C3784
Castanospermine
≥94% (GC), BioUltra, from Castanospermum australe seeds
Synonym(s):
(1S,6S,7R,8R,8aR)-1,6,7,8-Tetrahydroxyoctahydroindolizidine, (1S,6S,7R,8R,8aR)-Octahydro-1,6,7,8-indolizinetetrol
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About This Item
Empirical Formula (Hill Notation):
C8H15NO4
CAS Number:
Molecular Weight:
189.21
PubChem Substance ID:
UNSPSC Code:
12352200
Beilstein/REAXYS Number:
3588654
MDL number:
biological source
Castanospermum australe seeds
product line
BioUltra
assay
≥94% (GC)
form
powder
mp
212-215 °C (dec.)
solubility
1 M HCl: 20 mg/mL, clear, colorless to faintly yellow
storage temp.
2-8°C
SMILES string
O[C@H]1CCN2C[C@H](O)[C@@H](O)[C@H](O)[C@@H]12
InChI
1S/C8H15NO4/c10-4-1-2-9-3-5(11)7(12)8(13)6(4)9/h4-8,10-13H,1-3H2/t4-,5-,6+,7+,8+/m0/s1
InChI key
JDVVGAQPNNXQDW-TVNFTVLESA-N
Biochem/physiol Actions
α-glucosidase Inhibitor
Storage Class
13 - Non Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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Product Information Sheet
Matilde Aguilar-Moncayo et al.
Organic & biomolecular chemistry, 7(13), 2738-2747 (2009-06-18)
Synthesis of a panel of iso(thio)urea-type ring-modified castanospermine analogues bearing a freely mutarotating pseudoanomeric hydroxyl group results in tight-binding beta-glucosidase inhibitors with unusual binding signatures; the presence of an N-octyl substituent imparts a remarkable anomeric selectivity, promoting strong binding of
Thomas Jensen et al.
The Journal of organic chemistry, 74(22), 8886-8889 (2009-10-28)
A nine-step synthesis of (+)-castanospermine has been accomplished in 22% overall yield from methyl alpha-D-glucopyranoside. The key transformations involve a zinc-mediated fragmentation of benzyl-protected methyl 6-iodoglucopyranoside, ring-closing olefin metathesis, and strain-release transannular cyclization to afford the indolizidine skeleton of the
Tomohisa Kato et al.
Analytical biochemistry, 405(1), 103-108 (2010-06-24)
Saccharide primers, such as dodecyl beta-lactoside (Lac-C12), are unique artificial precursors of glycolipid synthesis. In culture media supplemented with saccharide primers, they are taken up by the cells in the culture media and glycosylated by cellular glycosyltransferases in the Golgi