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D1542

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

Name: 1,4-Dideoxy-1,4-imino-<SC>D</SC>-arabinitol hydrochloride
Brand: SIGMA

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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)

A new resorufin-based alpha-glucosidase assay for high-throughput screening.

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

Glycogenolysis in Acquired Glioma Resistance to Temozolomide: A Role for the [Ca2+]i-dependent Activation of Na,K-ATPase/ERK1/2 Signaling.

Junnan Xu et al.

Frontiers in pharmacology, 9, 873-873 (2018-08-23)

Understanding the mechanistic basis for temozolomide (TMZ)-induced glioma resistance is an important obstacle in developing an effective form of chemotherapy for this type of tumor. Glycogenolysis is known to play an essential role in cellular proliferation and potassium homeostasis and

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