CAS 59920-31-9

2,5-Dideoxy-2,5-imino-D-mannitol

Description:

2,5-Dideoxy-2,5-imino-D-mannitol, with the CAS number 59920-31-9, is a synthetic compound that belongs to the class of imino sugars. It is characterized by the presence of both hydroxyl and imino functional groups, which contribute to its unique chemical properties. This compound is a derivative of D-mannitol, a sugar alcohol, and exhibits structural features that make it a potential inhibitor of glycosidases, enzymes that play a crucial role in carbohydrate metabolism. The imino group introduces a nitrogen atom into the structure, which can influence its biological activity and solubility. 2,5-Dideoxy-2,5-imino-D-mannitol has garnered interest in medicinal chemistry for its potential applications in treating conditions related to glycosylation disorders and diabetes. Its stability, reactivity, and ability to mimic natural substrates make it a valuable compound for research in biochemistry and pharmacology. However, detailed studies on its pharmacokinetics and toxicity are essential for understanding its therapeutic potential.

Formula: C₆H₁₃NO₄

InChI: InChI=1S/C6H13NO4/c8-1-3-5(10)6(11)4(2-9)7-3/h3-11H,1-2H2/t3-,4-,5-,6-/m1/s1

InChI key: InChIKey=PFYHYHZGDNWFIF-KVTDHHQDSA-N

SMILES: C(O)[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)N1

Synonyms:

• (2R,3R,4R,5R)-2,5-bis(hydroxymethyl)pyrrolidine-3,4-diol
• (2R,3R,4R,5R)-3,4-Dihydroxy-2,5-pyrrolidinedimethanol
• 2(R),5(R)-Bis(hydroxymethyl)-3(R),4(R)-dihydroxypyrrolidine
• 2,5-Bis(Hydroxymethyl)Pyrrolidine-3,4-Diol
• 2,5-Dideoxy-2,5-imino-<span class="text-smallcaps">D</span>-mannitol
• 2,5-Dideoxy-2,5-imino-D-mannitol
• 2,5-Pyrrolidinedimethanol, 3,4-dihydroxy-, (2R,3R,4R,5R)-
• 2,5-Pyrrolidinedimethanol, 3,4-dihydroxy-, [2R-(2α,3β,4α,5β)]-
• Dmdp
• α-Glucosidase

(2R,3R,4R,5R)-2,5-Bis(hydroxymethyl)pyrrolidine-3,4-diol

CAS: 59920-31-9

Formula: C₆H₁₃NO₄

Purity: 98%

Color and Shape: Solid

Molecular weight: 163.1717

Ref: IN-DA019FTO

2,5-Anhydro-2,5-imino-D-mannitol

CAS: 59920-31-9

Molecular weight: 163.17

Ref: 7W-GC1249

2,5-Dideoxy-2,5-imino-D-mannitol

Controlled Product

CAS: 59920-31-9

Stability Hygroscopic
Applications A glucosidase inhibitor.
References Fellows, L.E.: Pestic. Sci., 17, 602 (1986)

Formula: C₆H₁₃NO₄

Color and Shape: Off White Solid

Molecular weight: 163.17

Ref: TR-D440000

2,5-Dideoxy-2,5-imino-D-mannitol

CAS: 59920-31-9

2,5-Dideoxy-2,5-imino-D-mannitol is an iminosugar compound, which is a synthetic derivative with potent glycosidase inhibitory properties. The compound, typically synthesized through complex organic processes, acts by mimicking the transition state of natural substrates in glycosidases, thereby inhibiting their enzymatic activity. This mode of action involves binding to the active site of glycosidase enzymes, preventing the normal hydrolysis of glycosidic bonds.

Formula: C₆H₁₃NO₄

Purity: Min. 95%

Color and Shape: Powder

Molecular weight: 163.17 g/mol

Ref: 3D-MD04702

2,5-Anhydro-2,5-imino-D-mannitol

Controlled Product

CAS: 59920-31-9

Applications Many pyrrolidines are powerful inhibitors of glycohydrolases, enzymes responsible for cleavage of glycosidic bonds, glycoprotein processing and the gastrointestinal breakdown of dietary carbohydrates. These compounds are charged at physiological pH and are believed to associate with acidic amino acids at the active site. Inhibition of glycohydrolases could be of therapeutic value for the treatment of viral infections, cancer, diabetes, and obesity.
References Fellows, L.E., et al.: J. Chem. Brit., 287, (1987), Elbein, A.D.: Annu. Rev. Biochem., 56, 497 (1987), Fleet, G.W., et al.: J. Chem. Brit., 287, (1989) Baxter, E.W., et al.: J. Org. Chem., 59, 3175 (1994); Tyms, A.S. et al. Lancet 1025, (1987); Spearman, M.A. et al. Expt. Cell Res. 168, 116 (1987); Horii, S. et al. J. Med. Chem. 29, 1038 (1986), Minami, Y., et al.: Bioorg. Med. Chem., 16, 2734 (2008),

Formula: C₆H₁₃NO₄

Color and Shape: Neat

Molecular weight: 163.17

Ref: TR-A648350