InChI=1S/C19H26N2O2/c1- 23- 18- 4- 2- 14(3- 5- 18) 10- 16- 12- 20- 15- 11- 19(21(16) 13- 15) 8- 6- 17(22) 7- 9- 19/h2- 5,15- 16,20H,6- 13H2,1H3/p+1/t15- ,16- /m0/s1 |
CLJPQCXDNQXJBW-HOTGVXAUSA-O |
C1[C@@H]([NH+]2C[C@@H](N1)CC23CCC(=O)CC3)CC=4C=CC(=CC4)OC |
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Outgoing
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(1S,4S)- 4- [(4- methoxyphenyl)methyl]- 2,5- diazaspiro[bicyclo[3.2.1]octane- 6,1'- cyclohexan]- 4'- one(1+)
(CHEBI:233177)
is a
tertiary ammonium ion
(CHEBI:137982)
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(1S,4S)- 4- [(4- methoxyphenyl)methyl]- 2,5- diazaspiro[bicyclo[3.2.1]octane- 6,1'- cyclohexan]- 4'- one
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UniProt
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Zhang Z, Tamura Y, Tang M, Qiao T, Sato M, Otsu Y, Sasamura S, Taniguchi M, Watanabe K, Tang Y (2021) Biosynthesis of the Immunosuppressant (-)-FR901483. Journal of the American Chemical Society 143, 132-136 (Source: SUBMITTER) [PubMed:33372776] [show Abstract] We report characterization of the biosynthetic pathway of the potent immunosuppressant (-)-FR901483 (1) through heterologous expression and enzymatic assays. The biosynthetic logic to form the azatricyclic alkaloid is consistent with those proposed in biomimetic syntheses and involves aza-spiro annulation of dityrosyl-piperazine to form a ketoaldehyde intermediate, followed by regioselective aldol condensation, stereoselective ketoreduction, and phosphorylation. A possible target of 1 is proposed based on the biosynthetic studies. |
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