Castanospermine
Chemical compound
From Wikipedia, the free encyclopedia
Castanospermine is an indolizidine alkaloid first isolated from the seeds of Castanospermum australe.[3] It is a potent inhibitor of some glucosidase enzymes[4] and has antiviral activity in vitro and in mouse models.[5]
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| Names | |
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| Preferred IUPAC name
(1S,6S,7R,8R,8aR)-Octahydroindolizine-1,6,7,8-tetrol | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| DrugBank | |
| ECHA InfoCard | 100.127.469 |
| EC Number |
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| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C8H15NO4 | |
| Molar mass | 189.209 g/mol |
| Appearance | White to off-white solid |
| Melting point | 212 to 215 °C (414 to 419 °F; 485 to 488 K) |
| Soluble | |
| Hazards | |
| GHS labelling: | |
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| Warning | |
| H302, H312, H332 | |
| P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P322, P330, P363, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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The castanospermine derivative celgosivir is an antiviral drug candidate that as of 2009 was in development for possible use in treating hepatitis C virus (HCV) infection.[6]
Biosynthesis
L-Lysine undergoes a transamination to form α-aminoadipic acid. α-Aminoadipic acid undergoes a ring closure and then a reduction to form L-pipecolic acid.[7][8][9]
In the alternate pathway L-Lys cyclizes and forms the enamine, which reduces to L-pipecolic acid.
HSCoA and then malonyl-CoA react in a Claisen reaction with L-pipecolic acid to form SCoA ester which undergoes a ring closure to form 1-indolizidinone. The carbonyl on 1-indolizidinone is reduced to the hydroxyl group. The molecule is then further hydroxylated to form the final product castanospermine.[10]
