Английская Википедия:Castanospermine
Castanospermine is an indolizidine alkaloid first isolated from the seeds of Castanospermum australe.[1] It is a potent inhibitor of some glucosidase enzymes[2] and has antiviral activity in vitro and in mouse models.[3]
The castanospermine derivative celgosivir is an antiviral drug candidate currently in development for possible use in treating hepatitis C virus (HCV) infection.[4]
Biosynthesis of castanospermine
L-Lys undergoes a transamination to form α-aminoadipic acid. α-aminoadipic acid undergoes a ring closure and then a reduction to form L-pipecolic acid (Figure 1).[5] In the alternate pathway (Figure 2), 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.[6]
Biosynthesis shown in figure:[7][8]
See also
References
