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Key Documents

H9632

Sigma-Aldrich

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

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C6H13NO4
CAS Number:
Molecular Weight:
163.17
MDL number:
UNSPSC Code:
12352200
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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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
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
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
E A Bruyneel et al.
Journal of cell science, 95 ( Pt 2), 279-286 (1990-02-01)
Cell surface glycans are believed to play a role in tumour invasion and metastasis. Yet, we have previously shown that the inhibitors of N-linked glycan processing swainsonine (SW) and 1-deoxynojirimycin (dNM) did not prevent invasion of chick heart fragments by
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

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