All Photos(1)

H9632

Sigma-Aldrich

(2R,5R)-Bis(hydroxymethyl)-(3R,4R)-dihydroxypyrrolidine

Synonym(s):
2,5-Dideoxy-2,5-imino-D-mannitol, DMDP
Empirical Formula (Hill Notation):
C6H13NO4
CAS Number:
Molecular Weight:
163.17
MDL number:
PubChem Substance ID:

storage temp.

2-8°C

SMILES string

OCC1NC(CO)C(O)C1O

Gene Information

Biochem/physiol Actions

Reversible inhibitor of D-glucosidase and invertase.

Certificate of Analysis

Certificate of Origin

A D Elbein et al.
The Journal of biological chemistry, 259(20), 12409-12413 (1984-10-25)
2,5-Dihydroxymethyl-3,4-dihydroxypyrrolidine (DMDP) is a pyrrolidine alkaloid that was isolated from the plant, Lonchocarpus sericeus. In the present study, DMDP was tested as an inhibitor of glycoprotein processing. MDCK cells were infected with influenza virus and the virus was raised in...
C G Barker et al.
The Biochemical journal, 235(1), 151-158 (1986-04-01)
A kitten with clinical and morphological symptoms of a neurovisceral lysosomal-storage disease has been shown to have a marked deficiency of acidic beta-D-galactosidase in the brain, kidney and spleen. Chromatography on concanavalin A-Sepharose and inhibition studies with 2,5-dihydroxymethyl-3,4-dihydroxypyrrolidine, a selective...
Tanja M Wrodnigg et al.
Bioorganic & medicinal chemistry, 12(13), 3485-3495 (2004-06-10)
A range of new C-1 modified derivatives of the powerful glucosidase inhibitor 2,5-dideoxy-2,5-imino-D-mannitol has been synthesised and their biological activities probed with the beta-glucosidase from Agrobacterium sp. Ki values are compared with those of previously prepared close relatives. Findings suggest...
Atsushi Kato et al.
Phytochemistry, 69(5), 1261-1265 (2008-01-15)
Chromatographic separation of the 50% aqueous EtOH extract of the leaves of the African medicinal tree Baphia nitida resulted in isolation of 10 iminosugars. The plant contained 2R,5R-dihydroxymethyl-3R,4R-dihydroxypyrrolidine (DMDP) as a major alkaloid. The structure of a new alkaloid was...
Timothy J Donohoe et al.
Organic letters, 5(7), 999-1002 (2003-03-28)
[reaction: see text] The partial reduction of electron-deficient 2,5-disubstituted pyrroles has been developed into a flexible procedure that gives control of relative stereochemistry by variation of the reduction conditions. After the reaction, the pyrroline products were dihydroxylated at C-3,4 to...

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