CAS 105990-41-8

1,4-Dideoxy-1,4-imino-D-ribitol

Description:

1,4-Dideoxy-1,4-imino-D-ribitol, with the CAS number 105990-41-8, is a synthetic compound that belongs to the class of iminosugars. It is characterized by the presence of a ribitol backbone, which is a sugar alcohol derived from ribose, with both the 1 and 4 positions modified to contain imino groups instead of hydroxyl groups. This structural modification imparts unique biochemical properties, particularly in its ability to inhibit certain glycosidases and glycosyltransferases, making it of interest in medicinal chemistry and biochemistry. The compound is typically a white to off-white solid and is soluble in water, which facilitates its biological activity. Its potential applications include antiviral and antidiabetic therapies, as it can interfere with carbohydrate metabolism and viral replication processes. As with many iminosugars, its mechanism of action is linked to the modulation of glycoprotein synthesis and function, highlighting its significance in research related to carbohydrate chemistry and therapeutic development.

Formula: C₅H₁₁NO₃

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

InChI key: InChIKey=OQEBIHBLFRADNM-MROZADKFSA-N

SMILES: C(O)[C@@H]1[C@@H](O)[C@@H](O)CN1

Synonyms:

• (2R,3R,4S)-2-(Hydroxymethyl)-3,4-pyrrolidinediol
• (2R,3R,4S)-2-(hydroxymethyl)pyrrolidine-3,4-diol
• 1,4-Dideoxy-1,4-imino-<span class="text-smallcaps">D</span>-ribitol
• 1,4-Dideoxy-1,4-imino-D-ribitol
• 3,4-Pyrrolidinediol, 2-(hydroxymethyl)-, (2R-(2a,3b,4b))-
• DRib
• 3,4-Pyrrolidinediol, 2-(hydroxymethyl)-, (2R,3R,4S)-

1,4-Dideoxy-1,4-imino-D-ribitol

CAS: 105990-41-8

1,4-Dideoxy-1,4-imino-D-ribitol is a polyhydroxylated pyrrolidine alkaloid isolated from the roots of mulberry trees (Morus alba) and from the bark of leguminous plants (Angylocalyx pynaertii).  Due to its structure it has been looked at as enzyme inhibitors that mimic glycoside and nucleoside substrates.  It was found to be a potent inhibitor of lysosomal β-mannosidase and eukaryotic DNA polymerases.

Formula: C₅H₁₁NO₃

Purity: Min. 95%

Molecular weight: 133.15 g/mol

Ref: 3D-MD16163