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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Preferred IUPAC name
(1S,6S,7R,8R,8aR)-Octahydroindolizine-1,6,7,8-tetrol | |
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3DMet |
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ChEBI |
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ECHA InfoCard | 100.127.469 |
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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) |
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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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Infobox references
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The castanospermine derivative celgosivir is an antiviral drug candidate currently in development for possible use in treating hepatitis C virus (HCV) infection.[6]
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]