Studies on the Chemical Modification of Monensin. III. Synthesis and Sodium Ion Transport Activity of Macrocyclic Monensylamino Acid-1,29-lactones.

• 中村 明人

• 永井 慎一

• 植田 泰誠

• 村上 啓寿

• 榊原 仁作

• 渋谷 博孝

• 北川 勲

抄録

Monensylglycine (2a) was lactonized to macrocyclic monensylglycine-1, 29-lactone (3a) by Corey's mehtod. Lactonization of monensylamino acids (2b-d) to monensylamine acid-1, 29-lactones (3b-d) was carried out by utilizing the template effect of K⁺ ion. Monobenzyl esters of dicarboxylic monensylamino acids (5e-f) also were lactonized followed by debenzylation to yield carboxylic monensylamino acid-1, 29-lactones (3e-f). Sodium ion transport activity of monensin (1) and the lactones (3) was measured in a liquid membra he and in guinea pig erythrocyte membrane. Monensylaspartic acid-1, 29-lactone (3d), monensylphenylalanine-1, 29-lactone (3c), and monensyltyrosine-1, 29-lactone (3d), having smaller Na⁺ ion transport activity than 3e, showed weak antibacterial activity, while 3e was inactive in biological tests, probably due to the lower lipophilicity.

収録刊行物

• ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ

  ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 39 (7), 1726-1730, 1991

  公益社団法人 日本薬学会

キーワード

• monensin
• monensylamino acid-1, 29-lactone
• macrolactonization
• Na<SUP>+</SUP> ion transport activity
• lipophilicity
• antibacterial activity

詳細情報

• CRID: 1390282679136952960
• NII論文ID: 110003629426
• NII書誌ID: AA00602100
• DOI: 10.1248/cpb.39.1726
• COI: 1:CAS:528:DyaK3MXmtlWqtL0%3D
• ISSN: 13475223
• ISSN: 00092363
• ISSN: http://id.crossref.org/issn/00092363
• PubMed: 1777925
• Web Site: http://www.jstage.jst.go.jp/article/cpb1958/39/7/39_7_1726/_pdf
• 本文言語コード: en
• データソース種別:
  • JaLC
  • Crossref
  • PubMed
  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可