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Biomedical subjects

Kazuo Kamaike

Publications and source records attributed to Kazuo Kamaike.

11 recordsLinked to original sources
PubMed2006

Efficient synthesis of [2-15N]guanosine and 2'-deoxy[2'-15N]guanosine derivatives using N-(tert-butyldimethylsilyl)[15N]phthalimide as a 15N-labeling reagent.

Nucleophilic aromatic substitution of 9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-6-chloro-2-fluoro-9H-purine with N-(tert-butyldimethylsilyl) [15N]phthalimide in the presence of a catalytic amount of CsF at room temperature in DMF efficiently afforded the 6-chloro-2-[15N]phthalimidopurine derivative, which was subsequently converted to the [2-15N]guanosine derivative. The 2'-deoxy[2'-15N]guanosine derivative was also efficiently synthesized through a similar procedure.

Deoxyguanosine↗
PubMed2005

Design, synthesis and evaluation of oligomer conjugated MGBpolyamide-nucleoside hybrid as a novel gene expression control compound.

DNA oligomers conjugated pyrrolepolyamide (minor groove binder)-deoxyguanosine hybrid were synthesized as novel gene expression control compounds. From T(m) values and CD spectral analysis, it was found that oligomers conjugated hybrid possess high recognition ability and very high binding ability for the DNA that includes pyrrolepolyamide match site.

Circular Dichroism↗
PubMed2004

New sequential-assignment routes of nucleic acid NMR signals using a [5'-(13)C]-labeled DNA dodecamer.

NMR signal assignments for DNA oligomers have been performed by the well-established sequential assignment procedures based on NOESY and COSY. The H4'/H5'/H5'' resonance region is congested and difficult to analyze without the use of isotope-labeled DNA oligomers. Here a DNA dodecamer constructed with 2'-deoxy[5'-(13)C]ribonucleotides, 5'-d(*C*G*C*G*A*A*T*T*C*G*CG)-3' (*N = [5'-(13)C]Nucleotide), was prepared in an effort to analyze the H4'/H5'/H5'' resonance region by 2D 1H-13C HMQC-NOESY. In the C5' and H1' resonance region, weak and strong cross peaks for C5'(i)-H1'(i) and C5'(i)-H1'(i-1), respectively, were found, thus enabling the sequential assignment within this region. A similar sequential assignment route was found between C5' and H2''. Proton pair distances evaluated from the canonical B-DNA as well as A-DNA indicated that these sequential-assignment routes on a 2D 1H-13C HMQC-NOESY spectrum work for most nucleic acid stem regions.

Carbon Isotopes↗
PubMed2004

Efficient syntheses of [2-(15)N]guanosine and 2'-deoxy[2-(15)N]guanosine derivatives.

Nucleophilic substitution of 9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-6-chloro-2-fluoro-9H-purine, prepared from guanosine, with N-tert-butyldimethylsilyl[(15)N]-phthalimide in the presence of a catalytic amount of CsF at room temperature in DMF efficiently afforded the 6-chloro-2-[(15)N]phthalimidopurine derivative. Treatment of this with sodium 2-cyanoethoxide yielded the [2-(15)N]guanosine derivative. The 2'-deoxy[2-(15)N]guanosine derivative was also efficiently synthesized through a similar procedure.

Deoxyguanosine↗
PubMed2004

Design, synthesis and analysis of a pyrrolepolyamide-nucleoside hybrid.

A pyrrolepolyamide-deoxyguanosine hybrid using the 3-aminopropyl linker (GAP) was designed and synthesized on the basis of previously reported results of a pyrrolepolyamide-adenosine hybrid (Apy) and a pyrrolepolyamide-deoxyguanoside hybrid using the 3-aminopropionyl linker (GBP). An evaluation of the DNA binding sequence selectivity of GAP was performed by analysis of CD spectra and Tm values using three DNA duplexes. It was shown that GAP possessed greater binding specificity than distamycin A, netropsin, Apy and GBP.

Amines↗
PubMed2003

6-(Levulinyloxymethyl)-3-methoxy-2-nitrobenzoyl and 2-(levulinyloxymethyl)-5-methoxy-4-nitrobenzoyl groups as novel base-labile groups for 5'-hydroxy protection in solid-phase oligonucleotide synthesis.

The 6-(levulinyloxymethyl)-3-methoxy-2-nitrobenzoyl (LMMoNBz) and 2-(levulinyloxymethyl)-5-methoxy-4-nitrobenzoyl (LMMpNBz) groups were developed as novel base-labile groups for 5'-hydroxy protection in solid-phase oligonucleotide synthesis. A comparative study of the utility of LMMoNBz, LMMpNBz, and 2-(levulinyloxymethyl)-5-nitrobenzoyl (LMNBz) groups is described.

Chromatography, High Pressure Liquid↗
PubMed2003

Design, synthesis and analysis of antiviral nucleosides bearing pyrrolepolyamide binding to nucleic acid (II): N2-pyrrolepolyamidopropylguanosine.

Synthesis of guanosine bearing pyrrolepolyamide (1) and analysis of DNA interaction with 1 were carried out. Compound 1 was synthesized by condensation of 2-N-beta-alanyl-3,5-TIPDS-guanosine with 1-methyl-4-[1-methyl-4-[1-methyl-4-(formylamino)pyrrole-2-carboxamido]pyrrole-2-carboxamido]pyrrole-2-carboxylic acid which was prepared from N-methylpyrrole. To investigate the interaction between 1 and DNA in Circular Dichroism spectra and Tm values, we used distamycin A and adenosine bearing pyrrolepolyamide (Apy), which has the high sequence-selectivity of DNA, as a contrast.

Antiviral Agents↗
PubMed2003

Synthesis of oligonucleoside phosphorodithioates by the H-phosphonothioate method using bis(2,6-dimethylphenyl)phosphorochloridate as a coupling agent.

The phosphorodithioate octamer [(TpS2)7T] was efficiently synthesized using bis(2,6-dimethylphenyl)phosphorochloridate as a coupling agent by the H-phosphonothioate method, which performed the sulfurization with elemental sulfur after completion of oligonucleoside H-phosphonothioate assembly, as the standard H-phosphonate method.

Chromatography, High Pressure Liquid↗
PubMed2002

Novel base-labile protecting groups for 5'-hydroxyl protection in the synthesis of oligonucleotides.

The 6-(levulinyloxymethyl)-3-methoxy-2-nitrobenzoyl (LMM0NBz) and 2-(levulinyloxy-methyl)-5-methoxy-4-nitrobenzoyl (LMMpNBz) groups were developed as novel base-labile protection for the 5'-hydroxyl group in solid-phase oligonucleotide synthesis. A comparative study on the utility of LMMoNBz, LMMpNBz, and 2-(levulinyloxymethyl)-5-nitrobenzoyl (LMNBz) groups for the synthesis of oligodeoxyribonucleotides, and the synthesis of oligoribonucleotides using the LMMoNBz group in combination with the acid-labile 1-ethoxyethylk (EE) group to protect the 2'-hydroxyl group, are described.

Hydroxyl Radical↗
PubMedDate not supplied

Novel base-labile protecting groups for 5'-hydroxy function in solid-phase oligonucleotide synthesis.

The 6-(levulinyloxymethyl)-3-methoxy-2-nitrobenzoyl (LMMoNBz) and 2-(levulinyloxymethyl)-5-methoxy-4-nitrobenzoyl (LMMpNBz) groups were developed as novel base-labile protection for the 5'-hydroxy function in solid-phase oligonucleotide synthesis. A comparative study of the LMMoNBz, LMMpNBz and 2-(levulinyloxymethyl)-5-nitrobenzoyl (LMNBz) protecting groups for oligonucleotide synthesis proved strong feasibility for the LMMoNBz group.

Chromatography, High Pressure Liquid↗