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Nucleic acids symposium series (2004)最新文献

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Synthesis of deuterated benzyladenine and its application as a surrogate. 氘化苄基腺嘌呤的合成及其替代应用。
Pub Date : 2009-01-01 DOI: 10.1093/nass/nrp053
Nkaelang Modutlwa, Hiroyuki Tada, Yoshiki Sugahara, Koichi Shiraki, Nobuyuki Hara, Yoshihiro Deyashiki, Takayuki Ando, Tomohiro Maegawa, Yasunari Monguchi, Hironao Sajiki

Palladium on carbon-ethylenediamine complex [Pd/C(en)] catalyzed deuteration of N(6)-benzyladenine-d(5), which is a plant growth regulator, to introduce 5 deuterium atoms, while use of Pd/C as a catalyst led to a complete removal of N(6)-benzyl group. The corresponding deuterated N(6)-benzyladenine was successfully used as a surrogate compound for the quantitative analysis of residual benzyladenine in crops using LC/MS/MS.

钯在碳-乙二胺配合物[Pd/C(en)]上催化植物生长调节剂N(6)-苄基ladenine-d(5)的氘化,引入5个氘原子,而Pd/C作为催化剂可使N(6)-苄基完全去除。将相应的氘化N(6)-苄基腺苷作为替代物,采用LC/MS/MS技术对作物中残留的苄基腺苷进行了定量分析。
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引用次数: 7
Release of DNA binary complexes from the ternary complexes by carboxymethyl poly(L-histidine). 羧甲基聚l -组氨酸从三元配合物中释放DNA二元配合物。
Pub Date : 2009-01-01 DOI: 10.1093/nass/nrp127
Shoichiro Asayama, Miyuki Sudo, Hiroyoshi Kawakami

The DNA ternary complexes with carboxymethyl poly(L-histidine) (CM-PLH) and poly(ethylenimine) (PEI) have released the DNA binary complexes with PEI by the protonation of CM-PLH at endosomal/lysosomal pH. The dissociation of the CM-PLH from the CM-PLH/PEI/DNA ternary complexes is proved by the fluorescence resonance energy transfer (FRET) analysis between the CM-PLH and PEI. The resulting PEI/DNA binary complexes easily released DNA, as compared with the CM-PLH/PEI/DNA ternary complexes, which was examined by competitive exchange with dextran sulfate. The release of the DNA binary complexes from the ternary complexes is promising mechanism for higher transfection activity by the CM-PLH/PEI/DNA ternary complexes.

与羧甲基聚l -组氨酸(CM-PLH)和聚亚胺(PEI)的DNA三元配合物通过CM-PLH在内体/溶酶体ph处的质子化作用释放出与PEI的DNA二元配合物。CM-PLH与PEI之间的荧光共振能量转移(FRET)分析证实了CM-PLH与CM-PLH/PEI/DNA三元配合物的解离作用。与CM-PLH/PEI/DNA三元配合物相比,得到的PEI/DNA二元配合物更容易释放DNA,并与硫酸葡聚糖竞争交换。从三元配合物中释放DNA二元配合物是CM-PLH/PEI/DNA三元配合物提高转染活性的有希望的机制。
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引用次数: 1
Reaction of the 4'-benzenesulfonyl derivatives of thymidine with organosilicon and organoaluminum reagents. 胸腺嘧啶的4′-苯磺酰衍生物与有机硅和有机铝试剂的反应。
Pub Date : 2009-01-01 DOI: 10.1093/nass/nrp001
Hisashi Shimada, Satoshi Kikuchi, Saori Okuda, Kazuhiro Haraguchi, Hiromichi Tanaka

With an aim to develop a new approach to synthesize 4'-substituted nucleosides, reactions of thymidine derivatives having a benzenesulfonyl leaving group at the 4'-position with organosilicon and organoaluminum reagents were investigated. Two substrates 4alpha (alpha-L-isomer) and 4 beta (beta-D-isomer) were prepared for this purpose. Although reaction of 4alpha with organosilicon reagents gave preferentially the 4'-substituted (allyl and N(3)) beta-D-nucleoside, its reaction with AlMe(3) gave the 4'-methyl-alpha-L-thymidine as the major product. On the other hand, the substrate 4beta, upon reacting with AlMe(3), furnished the desired 4'-methylthymidine exclusively in high yield.

为了探索合成4′取代核苷的新方法,研究了4′位置有苯磺酰基离去基的胸腺苷衍生物与有机硅和有机铝试剂的反应。为此制备了两种底物4α (α - l -异构体)和4 β (β - d -异构体)。虽然4 α与有机硅试剂反应优先生成4′-取代(烯丙基和N(3)) β - d -核苷,但与AlMe(3)反应生成4′-甲基- l-胸腺嘧啶作为主要产物。另一方面,底物4 β与AlMe(3)反应后,以高收率提供所需的4'-甲基胸腺嘧啶。
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引用次数: 0
Stereocontrolled synthesis of oligodeoxyribonucleoside boranophosphates via stereodefined H-phosphonate intermediates. 通过立体定义的h -膦酸盐中间体立体控制合成硼磷酸寡脱氧核糖核苷。
Pub Date : 2009-01-01 DOI: 10.1093/nass/nrp005
Naoki Iwamoto, Natsuhisa Oka, Takeshi Wada
P-Stereodefined oligodeoxyribonucleoside boranophosphates (PB-ODNs) were successfully synthesized by the conversion of diastereopure H-phosphonate intermediates. Thermal denaturation studies clearly showed that the duplex stability of PB-ODNs with the complementary DNA and RNA depends on the stereochemistry of the boranophosphate linkages.
通过非对纯h -膦酸盐中间体的转化,成功合成了p -立体定向的硼磷酸寡脱氧核糖核苷(PB-ODNs)。热变性研究清楚地表明,PB-ODNs与互补DNA和RNA的双相稳定性取决于硼磷酸盐键的立体化学性质。
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引用次数: 4
Metal ion binding of modified pyrimidine-base pairs in DNA duplexes. DNA双链中修饰嘧啶碱基对的金属离子结合。
Pub Date : 2009-01-01 DOI: 10.1093/nass/nrp009
Akira Ono, Kenji Iwamoto, Kumiko Sugiyama, Itaru Okamoto

We report the synthesis and metal ion-binding properties of DNA duplexes containing 5-substituted uracil ((X)U) pairs, such as 5-bromouracil, 5-fluorouracil and 5-cyanouracil pairs. Thermal denaturation studies of these modified DNA duplexes revealed that the DNA duplexes were stabilized in the presence of Hg(II) ions in acidic and neutral solutions. On the other hand, the duplexes were stabilized in the presence of Hg(II) and Ag(I) ions. These results indicated that (X)U-Hg(II)-(X)U complex was formed in the acidic and neutral solutions, then, in the basic solutions (X)U-Ag(I)-(X)U complex as well as the (X)U-Hg(II)-(X)U complex were formed. ESI-TOF MS analysis also indicated formation of the metal ion-DNA complexes.

我们报道了含有5-取代尿嘧啶((X)U)对的DNA双链的合成和金属离子结合性质,如5-溴脲嘧啶、5-氟尿嘧啶和5-氰脲嘧啶对。对这些修饰的DNA双链的热变性研究表明,DNA双链在酸性和中性溶液中在Hg(II)离子存在下是稳定的。另一方面,双相化合物在Hg(II)和Ag(I)离子存在下稳定。结果表明,(X)U- hg (II)-(X)U配合物首先在酸性溶液和中性溶液中形成,然后在碱性溶液中形成(X)U- ag (I)-(X)U配合物和(X)U- hg (II)-(X)U配合物。ESI-TOF MS分析也显示了金属离子- dna络合物的形成。
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引用次数: 0
Introduction of 8-methyladenosine into 2', 5'-oligoadenylate (2-5A) 2'-terminus induces dramatic shift in binding site of RNase L. 将8-甲基腺苷引入2',5'-寡聚腺苷酸(2- 5a) 2'端可引起RNase L结合位点的剧烈移位。
Pub Date : 2009-01-01 DOI: 10.1093/nass/nrp062
Kumi Nagaoka, Seiya Kito, Yoshiaki Kitamura, Yoshihito Ueno, Yukio Kitade

The 2',5'-oligoadenylate (2-5A) system is an interferon (IFN)-regulated RNA decay pathway that provides innate immunity against viral infections. The biological action of the 2-5A system is mediated by RNase L, an endoribonuclease that becomes enzymatically active after binding to 2-5A. It has been reported that the 5'-phosphoryl group of 2-5A is required for RNase L activation. However, we have found that 5'-O-dephosphorylated 2-5A tetramer analogs with 8-methyladenosine at the 2'-terminus were more effective as an activator of RNase L than the parent 2-5A (p5'A2'p5'A2'p5'A2'p5'A2'). Introduction of 8-methyladenosine is thought to induce a dramatic shift in the binding site of RNase L.

2',5'-寡聚腺苷酸(2- 5a)系统是干扰素(IFN)调控的RNA衰变途径,提供抗病毒感染的先天免疫。2-5A系统的生物学作用是由核糖核酸内切酶RNase L介导的,RNase L与2-5A结合后具有酶活性。据报道,2-5A的5'-磷酸化基团是RNase L激活所必需的。然而,我们发现在2'端具有8-甲基腺苷的5'- o -去磷酸化2- 5a四聚体类似物作为RNase L的激活剂比亲本2- 5a (p5'A2'p5'A2'p5'A2'p5'A2' p5' a2 ')更有效。8-甲基腺苷的引入被认为会引起RNase L结合位点的剧烈变化。
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引用次数: 1
Unnatural imidazopyridopyrimidine:naphthyridine base pairs: selective incorporation and extension reaction by DNA polymerases. 非天然咪唑吡啶嘧啶:萘啶碱基对:DNA聚合酶的选择性掺入和延伸反应。
Pub Date : 2009-01-01 DOI: 10.1093/nass/nrp063
Noriaki Minakawa, Shintaro Ogata, Mayumi Takahashi, Akira Matsuda

We describe herein the results of (i) enzymatic recognition for imidazopyridopyrimidine (Im):naphthyridine (Na) base pairs and (ii) further primer extension reactions after the Im:Na base pairs by DNA polymerases. Among the base pairs examined, ImN(O):NaO(N) base pair was rather selectively recognized by Klenow fragment exo(-) [F(exo(-))]as complementary base. However, this DNA polymerase did not catalyze primer extension reactions after the ImN(O):NaO(N) base pair. Therefore, we carried out a screening of DNA polymerases to promote the primer extension reaction as well as to improve the selectivity of base pair recognition. As a result, a family B DNA polymerase, especially Deep Vent (exo(-)), seemed most promising for this purpose.

我们在这里描述了(i)酶对咪唑吡啶(Im):萘啶(Na)碱基对的识别结果,以及(ii) DNA聚合酶在Im:Na碱基对之后进一步的引物延伸反应。在检测的碱基对中,ImN(O):NaO(N)碱基对被Klenow片段exo(-) [F(exo(-))]选择性识别为互补碱基对。然而,该DNA聚合酶在ImN(O):NaO(N)碱基对后不催化引物延伸反应。因此,我们对DNA聚合酶进行筛选,以促进引物延伸反应,提高碱基对识别的选择性。因此,B家族DNA聚合酶,特别是深喷口(exo(-)),似乎最有希望实现这一目的。
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引用次数: 1
Evaluation of base recognition abilities of 2'-deoxynucleoside N-oxide derivatives by polymerase reactions. 用聚合酶反应评价2'-脱氧核苷n -氧化物衍生物的碱基识别能力。
Pub Date : 2009-01-01 DOI: 10.1093/nass/nrp064
Hirosuke Tsunoda, Akihiro Ohkubo, Kohji Seio, Mitsuo Sekine
The main products obtained by oxidation of cytosine and adenine bases with hydrogen peroxide are cytosine and adenine N-oxide derivatives. There is a possibility that these N-oxide derivatives are mutagenic in genomic DNA like 8-oxoguanine or thymine glycol. Although the chemical synthesis and properties of 2'-deoxynucleoside N-oxide derivatives have been well established, little has been reported about the chemical and biochemical behavior of oligodeoxynucleotides (ODNs) containing these modified 2'-deoxynucleoside. In this study, we examined their base recognition ability by DNA polymerase reactions. It was found that these modified derivatives were incorporated into the 3'-terminal site of an ODN by DNA polymerase selecting accurately the complementary G or T base on a template ODN. In the incorporation reaction using template ODNs containing 2'-deoxynucleoside N-oxide bases, their N-oxide bases were selectively recognized by the complementary 5'-triphosphate (dGTP or dTTP).
双氧水氧化胞嘧啶和腺嘌呤碱得到的主要产物是胞嘧啶和腺嘌呤n -氧化物衍生物。这些n -氧化物衍生物有可能像8-氧鸟嘌呤或胸腺嘧啶乙二醇一样在基因组DNA中具有诱变作用。虽然2'-脱氧核苷n -氧化物衍生物的化学合成和性质已经得到了很好的证实,但关于含有这些修饰的2'-脱氧核苷的寡脱氧核苷酸(ODNs)的化学和生化行为的报道很少。在本研究中,我们通过DNA聚合酶反应检测了它们的碱基识别能力。研究发现,这些修饰的衍生物通过DNA聚合酶精确地选择模板ODN上互补的G或T碱基,被整合到ODN的3'端。在含有2'-脱氧核苷n -氧化物碱基的模板odn掺入反应中,它们的n -氧化物碱基被互补的5'-三磷酸(dGTP或dTTP)选择性识别。
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引用次数: 0
Duplex formation of multiple pyrene-modified RNAs. 多个芘修饰rna的双工形成。
Pub Date : 2009-01-01 DOI: 10.1093/nass/nrp067
Minoru Fukuda, Mitsunobu Nakamura, Tadao Takada, Kazushige Yamana

We synthesized multiple pyrene-modified RNA sequences having two kinds of consecutive sequences, U(Py)U(Py) and A(Py)A(Py), and investigated their duplex formations and the pyrene associations.

我们合成了U(Py)U(Py)和A(Py)A(Py)两种连续序列的芘修饰RNA序列,并研究了它们的双链结构和芘的关联。
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引用次数: 0
Multiple-turnover cleavage of double-stranded DNA by sandwiched zinc-finger nuclease. 夹锌指核酸酶对双链DNA的多重翻转切割。
Pub Date : 2009-01-01 DOI: 10.1093/nass/nrp140
Yusuke Mineta, Tomoyuki Okamoto, Kosuke Takenaka, Norio Doi, Yasuhiro Aoyama, Takashi Sera

To refine zinc-finger nuclease (ZFN) technology, we constructed a sandwiched ZFN, in which a DNA cleavage enzyme was sandwiched with two artificial zinc-finger proteins (AZPs). Because the sandwiched ZFN is designed to cleave the DNA between the two AZP-binding sites, the sandwiched ZFN is expected to bind preferentially to a DNA substrate rather than to cleavage products and thereby cleave it with multiple turnovers. To prove the concept, we sandwiched a staphylococcal nuclease (SNase), which cleaves DNA as a monomer, between two 3-finger AZPs. The AZP-sandwiched SNase cleaved large amounts of dsDNA site-specifically. Such multiple-turnover cleavage was not observed with control nucleases that possess a single AZP.

为了进一步完善锌指核酸酶(ZFN)技术,我们构建了一个夹在两个人工锌指蛋白(AZPs)中间的DNA裂解酶。由于夹在中间的ZFN被设计用于在两个azp结合位点之间切割DNA,因此夹在中间的ZFN预计会优先结合DNA底物而不是切割产物,从而通过多次翻转来切割它。为了证明这一概念,我们将葡萄球菌核酸酶(SNase)夹在两个3指azp之间,SNase可以将DNA作为一个单体进行切割。夹在azp中间的SNase特异地切割了大量的dsDNA位点。具有单一AZP的对照核酸酶没有观察到这种多翻转裂解。
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引用次数: 1
期刊
Nucleic acids symposium series (2004)
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