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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
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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.[1]

Application

1,4-Dideoxy-1,4-imino-D-arabinitol hydrochloride has been used as an α-glucosidase (GAA) inhibitor.[2]

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

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    Certificates of Analysis (COA)

    Lot/Batch Number
    0000272648
    0000243365
    0000272648
    0000243365
    0000213724

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    Tetrahedron Letters, 42, 5685-5685 (1986)
    A new resorufin-based $\alpha$-glucosidase assay for high-throughput screening
    Motabar O, et al.
    Analytical Biochemistry, 390(1), 79-84 (2009)
    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
    E Vezzoli et al.
    Cerebral cortex (New York, N.Y. : 1991), 30(4), 2114-2127 (2019-12-07)
    Long-term memory formation (LTM) is a process accompanied by energy-demanding structural changes at synapses and increased spine density. Concomitant increases in both spine volume and postsynaptic density (PSD) surface area have been suggested but never quantified in vivo by clear-cut
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