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Oligodeoxyribonucleotide의 화학적 합성
송병수,이상직,김종대,Byong-Soo Song,Lee Sang-Jik,Jong-Dae Kim 대한화학회 1986 대한화학회지 Vol.30 No.1
"Phosphotriester Method"에 따라 모형 oligodeoxyribonuclotide로서 EcoRI인식자리를 지닌 육량체 GpApApTpTpCp를 화학적으로 합성하면서, 이 과정에 포함되는 반응물의 보호, 축합 보호기의 제거, 생성물의 정제, 정량 및 확인작업의 전반에 걸쳐 기존 방법에 대한 평가와 개선을 수행하였다. 소량체합성의 기본 단위는 이량체로 함이 효유적이며, 착합단계의 수득율은 이량체>사량체>육량체의 순으로 감소함을 알았다. UV/IR분광법 및 hplc/tlc크로마토그래피법을 이용함으로써 미량의 시료를 사용하여 Oligonucleotide를 합성함에 수반되는 정량/확인의 난점을 해결하였다. 또한 5'-OH가 노출된 nucleotide 중 전자를 과량 사용하여 반응시키고 산처리하여 탄산수소나트륨 수용액으로 세척하는 것이 양호한 방법임을 알았다. 아울러 합성에 관련된 nucleotide와 그 유도체를 분광학적 크로마토 그래피자료를 수록하였다. Along with synthesizing a model oligodeoxyribonuclotide GpApApTpTpCp which had the EcoRI recognition site according to "Phosphotriester Method", reported methods for protecting functions, condensation, deprotection, purifying products, quantification and identification were evaluated and modified. It was realized that oligomers were efficiently synthesized by elongating by dimer unit per step of the condensation and the condensation yields were decreased with increased numbers of the residues. The problems of quantification/identification involved in the oligonucleotide synthesis using small amount of the reactants were solved by employing UV/IR spectrophotometry and hplc/tlc. It was also proved that a nucleotide having the exposed 5'-OH function was well synthesized by condensing a 5'-OH nucleotide and a phosphodiester nucleotide whose molar ratio was intendedly made to be 1 : 1.2 and then detritylating followed by washing with an aqueous solution of sodium bicarbonate. Spectrophotometric and chromatographic data of the nucleotides and their derivatives concerned in this synthetic work were prepared.
Dideoxyribonucleotide의 비효소적인 방법에 의한 합성과 분리방법
이상직,송병수 嶺南大學校附設 基礎科學硏究所 1984 基礎科學硏究 Vol.4 No.-
A protected dinucleotide, 5'-O-dimethoxytritylthymidylyl-(3'→5')-3'-O-acetyl-N??-benzoyldeoxyadenosine, was synthesized by 'Phosphodiester Method' and separated by solvent extraction/recrystalization. The amino group of the base, 3'-hydroxyl group of deoxyadenosine-5'-monophosphate, and 5'-hydroxyl group of thymidine were previously protected with benzoyl, acetyl, and di-p-methoxytrityl group respectively before the condensation between the nucleotide and the nucleoside was conducted. The condensation reaction was more efficiently conducted with triisopropyl benzenesulfonyl chloride(TPS) than with dicyclohexylcarbodiimide(DCC). The dinucleotide synthesized was purified utilizing solvent systems isopropyl ether/0.5M triethylamminium bicarbonate (TEAB), ethyl ether-ethyl acetate (5:5, v/v)/0.5M TEAB, and 0.5M TEAB/CH₂CL₂-CCl₄(4:6, v/v). This method was more efficient than the ordinary diethylaminoethyl (DEAE) cellulose column chromatography.
1-Hydroxy-7-octylphenazine의 합성과 그의 항균성
金鐘大,金正煥,宋炳洙 嶺南大學校附設 基礎科學硏究所 1982 基礎科學硏究 Vol.2 No.-
1-Hydroxy-7-octylphenazine was synthesized using borontribromide by the demethoxylation of methoxy group on the phenazine ring which was prepared by the condensation of 3,4-diaminooctylbenzene and pyrogallolmonomethylether. 3,4-Diaminooctylbenzene was prepared by the reducdtion of 3-nitro-4-aminooctylbenzene and pyrogallolmonometylether by the oxidation of o-vanilline (2-hydroxy-3-methoxybenxaldehyde). Surface tension of aqueous solution of this phenazine derivative was determined by Wilhermy model surfacetensionmeter. It was found that the surface tension of 1-hydroxy-7-octylphenazine solution was lowered to about 40 dyne/cm at 10-³mol/ℓ concentration, and its CMC (critical micelle concentration) was about 1.5×10-⁴M. Antimicrobial activity of 1-hydroxy-7-octylphenazine was also observed in this study. The identification of all the reaction products and structure determination of them were performed by melting point measurement and IR/NMR Spectroscopy.