2007 Fiscal Year Final Research Report Summary
Synthesized cyclic nucleosides mid oligo library by catalyst
| Project/Area Number |
18550093
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Synthetic chemistry
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| Research Institution | Osaka University |
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Principal Investigator |
ZHOU Da-Yang Osaka University, The Institute of Scientific and Industrial Research, Assistant Professor (00324848)
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| Co-Investigator(Kenkyū-buntansha) |
NAKATANI Kazuhiko Osaka University, he Institute of Scientific and Industrial Research, Professor (70237303)
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| Project Period (FY) |
2006 – 2007
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| Keywords | modified nucleoside / transition metal catalyst / cyclic carbonvlation / carbon monoxide |
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| Research Abstract |
Novel modified nucleoside is important inbiochemistry and nano materials. It is much interesting in synthesized cyclic nucleoside to give new type nucleosides and their oligo library which can be used to bioactivity materials and nano materials. We use 5-iododoxycytidine and 5-iododeoxyuridine as start substrates which react with phenylacetylene to give phenylacetylene modified nucleoside by used Sonogashira reaction in high yield. The cyclic carbonylation of phenylacetyl modified nucleoside was carried out under carbon monoxide by using rhodium carbonyl catalyst, the result many complex mixture were obtained. We discuss the pressure of carbon monoxide, reaction temperature. The cyclic product was determinded by GC, but can not be separated. It is probably cause that hydroxy group can inhibit activity of catalyst. In order to solve this problem hydroxy group was protected by tert-butyldimethyisdyl group but not any effect be observed. In other band, it is indicating that base which in nucleoside may be coordinate to transition metal of catalyst and interrupt access of substrate to catalyst In this case, must to charge the base group in nucleoside. We plan to synthesis the compound which include phenyl acetyl group directly combine to five-member sugar in stead of guanine, adenine, cytosine and thymine. We hope can selectively synthesis cyclic carbonyl nucleosides in fixture. We have synthesized novel modified DNA which bearing a bipyridine metal group. Reaction of bipyridiyl acetylene with 5- iododeoxyuridine to gived 2,2-bipyridiylacetyluridine in high yield. Next synthesised the modified DNA by DNA synthesizer. The product was purified use HPLC and analysis by MLDITOFMAS. Reaction of modified DNA which bearing a bipyridine acetyl group with copper bromide. The MLDITOFMS spectral shows vale of modified DNA include a copper ion. This result has presented in 88^<th> Spring Meeting. We will synthesised the novel DNA which bearing nano metal wire in future.
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