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【结 构 式】 
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【分子编号】56832 【品名】(2S)-2-{[4-({[(6R)-2-amino-4-oxo-1,4,5,6,7,8-hexahydro-6-pteridinyl]methyl}amino)benzoyl]amino}pentanedioic acid 【CA登记号】 |
【 分 子 式 】C19H23N7O6 【 分 子 量 】445.4352 【元素组成】C 51.23% H 5.2% N 22.01% O 21.55% |
合成路线1
该中间体在本合成路线中的序号：(VIIb),(XXIII)In an alternative enzymatic synthesis, exposure of the diastereoisomeric (6R,S)-tetrahydrofolates (VIIa-b), with a recombinant enzymatic domain as the source of 10-formyltetrahydrofolate synthetase activity, led to the diastereoselective formylation the (6S) tetrahydrofolate at the 10-N (XXIV), while leaving unchanged the unnatural (6R) isomer (XXIII). The chiral 10-formyl tetrahydrofolate (XXIV) was subsequently isomerized to (6S)-5-formyltetrahydrofolate either under acidic conditions, via formation of the intermediate 5,10-methenyl derivative (III) (22), or in the presence of a source of cyclohydrolase activity.
| 【1】 Pelletier, J.N.; McKenzie, R.E.; Methenyltetrahydrofolate cyclohydrolase catalyzes the synthesis of (6S)-5-formyltetrahydrofolate. Bioorg Chem 1996, 24, 3, 220. |
| 【2】 Schlingmann, G.; Rosenfeld, S.A. (Wyeth); Process for the preparation of optically pure diastereoisomers of tetrahydrofolate cpds.. EP 0432441 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VIIa) | 56817 | (2S)-2-{[4-({[(6S)-2-amino-4-oxo-1,4,5,6,7,8-hexahydro-6-pteridinyl]methyl}amino)benzoyl]amino}pentanedioic acid | C19H23N7O6 | 详情 | 详情 | |
| (VIIb),(XXIII) | 56832 | (2S)-2-{[4-({[(6R)-2-amino-4-oxo-1,4,5,6,7,8-hexahydro-6-pteridinyl]methyl}amino)benzoyl]amino}pentanedioic acid | C19H23N7O6 | 详情 | 详情 | |
| (III) | 56814 | (6aR)-3-amino-8-[4-({[(1S)-1,3-dicarboxypropyl]amino}carbonyl)phenyl]-1-oxo-1H,4H,5H,6H,6aH,7H,8H-imidazo[1,5-f]pteridin-10-ium | C20H22N7O6 | 详情 | 详情 | |
| (XXIV) | 56833 | (2S)-2-({4-[{[(6R)-2-amino-4-oxo-1,4,5,6,7,8-hexahydro-6-pteridinyl]methyl}(formyl)amino]benzoyl}amino)pentanedioic acid | C20H23N7O7 | 详情 | 详情 |