CAS 100937-52-8

1,4-dideoxy-1,4-imino-D-arabinitol

Description:

1,4-Dideoxy-1,4-imino-D-arabinitol is a chemical compound that belongs to the class of iminosugars, which are characterized by their structural similarity to sugars but contain nitrogen in place of one or more oxygen atoms. This compound is notable for its potential biological activity, particularly as an inhibitor of glycosidases, enzymes that play a crucial role in carbohydrate metabolism. Its structure features a dideoxy configuration, indicating the absence of hydroxyl groups at specific positions, which contributes to its unique properties and reactivity. The imino group introduces a nitrogen atom into the sugar framework, which can influence its interaction with biological targets. 1,4-Dideoxy-1,4-imino-D-arabinitol has been studied for its potential therapeutic applications, particularly in the context of diabetes and viral infections, due to its ability to modulate glycosylation processes. As with many iminosugars, its solubility and stability in biological systems are important factors that affect its efficacy and potential use in medicinal chemistry.

Formula: C₅H₁₁NO₃

InChI: InChI=1/C5H11NO3/c7-2-3-5(9)4(8)1-6-3/h3-9H,1-2H2/t3-,4-,5-/m1/s1

SMILES: C1[C@H]([C@@H]([C@@H](CO)N1)O)O

Synonyms:

• (2R,3R,4R)-2-(hydroxymethyl)pyrrolidine-3,4-diol
• 1,4-Dideoxy-1,4-Imino-D-Mannitol

(2R,3R,4R)-2-(Hydroxymethyl)pyrrolidine-3,4-diol

CAS: 100937-52-8

Formula: C₅H₁₁NO₃

Molecular weight: 133.1457

Ref: IN-DA000391

1,4-Dideoxy-1,4-Imino-D-Arabinitol

CAS: 100937-52-8

Formula: C₅H₁₁NO₃

Molecular weight: 133.15

Ref: 4Z-A-170001

1,4-Dideoxy-1,4-imino-D-Arabinitol-d2

CAS: 100937-52-8

Formula: C₅H₉D₂NO₃

Molecular weight: 135.16

Ref: 4Z-A-170004

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

CAS: 100937-52-8

1,4-Dideoxy-1,4-imino-D-arabinitol (1,4DA) is an inhibitor of glycolysis that has potent inhibitory activity against the enzyme phosphofructokinase. It has been shown to decrease cellular ATP levels in rat liver and kidney tissues. 1,4DA also inhibits urine production by inhibiting the conversion of fructose to glucose in the kidney. This compound is a racemic mixture with two enantiomers: R and S. The pharmacokinetics of 1,4DA have been studied in rats and humans using a model system. In rats, 1,4DA was absorbed rapidly and excreted unchanged in the urine. In humans, this drug was well absorbed after oral administration and metabolized mainly by hydrolysis to form 1,4-dideoxyfructose (Fru).

Formula: C₅H₁₁NO₃

Purity: Min. 95%

Molecular weight: 133.15 g/mol

Ref: 3D-MD31527