Synthesis of Nucleosides and Related Compounds. XXXI. Resolution of 9-[c-4, t-5-Bis(hydroxymethyl)cyclopent-2-en-r-1-yl]-9H-adenine [(±)-BCA] by Means of High-Pressure-Mediated Deamination with Adenosine Deaminase

Nobuya KATAGIRI; Takuya SHIRAISHI; Akemi TOYOTA; Hiroshi SATO; Chikara KANEKO; Toyoo AIKAWA

doi:10.1248/cpb.41.1027

Synthesis of Nucleosides and Related Compounds. XXXI. Resolution of 9-[c-4, t-5-Bis(hydroxymethyl)cyclopent-2-en-r-1-yl]-9H-adenine [(±)-BCA] by Means of High-Pressure-Mediated Deamination with Adenosine Deaminase

片桐信弥, 白石拓也, 豊田朱見, 佐藤弘, 金子主税, 相川豊夫

著者情報

キーワード: adenosine deaminase, high-pressure, enzymatic resolution, anti-HIV activity, carbocyclic adenine nucleoside, 9-cyclopentenylhypoxanthine

ジャーナルフリー

1993 年 41 巻 6 号 p. 1027-1029

DOI https://doi.org/10.1248/cpb.41.1027

詳細

抄録

Deamination of an anti-human immunodeficiency virus (anti-HIV) carbocyclic adenine nucleoside, 9-[c-4, t-5-bis(hydroxymethyl)cyclopent-2-en-r-1-yl]-9H-adenine (BCA) by adenosine deaminase under a variety of pressures (1 bar-6 kbar) was investigated. It was found that, while (+)-BCA was practically unaffected, the deamination of (-)-BCA was remarkably enhanced under 4 kbar to give the corresponding (-)-hypoxanthine derivative [(-)-BCH] in nearly 100% ee.

責任著者(Corresponding author)

J-STAGEへの登録はこちら（無料）