Transformation of adenosine into N3,3'- and N3,5'-cycloadenosines via the reactions with sulfuryl chloride and thionyl chloride.

• 菊川 清見

抄録

Reaction of adenosine with sulfuryl chloride gave two compounds, 5'-chloro-5'-deoxyadenosine 2', 3'-cyclic sulfate (I) and N₃, 3'-cycloadenosine derivative (II). I was converted into 2'-sulfate (III) and 3'-sulfate (IV) by treatment with aqueous alkali and into N₄, 3'-cyclo-4-aminoimidazole 5-carboxamidine nucleoside (V) by treatment in aqueous ethanol at an elevated temperature. 5'-Chloro-5'-deoxyadenosine (VI) derived from adenosine by reaction with thionyl chloride was readily converted into N₃, 5'-cycloadenosine chloride (VIII). VIII was transformed into N₄, 5'-cyclo-4-aminoimidazole 5-carboxamidine nucleoside (XII) via the unidentified characteristic compound (X) by reaction with diluted alkali. Characteristic changes of ultraviolet spectra of VIII were described.

収録刊行物

• ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ

  ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 25 (9), 2181-2188, 1977

  公益社団法人 日本薬学会

キーワード

• N<SUB>4</SUB>, 5'-cyclo-4-aminoimidazole 5-carboxamidine nucleoside

詳細情報

• CRID: 1390282679145425152
• NII論文ID: 110003622706
• NII書誌ID: AA00602100
• DOI: 10.1248/cpb.25.2181
• ISSN: 13475223
• ISSN: 00092363
• Web Site: http://www.jstage.jst.go.jp/article/cpb1958/25/9/25_9_2181/_pdf
• Web Site: https://search.jamas.or.jp/link/ui/1978106921
• 本文言語コード: en
• データソース種別:
  • JaLC
  • Crossref
  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可