Synthesis of Nucleosides and Related Compounds. XXXI. Resolution of 9-[c-4, t-5-Bis(hydroxymethyI)cyclopent-2-en-r-l-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(hydroxymethyI)cyclopent-2-en-r-l-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

PHA - Pharmacy

Research output: Contribution to journal › Article › peer-review

9 Citations (Scopus)

Abstract

Deamination of an anti-human immunodeficiency virus (anti-HIV) carbocyclic adenine nucleoside, 9-[c-4, t-5-bis(hydroxymethyl)cyclopent-2-en-r-l-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.

Original language	English
Pages (from-to)	1027-1029
Number of pages	3
Journal	Chemical and Pharmaceutical Bulletin
Volume	41
Issue number	6
DOIs	https://doi.org/10.1248/cpb.41.1027
Publication status	Published - 1993

Keywords

9-cyclopentenylhypoxanthine
adenosine deaminase
anti-HIV activity
carbocyclic adenine nucleoside
enzymatic resolution
high-pressure

ASJC Scopus subject areas

Chemistry(all)
Drug Discovery

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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Katagiri, N., Shiraishi, T., Toyota, A., Sato, H., Kaneko, C., & Aikawa, T. (1993). Synthesis of Nucleosides and Related Compounds. XXXI. Resolution of 9-[c-4, t-5-Bis(hydroxymethyI)cyclopent-2-en-r-l-yl]-9H-adenine [(±)-BCA] by Means of High-Pressure-Mediated Deamination with Adenosine Deaminase. Chemical and Pharmaceutical Bulletin, 41(6), 1027-1029. https://doi.org/10.1248/cpb.41.1027

Synthesis of Nucleosides and Related Compounds. XXXI. Resolution of 9-[c-4, t-5-Bis(hydroxymethyI)cyclopent-2-en-r-l-yl]-9H-adenine [(±)-BCA] by Means of High-Pressure-Mediated Deamination with Adenosine Deaminase. / Katagiri, Nobuya; Shiraishi, Takuya; Toyota, Akemi et al.

In: Chemical and Pharmaceutical Bulletin, Vol. 41, No. 6, 1993, p. 1027-1029.

Research output: Contribution to journal › Article › peer-review

Katagiri, N, Shiraishi, T, Toyota, A, Sato, H, Kaneko, C & Aikawa, T 1993, 'Synthesis of Nucleosides and Related Compounds. XXXI. Resolution of 9-[c-4, t-5-Bis(hydroxymethyI)cyclopent-2-en-r-l-yl]-9H-adenine [(±)-BCA] by Means of High-Pressure-Mediated Deamination with Adenosine Deaminase', Chemical and Pharmaceutical Bulletin, vol. 41, no. 6, pp. 1027-1029. https://doi.org/10.1248/cpb.41.1027

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abstract = "Deamination of an anti-human immunodeficiency virus (anti-HIV) carbocyclic adenine nucleoside, 9-[c-4, t-5-bis(hydroxymethyl)cyclopent-2-en-r-l-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.",

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AU - Katagiri, Nobuya

AU - Shiraishi, Takuya

AU - Toyota, Akemi

AU - Sato, Hiroshi

AU - Kaneko, Chikara

AU - Aikawa, Toyoo

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AB - Deamination of an anti-human immunodeficiency virus (anti-HIV) carbocyclic adenine nucleoside, 9-[c-4, t-5-bis(hydroxymethyl)cyclopent-2-en-r-l-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.

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

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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