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D1542

Sigma-Aldrich

1,4-Dideoxy-1,4-imino-D-arabinitol hydrochloride

enzyme inhibitor

Synonym(s):

2-Hydroxymethyl-3,4-pyrrolidinediol hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C5H11NO3 · HCl
CAS Number:
100991-92-2
Molecular Weight:
169.61
MDL number:
MFCD03427380
UNSPSC Code:
12352202
PubChem Substance ID:
24278359
NACRES:
NA.77

Quality Level

200

assay

≥98% (TLC)

form

solid

storage condition

under inert gas

solubility

water: 19.60-20.40 mg/mL, clear, colorless to faintly yellow

storage temp.

2-8°C

SMILES string

Cl.OC[C@H]1NC[C@@H](O)[C@@H]1O

InChI

1S/C5H11NO3.ClH/c7-2-3-5(9)4(8)1-6-3;/h3-9H,1-2H2;1H/t3-,4-,5-;/m1./s1

InChI key

PZGVJCJRMKIVLJ-DEVUXVJFSA-N

Gene Information

human ... PYGB(5834) , PYGBL(5835) , PYGL(5836) , PYGM(5837)
mouse ... Gaa(14387) , Glb1(12091) , Treh(58866)
rat ... Man2a1(25478) , Pygl(64035) , Si(25588)

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.

Application

1,4-Dideoxy-1,4-imino-D-arabinitol hydrochloride has been used as an α-glucosidase (GAA) inhibitor.

Biochem/physiol Actions

Inhibitor of glycogen phosphorylase and α-glucosidases.

Caution

Extremely hygroscopic, store and handle under argon

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A new resorufin-based $\alpha$-glucosidase assay for high-throughput screening
Motabar O, et al.
Analytical Biochemistry, 390(1), 79-84 (2009)
Tetrahedron Letters, 42, 5685-5685 (1986)
The synthesis from d-xylose of the potent and specific enantiomeric glucosidase inhibitors, 1, 4-dideoxy-1, 4-imino-d-arabinitol and 1, 4-dideoxy-1, 4-imin
Fleet GWJ and Smith PW
Tetrahedron, 42(20), 5685-5692 (1986)
Ze Fan et al.
Neuroscience bulletin, 36(12), 1513-1523 (2020-10-14)
General anesthesia severely affects the metabolites in the brain. Glycogen, principally stored in astrocytes and providing the short-term delivery of substrates to neurons, has been implicated as an affected molecule. However, whether glycogen plays a pivotal role in modulating anesthesia-arousal
Omid Motabar et al.
Analytical biochemistry, 390(1), 79-84 (2009-04-18)
Mutations in alpha-glucosidase cause accumulation of glycogen in lysosomes, resulting in Pompe disease, a lysosomal storage disorder. Small molecule chaperones that bind to enzyme proteins and correct the misfolding and mistrafficking of mutant proteins have emerged as a new therapeutic
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