CAS 80312-32-9

(2R,3R,4R,5S)-4,5-Dihydroxy-2-(hydroxymethyl)-3-piperidinyl α-D-glucopyranoside

Description:

The chemical substance known as (2R,3R,4R,5S)-4,5-Dihydroxy-2-(hydroxymethyl)-3-piperidinyl α-D-glucopyranoside, with the CAS number 80312-32-9, is a glycosylated compound featuring a piperidine ring and a glucopyranoside moiety. This compound is characterized by its multiple hydroxyl groups, which contribute to its hydrophilicity and potential for forming hydrogen bonds, enhancing its solubility in polar solvents. The stereochemistry indicated by the (2R,3R,4R,5S) configuration suggests specific spatial arrangements of the substituents, which can influence its biological activity and interactions with other molecules. Such compounds are often studied for their potential applications in pharmaceuticals, particularly in the context of drug design and development, due to their ability to mimic natural substrates or act as inhibitors in biochemical pathways. Additionally, the presence of the piperidine structure may impart unique properties, such as increased stability or specific receptor binding capabilities. Overall, this compound represents a complex structure with potential significance in medicinal chemistry and biochemistry.

Formula: C₁₂H₂₃NO₉

InChI: InChI=1S/C12H23NO9/c14-2-4-11(7(17)5(16)1-13-4)22-12-10(20)9(19)8(18)6(3-15)21-12/h4-20H,1-3H2/t4-,5+,6-,7-,8-,9+,10-,11-,12-/m1/s1

InChI key: InChIKey=GNVIYGFSOIHFHK-NIKVEEOSSA-N

SMILES: O([C@@H]1[C@@H](CO)NC[C@H](O)[C@H]1O)[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O

Synonyms:

• α-D-Glucopyranoside, (2R,3R,4R,5S)-4,5-dihydroxy-2-(hydroxymethyl)-3-piperidinyl
• 1,5-Dideoxy-4-O-α-D-glucopyranosyl-1,5-imino-D-glucitol
• α-D-Glucopyranoside, 4,5-dihydroxy-2-(hydroxymethyl)-3-piperidinyl, [2R-(2α,3β,4α,5β)]-
• (2R,3R,4R,5S)-4,5-Dihydroxy-2-(hydroxymethyl)-3-piperidinyl α-D-glucopyranoside
• 4-O-α-D-Glucopyranosylmoranoline

4-O-α-D-Glucopyranosylmoranoline

Controlled Product

CAS: 80312-32-9

Applications An α-glucosidase inhibitor. May also prove to be an effective oral anti-diabetic agent.
References Yoshikuni, Y., et al.: Chem. Pharm. Bull., 37, 106 (1989), Ezure, Y., et al.: Agric. Biol. Chem., 53, 61 (1989), Kunikata, T., et al.: Biosci., Biotechnol., Biochem., 60, 1104 (1996),

Formula: C₁₂H₂₃NO₉

Color and Shape: Neat

Molecular weight: 325.31

Ref: TR-G450000

4-O-(α-D-Glucopyranosyl) moranoline

CAS: 80312-32-9

4-O-(α-D-Glucopyranosyl) moranoline is an iminosugar that functions as an effective glycosidase inhibitor, specifically targeting enzymes involved in carbohydrate metabolism. It is derived from natural sources such as mulberry leaves, where it is produced as a defense compound against herbivores. This substance interferes with the activity of α-glucosidases by mimicking the transition state of the glycosidic bond cleavage, thereby preventing the breakdown of complex carbohydrates into glucose.

Formula: C₁₂H₂₃NO₉

Purity: Min. 95%

Color and Shape: Powder

Molecular weight: 325.32 g/mol

Ref: 3D-OG04734