3'-Azido-2',3'-dideoxyuridine 5'-monophosphate → Uridine 5'-(tetrahydrogen triphosphate), 3'-azido-2',3'-dideoxy-

HRID 2073222

反応式

HRID 2073222 の反応式
[O-:1][P:2]([O:5][P:6]([O:9][P:10]([O-:13])([O-:12])=[O:11])([O-:8])=[O:7])(=[O:4])[O-:3].P(O[CH2:19][C@H:20]1[O:24][C@@H:23]([N:25]2[CH:32]=[CH:31][C:29](=[O:30])[NH:28][C:26]2=[O:27])[CH2:22][C@@H:21]1[N:33]=[N+:34]=[N-:35])(O)(O)=O.[N-]1C=CN=C1.[O-]P(OP([O-])([O-])=O)(=O)[O-].C([NH+](CCCC)CCCC)CCC.C([NH+](CCCC)CCCC)CCC.C([NH+](CCCC)CCCC)CCC.C([NH+](CCCC)CCCC)CCC>CN(C=O)C>[P:10]([O:13][CH2:19][C@H:20]1[O:24][C@@H:23]([N:25]2[CH:32]=[CH:31][C:29](=[O:30])[NH:28][C:26]2=[O:27])[CH2:22][C@@H:21]1[N:33]=[N+:34]=[N-:35])([O:9][P:6]([O:5][P:2]([OH:1])([OH:3])=[O:4])([OH:8])=[O:7])(=[O:12])[OH:11]

参加物

6

反応物 4

HCID 1594863'-Azido-2',3'-dideoxyuridine 5'-monophosphateHCID 3386966ImidazolateHCID 3440921TriphosphateHCID 21910867Tributyl ammonium pyrophosphate

生成物 1

HCID 451665Uridine 5'-(tetrahydrogen triphosphate), 3'-azido-2',3'-dideoxy-

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

The triphosphate can be prepared according to the procedure of Hoard et al., J. Am. Chem. Soc., 87(8), 1785-1788 (1965). For example, 3'-azido-2',3'-dideoxyuridine monophosphate is activated (by making a imidazolide, according to methods known to those skilled in the art) and treated with tributyl ammonium pyrophosphate in DMF. The reaction gives primarily 3'-azido-2',3'-dideoxyuridine triphosphate, with some unreacted monophosphate and some diphosphate. Purification by anion exchange chromatography of a DEAE column is followed by isolation of CS-87 triphosphate, e.g., as the tetrasodium salt.

出典と根拠

ORDレコード
ord-f23db0f896d64f78a09450647c35ca1c
出典データセット
uspto-grants-1990_04
特許番号
US04916122

関連ノート

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