• 제목/요약/키워드: Guanine

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Deguanylation of Guanine Based-Nucleosides and Calf Thymus DNA Induced by Halogenated Alkanes at the Physiological Condition

  • Sherchan, Jyoti;Lee, Eung-Seok
    • Bulletin of the Korean Chemical Society
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    • 제30권12호
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    • pp.2949-2958
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    • 2009
  • Massive deguanylation of guanine based-nucleosides induced by halogenated alkanes at the physiological condition have been observed. For the study of deguanylation effects by the different substituents and/or functionality in halogenated alkanes, diverse kinds of halogenated alkanes were incubated with guanine based-nucleosides (ddG, dG and guanosine) for 48 h at the physiological condition (pH 7.4, 37$^{\circ}C$), which were analyzed by HPLC and further confirmed by LC-MS. Among the sixteen different halogenated alkanes, we observed massive deguanylation of nucleosides by 2-bromo-2-methylpropane, 2,3-dibromopropene, 2-bromopropane, bromoethane and 2-iodopropane. The order of deguanylation rate was highest in 2-bromo-2-methylpropane followed by 2,3-dibromopropene, 2-bromopropane, bromoethane and 2-iodopropane. In addition, time and dose response relationship of deguanylation in guanine basednucleosides induced by 2-bromo-2-methylpropane, 2,3-dibromopropene, 2-bromopropane, bromoethane and 2-iodopropane at the physiological condition were investigated. Deguanylation of calf thymus DNA induced by halogenated alkanes was also investigated. These results suggest that the toxic effect of certain halogenated alkanes might be from the depurination of nucleosides.

Development of New Protecting Groups for Guanine Residue in Oligodeoxyribonucleotide Synthesis

  • Byung Jo Moon;Kyung Lan Huh
    • Bulletin of the Korean Chemical Society
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    • 제12권2호
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    • pp.196-199
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    • 1991
  • Attempts were made to develop new protecting groups for 1,6-lactam function of 2-N-acyl guanine in oligodeoxyribonucleotide synthesis. Several acyl groups, aryl groups, and carbamoyl groups were tested. Dimethylcarbamoyl and phenylacetyl groups are shown to be a good combination for guanine residue. 6-O-Di-methylcarbamoyl-2-N-pheylacetyl-2'-deoxy guanosine have been successfully used in the synthesis of d[AAGCTT], which is Hind Ⅲ recognition sequence.

Brevibacterium ammoniagenes 의 아데닌-구아닌 복영양요구주에(複營養要求株)에 의한 5'-크산틸산(酸)의 축적(蓄積) (Accumulation of Xanthosine-5'-monophosphate by Adenine-Guanine Double Auxotroph of Brevibacterium ammoniagenes)

  • 공운영;우형구;손충홍;배종찬;유주현
    • 한국식품과학회지
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    • 제13권2호
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    • pp.121-126
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    • 1981
  • Brevibacterium ammoniagenes ATCC 6872를 변이하여 얻은 adenine-guanine 및 $\beta$-alanine 영양요구성(營養要求性)이고 5'-XMP를 다량 생산하는 변이주 D-1550-40을 사용하여 발효배지성분(醱酵培地成分)의 최고농도(最高濃度)와 각 성분간의 상호작용효과(相互作用效果)를 검토하였다. 5'-XMP 축적(蓄積)에 필요한 adenine 및 guanine의 최적(最適) 농도(濃度)는 각각 75mg/l이었으나 생육(生育)에 대한 최적농도(最適濃度)는 이 보다 높은 100mg/ml이었고 그 이상의-농도에서는 5'-XMP 축적에 심한 저해를 초래하였다. 이러한 현상은 biotin을 $100{\mu}g/l$ 이상 첨가하거나 casamino acid를 0.3% 이상 첨가함으로서 배제할 수 있었다. 5'-lMP 발효의 경우와 마찬가지로 무기인산염(無機燐酸鹽)과 마그네슘은 5'-XMP 축적에도 $1.0{\sim}1.5%$1.5%가 적당(適當)하였다. $MnSO_4$의 농도가 $0{\sim}5mg/l$의 범위안에서 증가함에 따라 균증식과 5'-XMP의 축적은 촉진되었으나 그 이상의 농도에서는 변화가 없었고 정상상태를 나타내었다. Adenine과 guanine 각 100 mg/l, $MnSO_4\{cdot}7H_2O5mg/l 및 biotin $100{\mu}g/lg$가 함유된 발효배지에서 배양한 결과 4일후 60.5mg/ml의 5'-XMP가 측적되었으며, 5'-XMP의 생성활성(生成活性)은 균체량(菌體量)에 비례하여 배양 2일 내지 3일에서 가장 높았다.

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Pseudomonas synxantha A3가 생산하는 세포외 Guanine Deaminase의 성질 (The Properties of Extracellular Guanine Deaminase from Pseudomonas synxantha A3)

  • 전홍기;박정혜;이성태
    • 한국미생물·생명공학회지
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    • 제14권6호
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    • pp.441-446
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    • 1986
  • Pseudomonas synxantha A3가 생산하는 세포외 guanine deaminase의 몇가지 성질을 검토하였다. 본 효소의 안정 pH는 6.5-7.5 부근이었으며, 열안정성을 검토하기 위하여 각 온도에서 10분간 처리하였을 때 4$0^{\circ}C$까지 안정하였고 그 이상의 온도에서는 서서히 실활되었다. 또한 pH 8.0의 0.2M potassium phosphate 완충액에 본 효소를 보관하였을 때 실온에서 30일간 안정하였고 alcohol 및 acetone은 본 효소의 안정화에 효과가 없었다. 효소활성을 위한 최적온도 및 pH는 각각 5$0^{\circ}C$와 pH 7-8 부근이었다. 본 효소는 1mM의 Hg$^{++}$, Ag$^+$, Li$^+$에 의해 각각 50%이상 저해되었으며, 0.1mM의 Ag$^+$에 의해서도50%이상 저해되었다. Li$^+$에 의해 저해된 본 효소에 EDTA를 가하였을 때 효소의 활성회복에 효과가 있었다. 본 효소의 활성은 1mM의 pentachlorophenol에 의해 50%, p-CMB에 의해 40%정도 저해되었다. p-CMB에 의해 저해된 본 효소에 thiol compound를 가하였을 때에는, 사용된 시약 중 glutathione이 본 효소의 활성회복에 효과적인 것으로 나타났다.

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Aspen Chromatography 전산모사와 HPLC를 이용한 구아닌 시토신의 분리특성연구 (Separation Study of Cytosine and Guanine by HPLC and Aspen Chromatography)

  • 박문배;김인호
    • Korean Chemical Engineering Research
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    • 제48권1호
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    • pp.88-92
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    • 2010
  • DNA 구조를 밝히기 위해 의학, 약학 그리고 생명과학분야 등에서 활발한연구가 이루어지고 있다. 그 중 DNA의 염기쌍은 생명체의 정보 전달에 매우 중요한 역할을 하므로 염기쌍의 집중적인 분석이 필요하다. 그래서 DNA의 염기쌍 중 하나인 구아닌과 시토신을 선택하여 분석 실험을 하였다. 구아닌과 시토신의 분석은 Aspen chromatography 전산모사와 HPLC(High Performance Liquid Chromatography) 실험을 통하여 이루어졌다. Aspen Chromatography(ver. 2006 Aspen Tech. U.S.A)로 시료농도, 이동상 유속 그리고 이론단수를 변화시켜 전산모사하였다. HPLC 실험은 $C_{18}$ HPLC column 칼럼과 이동상 water/methanol/acetic acid 혼합액(90/10/0.1)을 이용하여 시료의 주입 농도와 이동상 속도를 변화시켰고 구아닌과 시토신의 크로마토그램의 분리도와 이론단수를 비교하였다. 실험과 전산모사 크로마토그래피 결과가 비교적 일치하였다.

Synthesis, Characterization and in Vitro Identification of $N^7-Guanine$ Adduct of 2-Bromopropane

  • Zhao, Long-Xuan;Kim, Eun-Kyung;Lim, Hyun-Tae;Moon, Yoon-Soo;Kim, Nam-Hee;Kim, Tae-Hyung;Choi, Heesung;Chae, Whigun;Jeong, Tae-Cheon;Lee, Eung-Seok
    • Archives of Pharmacal Research
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    • 제25권1호
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    • pp.39-44
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    • 2002
  • Recently, we have reported that 2-bromopropane might have an immunotoxic potential in rats when exposed for 28 days. In the present studies, the possibility of 2i-deoxyguanosine abduct formation by 2- bromopropane was investigated in vitro to elucidate molecular mechanism of 2-bromopropane-induced immunosuppression. $N^7-Guanine adduct$ of 2'-bromopropane (i.e., $N^7-isopropyl$ guanine) was chemically synthesized and structurally characterized by analysis of UV,$^1H-NMR,{\;}^{13}C-NMR$, COSY and fast atom bombardment mass spectrometry to use as a reference material. Incubation of 2'-deoxyguanosine with an excess amount of 2-bromopropane in PBS buffer solution, pH 7.4, at $37^{\circ}C$ for 16 h, followed by a thermal hydrolysis, produced a detectable amount of $N^7-isopropyl$ guanine by an HPLC and UV analysis. The present results suggest that 2-bromopropane might form a DNA adduct in $N^7-position$ of 2'-deoxyguanosine at 3 Physiological condition.

An anomalous dissociation of protonated cluster ions of DNA guanine-cytosine base-pair

  • Seong, Yeon-Mi;Han, Sang-Yun;Jo, Sung-Chan;Oh, Han-Bin
    • Mass Spectrometry Letters
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    • 제2권3호
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    • pp.73-75
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    • 2011
  • In the collisionally-activated dissociation of the proton-bound cluster ions of DNA base guanine (G) and cytosine (C), $G{\bullet}{\bullet}H^+{\bullet}{\bullet}C$, the abundance of [$CH^+$] ions was found to be higher than that of [$GH^+$] despite the fact that G has a higher proton affinity than C. This unexpected observation seems to demonstrate another example that the simple kinetic method scheme does not work. We suggest that a kinetic factor or detailed dynamics governing the proton transfer and dissociation should be carefully considered in the applications of the kinetic method to the proton affinity measurements.

Chemical Modification of Transducin with Dansyl Chloride Hinders Its Binding to Light-activated Rhodopsin

  • Kosoy, Ana;Moller, Carolina;Perdomo, Deisy;Bubis, Jose
    • BMB Reports
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    • 제37권2호
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    • pp.260-267
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    • 2004
  • Transducin (T), the heterotrimeric guanine nucleotide binding protein in rod outer segments, serves as an intermediary between the receptor protein, rhodopsin, and the effector protein, cGMP phosphodiesterase. Labeling of T with dansyl chloride (DnsCl) inhibited its light-dependent guanine nucleotide binding activity. Conversely, DnsCl had no effect on the functionality of rhodopsin. Approximately 2-3 mol of DnsCl were incorporated per mole of T. Since fluoroaluminate was capable of activating DnsCl-modified T, this lysine-specific labeling compound did not affect the guanine nucleotide-binding pocket of T. However, the labeling of T with DnsCl hindered its binding to photoexcited rhodopsin, as shown by sedimentation experiments. Additionally, rhodopsin completely protected against the DnsCl inactivation of T. These results demonstrated the existence of functional lysines on T that are located in the proximity of the interaction site with the photoreceptor protein.