Chemistry and Biochemistry of Cycric ADP-Ribose and Its Analogs.
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- Shute Satoshi
- Graduate School of Pharmaceutical Sciences, Hokkaido University
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- Fukuoka Masayoshi
- Graduate School of Pharmaceutical Sciences, Hokkaido University
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- Matsuda Akira
- Graduate School of Pharmaceutical Sciences, Hokkaido University
Bibliographic Information
- Other Title
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- 細胞内Ca`2+´動員を担う新しいセカンドメッセンジャー・サイクリックADP‐リボース(cADPR)及びその誘導体の化学
- サイボウ ナイ Ca2 ドウイン オ ニナウ アタラシイ セカンドメッセンジャー サイクリング ADP リボース cADPR オヨビ ソノ ユウドウタイ ノ カガク
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Abstract
Cyclic ADP-ribose (cADPR, 1) is a newly discovered general mediator involved in Ca2+ signaling. The synthesis of cADPR analogs has been extensively studied by enzymatic and chemo-enzymatic methods using ADP-ribosylcyclase, due to their biological importance. ADP-ribosylcyclase from Aplysia Californica mediates the intramolecular ribosylation of NAD+ and some modified NAD+, which are prepared chemically or enzymatically, at the N-1-position of the purine moiety to yield cADPR or the corresponding analogs. However, the analogs that can be obtained by this method are limited due to the substrate-specificity of the enzyme. We developed an efficient method for the chemical synthesis of cADPR analogs and synthesized cyclic ADP-carbocyclicribose (cADPcR, 2) and its inosine congener (3, cIDPcR) as stable mimics of cADPR, in which an oxygen atom in the ribose ring of cADPR is replaced by a methylene group. Biological activities of cADPR and its analogs were also described.
Journal
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- Journal of Synthetic Organic Chemistry, Japan
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Journal of Synthetic Organic Chemistry, Japan 58 (12), 1144-1154, 2000
The Society of Synthetic Organic Chemistry, Japan
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Keywords
Details 詳細情報について
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- CRID
- 1390282680255008128
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- NII Article ID
- 10008824393
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- NII Book ID
- AN0024521X
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- ISSN
- 18836526
- 00379980
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- NDL BIB ID
- 5593953
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- Text Lang
- ja
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- Data Source
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- JaLC
- NDL
- Crossref
- CiNii Articles
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- Abstract License Flag
- Disallowed