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C3784

Castanospermine

Name: Castanospermine
Brand: SIGMA

≥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:

79831-76-8

Molecular Weight:

189.21

PubChem Substance ID:

24892642

UNSPSC Code:

12352200

Beilstein/REAXYS Number:

3588654

MDL number:

MFCD00017555

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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

Regulatory Information

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Diastereoselective nitrenium ion-mediated cyclofunctionalization: total synthesis of (+)-castanospermine.

Edward G Bowen et al.

Organic letters, 12(22), 5330-5333 (2010-10-23)

The asymmetric total synthesis of the α-glucosidase inhibitor (+)-castanospermine is reported. The central theme in our approach to this polyhydroxylated alkaloid is the simultaneous generation of the piperidine ring and the C-1/8a erythro stereodiad through the diastereoselective, oxamidation of an

Effects of the anti-inflammatory compounds castanospermine, mannose-6-phosphate and fucoidan on allograft rejection and elicited peritoneal exudates.

M R Bartlett et al.

Immunology and cell biology, 72(5), 367-374 (1994-10-01)

The glycoprotein processing inhibitor castanospermine (CS) and the monosaccharide mannose-6-phosphate (M6P), as well as some sulfated polysaccharides (SPS), have been shown to inhibit inflammation in rat models of experimental autoimmune encephalomyelitis and adjuvant-induced arthritis. Here, the anti-inflammatory effects of these

Inhibition of the exo-beta-D-glucosaminidase CsxA by a glucosamine-configured castanospermine and an amino-australine analogue.

Benjamin Pluvinage et al.

Organic & biomolecular chemistry, 7(20), 4169-4172 (2009-10-02)

The synthesis of amino-derivatives of castanospermine and australine and their characterisation as inhibitors of the exo-beta-D-glucosaminidase CsxA through enzyme kinetics and X-ray structural analysis is described.

Glycosidase inhibition by ring-modified castanospermine analogues: tackling enzyme selectivity by inhibitor tailoring.

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

Asymmetric synthesis of (+)-castanospermine through enol ether metathesis-hydroboration/oxidation.

Julien Ceccon et al.

Organic & biomolecular chemistry, 7(10), 2029-2031 (2009-05-08)

An asymmetric synthesis of (+)-castanospermine is presented in which enol ether metathesis-hydroboration/oxidation is used for stereoselective installation of the trans-trans hydroxyl groups on the piperidine ring of the alkaloid.

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Global Trade Item Number

SKU	GTIN
C3784-1MG	04061833486382
C3784-5MG	04061833269817

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