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Nucleosides and Nucleotides. 192. Toward the Total Synthesis of Cyclic ADP-Carbocyclic-Ribose. Formation of the Intramolecular Pyrophosphate Linkage by a Conformation-Restriction Strategy in a Syn-form Using a Halogen Substitution at the 8-Position of the Adenine Ring
| Title: | Nucleosides and Nucleotides. 192. Toward the Total Synthesis of Cyclic ADP-Carbocyclic-Ribose. Formation of the Intramolecular Pyrophosphate Linkage by a Conformation-Restriction Strategy in a Syn-form Using a Halogen Substitution at the 8-Position of the Adenine Ring |
| Authors: | Sumita, Yuji Browse this author | | Shirato, Michiyo Browse this author | | Ueno, Yoshihito Browse this author | | Matsuda, Akira Browse this author | | Shuto, Satoshi Browse this author |
| Issue Date: | 2000 |
| Publisher: | Taylor & Francis |
| Journal Title: | Nucleosides, Nucleotides and Nucleic Acids |
| Volume: | 19 |
| Issue: | 1-2 |
| Start Page: | 175 |
| End Page: | 187 |
| Publisher DOI: | 10.1080/15257770008033002 |
| PMID: | 10772708 |
| Abstract: | The synthesis of cyclic ADP-carbocyclic-ribose (2), as a stable mimic for cyclic ADP-ribose, was investigated. Construction of the 18-membered backbone structure was successfully achieved by condensation of the two phosphate groups of 19, possibly due to restriction of the conformation of the substrate in a syn-form using an 8-chloro substituent at the adenine moiety. SN2 reactions between an optically active carbocyclic unit 8, which was constructed by a previously developed method, and 8-bromo-N6-trichloroacetyl-2’,3’-0-isopropylideneadenosine 9c gave N-1-carbocyclic derivative, which was deprotected to give 5’,5”-diol derivatives 18. When 18 was treated with POCl3 in PO(OEt)3, the bromo group at the 8-position was replaced to give N-1-carbocyclic-8-chloroadenosine 5’,5”-diphosphate derivative 19 in 43% yield. Treatment of 19 with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride gave the desired intramolecular condensation product 20 in 10% yield. This is the first chemical construction of the 18-membered backbone structure containing an intramolecular pyrophosphate linkage of a cADPR-related compound with an adenine base. |
| Rights: | This is an electronic version of an article published in Nucleosides, Nucleotides & Nucleic Acids, 19(1-2), 175-187, 2000. Nucleosides, Nucleotides & Nucleic Acids is available online at: http://www.informaworld.com/openurl?genre=article&issn=15257770&volume=19&issue=1-2&spage=175 |
| Type: | article (author version) |
| URI: | http://hdl.handle.net/2115/46971 |
| Appears in Collections: | 薬学研究院 (Faculty of Pharmaceutical Sciences) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)
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Submitter: 松田 彰
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