties | Back Directory | [Melting point ]
110-112 °C(Solv: ethyl ether (60-29-7); methanol (67-56-1)) | [storage temp. ]
2-8°C | [solubility ]
DMSO: 10 mg/ml; PBS (pH 7.2): 1 mg/ml | [form ]
A crystalline solid | [Water Solubility ]
water: 19.60-20.40mg/mL, clear, colorless to faintly yellow | [InChI]
1S/C5H11NO3.ClH/c7-2-3-5(9)4(8)1-6-3;/h3-9H,1-2H2;1H/t3-,4-,5-;/m1./s1 | [InChIKey]
PZGVJCJRMKIVLJ-DEVUXVJFSA-N | [SMILES]
Cl.OC[C@H]1NC[C@@H](O)[C@@H]1O |
| Hazard Information | Back Directory | [Description]
1,4-dideoxy-1,4-imino-D-Arabinitol (DAB) is an inhibitor of glycogen phosphorylase, a key enzyme in glycogenolysis. It inhibits glycogenolysis in isolated liver cells (IC50 = 1.0 μM) and in homogenates of cerebral cortex and cerebellum (IC50s = 463 and 383 nM, respectively). DAB is used to inhibit glycogenolysis, in liver and in brain, in various animal models. | [Uses]
1,4-Dideoxy-1,4-imino-D-arabinitol hydrochloride has been used as an α-glucosidase (GAA) inhibitor. | [General Description]
1,4-Dideoxy-1,4-imino-D-arabinitol is a naturally occurring pyrrolidine alkaloid. It is found in Arachniodes standishii and Angylocalyx boutiqueanus. | [Biochem/physiol Actions]
Inhibitor of glycogen phosphorylase and α-glucosidases. | [References]
[1] B. ANDERSEN N W. The effect of glucose on the potency of two distinct glycogen phosphorylase inhibitors.[J]. The Ukrainian Biochemical Journal, 2002, 13 1: 443-450. DOI: 10.1042/bj20020153
[2] B. ANDERSEN. Inhibition of glycogenolysis in primary rat hepatocytes by 1, 4-dideoxy-1,4-imino-D-arabinitol.[J]. The Ukrainian Biochemical Journal, 1999, 17 1: 545-550. DOI: 10.1042/bj3420545
[3] ANNE B. WALLS. Characterization of 1,4-dideoxy-1,4-imino-d-arabinitol (DAB) as an inhibitor of brain glycogen shunt activity[J]. Journal of Neurochemistry, 2008, 105 4: 1462-1470. DOI: 10.1111/j.1471-4159.2008.05250.x
[4] KELD FOSGERAU . Kinetic and Functional Characterization of 1,4-Dideoxy-1,4-imino-d-arabinitol: A Potent Inhibitor of Glycogen Phosphorylase with Anti-hyperglyceamic Effect in ob/ob Mice[J]. Archives of biochemistry and biophysics, 2000, 380 2: Pages 274-284. DOI: 10.1006/abbi.2000.1930
[5] GIBBS M. Role of Glycogenolysis in Memory and Learning: Regulation by Noradrenaline, Serotonin and ATP[J]. Frontiers in Integrative Neuroscience, 2016, 9 1. DOI: 10.3389/fnint.2015.00070
[6] NEPHTALI MARINA. Brainstem hypoxia contributes to the development of hypertension in the spontaneously hypertensive rat.[J]. ACS Applied Nano Materials, 2015: 775-783. DOI: 10.1161/hypertensionaha.114.04683 |
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