Isofagomine - CAS 169105-89-9
Catalog number: 169105-89-9
Category: Inhibitor
Please be kindly noted products are not for therapeutic use. We do not sell to patients.
Molecular Formula:
C6H13NO3
Molecular Weight:
147.17
COA:
Inquire
Targets:
Others
Description:
Isofagomine, an imino pyranose compound, has been found to be a glucosylceramidase stimulant and could exhibit activity in Gaucher's disease.
Purity:
98%
Appearance:
Yellow low-melting solid
Synonyms:
(3R,4R,5R)-5-(hydroxymethyl)piperidine-3,4-diol; Isofagomine; Iso-Fagomine
Storage:
Store in a cool and dry place and at 0 - 4 °C for short term (days to weeks) or -20 °C for long term (months to years).
MSDS:
Inquire
Quality Standard:
In-house standard
Quantity:
Milligram-Grams
Boiling Point:
317.2ºC at 760mmHg
Density:
1.279 g/cm3
InChIKey:
QPYJXFZUIJOGNX-HSUXUTPPSA-N
InChI:
InChI=1S/C6H13NO3/c8-3-4-1-7-2-5(9)6(4)10/h4-10H,1-3H2/t4-,5-,6-/m1/s1
Canonical SMILES:
C1C(C(C(CN1)O)O)CO
Current Developer:
Amicus Therapeutics
1.Atomic resolution analyses of the binding of xylobiose-derived deoxynojirimycin and isofagomine to xylanase Xyn10A.
Gloster TM;Williams SJ;Roberts S;Tarling CA;Wicki J;Withers SG;Davies GJ Chem Commun (Camb). 2004 Aug 21;(16):1794-5. Epub 2004 Jul 23.
The atomic resolution structures of xylobiose-derived isofagomine and xylobiose-derived deoxynojirimycin in complex with the xylanase Xyn10A from Streptomyces lividans reveal undistorted (4)C(1) chair conformed sugars and, in the case of the deoxynojirimycin analogue, suggest unusual pK(a) changes of the enzyme's catalytic machinery upon binding.
2.Compartmentation of lactate originating from glycogen and glucose in cultured astrocytes.
Sickmann HM;Schousboe A;Fosgerau K;Waagepetersen HS Neurochem Res. 2005 Oct;30(10):1295-304.
Brain glycogen metabolism was investigated by employing isofagomine, an inhibitor of glycogen phosphorylase. Cultured cerebellar and neocortical astrocytes were incubated in medium containing [U-(13C)]glucose in the absence or presence of isofagomine and the amounts and percent labeling of intra- and extracellular metabolites were determined by mass spectrometry (MS). The percent labeling in glycogen was markedly decreased in the presence of isofagomine. Surprisingly, the percent labeling of intracellular lactate was also decreased demonstrating the importance of glycogen turnover. The decrease was limited to the percent labeling in the intracellular pool of lactate, which was considerably lower compared to that observed in the medium in which it was close to 100%. These findings indicate compartmentation of lactate derived from glycogenolysis and that derived from glycolysis. Inhibiting glycogen degradation had no effect on the percent labeling in citrate. However, the percent labeling of extracellular glutamine was slightly decreased in neocortical astrocytes exposed to isofagomine, indicating an importance of glycogen turnover in the synthesis of releasable glutamine. In conclusion, the results demonstrate that glycogen in cultured astrocytes is continuously synthesized and degraded.
3.A new route to diverse 1-azasugars from N-Boc-5-hydroxy-3-piperidene as a common building block.
Ouchi H;Mihara Y;Takahata H J Org Chem. 2005 Jun 24;70(13):5207-14.
A new general method for the synthesis of a variety of 1-azasugars with a nitrogen atom at the anomeric position is described. The readily available chiral N-Boc-5-hydroxy-3-piperidene 3 is transformed to isofagomine (2), homoisofagomine (13), and 5'-deoxyisofagomine (14) via stereoselective epoxidation and regioselective ring-cleavage in a highly stereocontrolled manner. In addition, the synthesis of all four stereoisomers of 3,4,5-trihydroxypiperidines (18-21) classified as 1-azasugar-type glycosidase inhibitors was stereoselectively achieved from the (chiral) piperidene 3.
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CAS 169105-89-9 Isofagomine

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