Adenine → Vidarabine

HRID 1072405

反応式

HRID 1072405 の反応式
[N:1]1[C:9]([NH2:10])=[C:8]2[C:4]([N:5]=[CH:6][NH:7]2)=[N:3][CH:2]=1.C1C(=O)NC(=O)N([C@@H:19]2[O:23][C@H:22]([CH2:24][OH:25])[C@@H:21]([OH:26])[C@@H:20]2[OH:27])C=1>P([O-])([O-])([O-])=O.O>[CH:2]1[N:3]=[C:4]2[N:5]([C@@H:19]3[O:23][C@H:22]([CH2:24][OH:25])[C@@H:21]([OH:26])[C@@H:20]3[OH:27])[CH:6]=[N:7][C:8]2=[C:9]([NH2:10])[N:1]=1

参加物

5

反応物 2

HCID 190AdenineHCID 18323Uracil Arabinoside

生成物 1

HCID 21704Vidarabine収率 51.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1061Phosphate溶媒2 回

反応条件

温度
60 °C

実験手順

50 kg of wet cell paste obtained by fermenting E. aerogenes were resuspended in approximately 200 liters of 30 mM phosphate buffer at pH 7 and mixed with 800 liters of phosphate buffer in which had been dissolved at elevated temperature 5.4 kg of adenine (final concentration 40 mM) and 8.9 kg of Ara-U (final concentration 40 mM). The mixture was maintained at 60° C., with agitation, for 20 hours, diluted to approximately 3000 liters with hot H2O and subjected to diafiltration on a membrane, collecting approximately 5000 liters of ultrafiltrate. The bioconversion yield determined by RP-HPLC was approximately 55%. The residue containing the cell paste is used for a subsequent reaction. The ultrafiltrate was concentrated to approximately 1000 liters and cooled to collect the precipitate constituted by Ara-A contaminated with non-reacted adenine (approximately 30 g of adenine per 100 g of Ara-A). 5 kg of Ara-A (total yield approximately 46%) with a degree of purity higher than 99.5% were finally obtained after crystallisation with H2O.

後処理

  1. custom50 kg of wet cell paste obtained
  2. customcollecting approximately 5000 liters of ultrafiltrate
  3. customThe bioconversion yield
  4. additionThe residue containing the cell paste
  5. customis used for a subsequent reaction
  6. concentrationThe ultrafiltrate was concentrated to approximately 1000 liters
  7. temperaturecooled
  8. customto collect the precipitate

出典と根拠

ORDレコード
ord-bcf14c3074254fa98e39459dfebc3b76
出典データセット
uspto-grants-2005_06
特許番号
US06911341B2

関連ノート

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