Current Protocols in Nucleic Acid Chemistry最新文献

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Synthesis of γ-Phosphate-Labeled and Doubly Labeled Adenosine Triphosphate Analogs γ-磷酸标记和双标记三磷酸腺苷类似物的合成
Current Protocols in Nucleic Acid Chemistry Pub Date : 2018-02-15 DOI: 10.1002/0471142700.nc1314s60
Stephan M. Hacker, Moritz Welter, Andreas Marx
{"title":"Synthesis of γ-Phosphate-Labeled and Doubly Labeled Adenosine Triphosphate Analogs","authors":"Stephan M. Hacker,&nbsp;Moritz Welter,&nbsp;Andreas Marx","doi":"10.1002/0471142700.nc1314s60","DOIUrl":"10.1002/0471142700.nc1314s60","url":null,"abstract":"<p>This unit describes the synthesis of γ-phosphate-labeled and doubly labeled adenosine triphosphate (ATP) analogs and their characterization using the phosphodiesterase I from <i>Crotalus adamanteus</i> (snake venom phosphodiesterase; SVPD). In the key step of the synthesis, ATP or an ATP analog, bearing a linker containing a trifluoroacetamide group attached to the nucleoside, are modified with an azide-containing linker at the terminal phosphate using an alkylation reaction. Subsequently, different labels are introduced to the linkers by transformation of one functional group to an amine and coupling to an <i>N</i>-hydroxysuccinimide ester. Specifically, the Staudinger reaction of the azide is employed as a straightforward means to obtain an amine in the presence of various labels. Furthermore, the fluorescence characteristics of a fluorogenic, doubly labeled ATP analog are investigated following enzymatic cleavage by SVPD. © 2015 by John Wiley &amp; Sons, Inc.</p>","PeriodicalId":10966,"journal":{"name":"Current Protocols in Nucleic Acid Chemistry","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2018-02-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/0471142700.nc1314s60","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"33116872","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 2
Probing RNA Folding Pathways by RNA Fingerprinting 利用RNA指纹技术探测RNA折叠途径
Current Protocols in Nucleic Acid Chemistry Pub Date : 2018-02-13 DOI: 10.1002/cpnc.36
Sarah A. Woodson
{"title":"Probing RNA Folding Pathways by RNA Fingerprinting","authors":"Sarah A. Woodson","doi":"10.1002/cpnc.36","DOIUrl":"10.1002/cpnc.36","url":null,"abstract":"<p>This unit provides protocols for using native polyacrylamide gel electrophoresis to distinguish folding and unfolding conformers of RNA. It is useful for studying conformers that can exchange in a period of minutes or seconds, and that are thus difficult to study by solution-based methods. Conformers that have been separated and immobilized in the gel matrix can be used to study catalytic activity with or without being eluted from the gel. The method can be applied to a wide variety of catalytic RNAs and RNA-protein complexes. © 2017 by John Wiley &amp; Sons, Inc.</p>","PeriodicalId":10966,"journal":{"name":"Current Protocols in Nucleic Acid Chemistry","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2018-02-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/cpnc.36","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"35522061","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Determining Functional Aptamer-Protein Interaction by Biolayer Interferometry 生物层干涉法测定功能适配体-蛋白质相互作用
Current Protocols in Nucleic Acid Chemistry Pub Date : 2018-02-13 DOI: 10.1002/cpnc.18
Xinhui Lou, Martin Egli, Xianbin Yang
{"title":"Determining Functional Aptamer-Protein Interaction by Biolayer Interferometry","authors":"Xinhui Lou,&nbsp;Martin Egli,&nbsp;Xianbin Yang","doi":"10.1002/cpnc.18","DOIUrl":"10.1002/cpnc.18","url":null,"abstract":"<p>Short single-stranded nucleic acids called aptamers are widely being explored as recognition molecules of high affinity and specificity for binding a wide range of target molecules, particularly protein targets. In biolayer interferometry (BLI), a simple Dip-and-Read approach in which the aptamer-coated biosensors are dipped into microplate wells is used to study the interactions between an aptamer and its target protein. Here we describe the protocol for the analysis of the interaction between a well-characterized anti-thrombin RNA aptamer with thrombin (Basic Protocol). We also report on the protocol for the affinity screening of a panel of anti-thrombin RNA aptamers with a single phosphorodithioate (PS2) modification, whereby the position of the modification along the RNA backbone is varied systematically (Support Protocol). The PS2 modification uses two sulfur atoms to replace two non-bridging oxygen atoms at an internucleotide phosphodiester backbone linkage. The PS2-modified RNAs are nuclease resistant and several in vitro and in vivo assays have demonstrated their biological activity. For example, combining the PS2 with the 2′-OMe modification affords increased loading of modified small interfering RNA (siRNA) duplexes into the RNA-induced silencing complex (RISC) as well as enhanced gene-silencing antitumor activity. © 2016 by John Wiley &amp; Sons, Inc.</p>","PeriodicalId":10966,"journal":{"name":"Current Protocols in Nucleic Acid Chemistry","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2018-02-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/cpnc.18","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"50902276","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 20
Vibration Ball Milling for the Synthesis of 5′-Thioadenosine 5′-Pyrophosphate (P′→5′) Adenosine (dASppA) 振动球磨法合成5′-硫代腺苷5′-焦磷酸(P′→5′)腺苷(dASppA)
Current Protocols in Nucleic Acid Chemistry Pub Date : 2018-02-13 DOI: 10.1002/cpnc.37
Olga Eguaogie, Joseph S. Vyle
{"title":"Vibration Ball Milling for the Synthesis of 5′-Thioadenosine 5′-Pyrophosphate (P′→5′) Adenosine (dASppA)","authors":"Olga Eguaogie,&nbsp;Joseph S. Vyle","doi":"10.1002/cpnc.37","DOIUrl":"10.1002/cpnc.37","url":null,"abstract":"<p>Using vibration ball milling, 5′-chloro-5′-deoxyadenosine (CldA) reacts cleanly with 4-methoxybenzyl mercaptan (MobSH), under basic conditions, to the corresponding thioether (MobSdA), which is isolated following precipitation and trituration. Under acidic conditions, in a one-pot, two-step process, MobSdA is transformed into 5′-deoxy-5′-(5-nitropyridyl-2-disulfanyl)-adenosine (NPySSdA). Michaelis-Arbuzov (M-A) reaction of NPySSdA with tris(trimethylsilyl) phosphite proceeds to completion within 30 min as determined by <sup>31</sup>P NMR, and the persilylated M-A product thus formed can be stored in solution under anhydrous conditions at room temperature for several days (in contrast, the anionic phosphorothiolate monoester is labile to hydrolysis). Following evaporation, mechanochemical mixing of the crude M-A product with the nucleotide donor adenosine 5′-monophosphomorpholidate under acidic activation in the presence of additional water gives rapid hydrolytic desilylation and phosphate coupling, so that essentially complete reaction is observed after 90 min and dASppA isolated following C-18 reversed phase HPLC and desalting (&gt;99% pure as determined by monitoring at 260 nm). © 2017 by John Wiley &amp; Sons, Inc.</p>","PeriodicalId":10966,"journal":{"name":"Current Protocols in Nucleic Acid Chemistry","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2018-02-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/cpnc.37","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"35419190","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 4
Synthesis of the Phosphoramidite Units for Benzene-Glycol Nucleic Acid 苯乙二醇核酸酰胺磷酸基的合成
Current Protocols in Nucleic Acid Chemistry Pub Date : 2018-02-13 DOI: 10.1002/cpnc.38
Yusuke Maeda, Nazuki Niwa, Yoshihito Ueno
{"title":"Synthesis of the Phosphoramidite Units for Benzene-Glycol Nucleic Acid","authors":"Yusuke Maeda,&nbsp;Nazuki Niwa,&nbsp;Yoshihito Ueno","doi":"10.1002/cpnc.38","DOIUrl":"10.1002/cpnc.38","url":null,"abstract":"<p>Benzene-glycol nucleic acid-DNA chimeras form thermally and thermodynamically stable duplexes with complementary RNAs, and have base-discriminating abilities. This unit describes the synthesis of four nucleoside analogs, an adenine, cytosine, thymine, and guanine analogs with base-benzene-glycol structure. The synthesis starts with conversion of (<i>S</i>)-mandelic acid in arylboronic acid derivative, common intermediate. Nucleobase coupling of the intermediate and phosphitylation afford to phosphoroamidite units. © 2017 by John Wiley &amp; Sons, Inc.</p>","PeriodicalId":10966,"journal":{"name":"Current Protocols in Nucleic Acid Chemistry","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2018-02-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/cpnc.38","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"35522065","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Nucleoside-O-Methyl-(H)-Phosphinates: Novel Monomers for the Synthesis of Methylphosphonate Oligonucleotides Using H-Phosphonate Chemistry 核苷- o -甲基-(H)-膦酸盐:用H-膦酸盐化学合成甲基膦酸寡核苷酸的新单体
Current Protocols in Nucleic Acid Chemistry Pub Date : 2018-02-13 DOI: 10.1002/cpnc.35
Ondřej Kostov, Ondřej Páv, Ivan Rosenberg
{"title":"Nucleoside-O-Methyl-(H)-Phosphinates: Novel Monomers for the Synthesis of Methylphosphonate Oligonucleotides Using H-Phosphonate Chemistry","authors":"Ondřej Kostov,&nbsp;Ondřej Páv,&nbsp;Ivan Rosenberg","doi":"10.1002/cpnc.35","DOIUrl":"10.1002/cpnc.35","url":null,"abstract":"<p>This unit comprises the straightforward synthesis of protected 2′-deoxyribonucleoside-<i>O</i>-methyl-(H)-phosphinates in both 3′- and 5′-series. These compounds represent a new class of monomers compatible with the solid-phase synthesis of oligonucleotides using H-phosphonate chemistry and are suitable for the preparation of both 3′- and 5′-<i>O</i>-methylphosphonate oligonucleotides. The synthesis of 4-toluenesulfonyloxymethyl-(H)-phosphinic acid as a new reagent for the preparation of <i>O</i>-methyl-(H)-phosphinic acid derivatives is described. © 2017 by John Wiley &amp; Sons, Inc.</p>","PeriodicalId":10966,"journal":{"name":"Current Protocols in Nucleic Acid Chemistry","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2018-02-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/cpnc.35","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"35522062","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 1
Practical Synthesis of 4′-Thioribonucleosides from L-Arabinose via Novel Reductive Ring-Contraction Reaction and Pummerer-Type Thioglycosylation 以l -阿拉伯糖为原料,通过新型还原环收缩反应和pummer型硫代糖基化合成4′-硫代核糖核苷
Current Protocols in Nucleic Acid Chemistry Pub Date : 2018-02-13 DOI: 10.1002/cpnc.45
Hideaki Wakamatsu, Kozue Nitta, Nozomi Shoji, Yoshihiro Natori, Yukako Saito, Yuichi Yoshimura
{"title":"Practical Synthesis of 4′-Thioribonucleosides from L-Arabinose via Novel Reductive Ring-Contraction Reaction and Pummerer-Type Thioglycosylation","authors":"Hideaki Wakamatsu,&nbsp;Kozue Nitta,&nbsp;Nozomi Shoji,&nbsp;Yoshihiro Natori,&nbsp;Yukako Saito,&nbsp;Yuichi Yoshimura","doi":"10.1002/cpnc.45","DOIUrl":"10.1002/cpnc.45","url":null,"abstract":"<p>The detailed practical synthesis of 4′-thionucleosides starting from <span>L</span>-arabinose is described here. 1,4-Anhydro-2,3-<i>O</i>-isopropylidene-4-thioribitol, which is the key intermediate for the synthesis of 4′-thionucleosides, is obtained from <span>L</span>-arabinose in several steps, including a novel reductive ring-contraction reaction. After oxidation of the key intermediate, the sulfoxide is subjected to Pummerer-type thioglycosylation in the presence of persilylated nucleobases to obtain the 4′-thioribonucleosides in good yield and β-selectively. © 2017 by John Wiley &amp; Sons, Inc.</p>","PeriodicalId":10966,"journal":{"name":"Current Protocols in Nucleic Acid Chemistry","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2018-02-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/cpnc.45","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"35686183","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 1
Synthesis of 4′-Selenoribonucleosides, the Building Blocks of 4′-SelenoRNA, Using a Hypervalent Iodine 利用高价碘合成4′-硒核苷,作为4′-硒核苷的组成部分
Current Protocols in Nucleic Acid Chemistry Pub Date : 2018-02-13 DOI: 10.1002/cpnc.34
Noriko Saito-Tarashima, Masashi Ota, Noriaki Minakawa
{"title":"Synthesis of 4′-Selenoribonucleosides, the Building Blocks of 4′-SelenoRNA, Using a Hypervalent Iodine","authors":"Noriko Saito-Tarashima,&nbsp;Masashi Ota,&nbsp;Noriaki Minakawa","doi":"10.1002/cpnc.34","DOIUrl":"10.1002/cpnc.34","url":null,"abstract":"<p>Herein is described a detailed protocol for the synthesis of 4′-selenoribonucleoside derivatives that involves the use of a hypervalent iodine species. These derivatives are versatile units for the preparation of 4′-selenoRNA. Large-scale synthesis of a 4-selenosugar starting from <span>D</span>-ribose is achieved in eight steps, including a final chromatographic purification. The resulting 4-selenosugar is then subjected to the one-pot Pummerer-like reaction using hypervalent iodine in the presence of silylated nucleobases. The reaction with silylated uracil affords the desired 4′-selenouridine derivatives with excellent β-selectivity and in good yield. Conversely, when purine nucleobases are used in the Pummerer-like reaction, N7 4′-selenoribonucleoside isomers are obtained alongside the desired N9 isomers. However, the undesired N7 isomers can be converted to the desired N9 ones under acidic conditions. © 2017 by John Wiley &amp; Sons, Inc.</p>","PeriodicalId":10966,"journal":{"name":"Current Protocols in Nucleic Acid Chemistry","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2018-02-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/cpnc.34","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"35522064","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 4
3′-O-Caged 2′-Deoxynucleoside Triphosphates for Light-Mediated, Enzyme-Catalyzed, Template-Independent DNA Synthesis 3 ' -O-Caged 2 ' -脱氧核苷三磷酸光介导,酶催化,模板非依赖性DNA合成
Current Protocols in Nucleic Acid Chemistry Pub Date : 2018-02-13 DOI: 10.1002/cpnc.41
Anu Stella Mathews, Haikang Yang, Carlo Montemagno
{"title":"3′-O-Caged 2′-Deoxynucleoside Triphosphates for Light-Mediated, Enzyme-Catalyzed, Template-Independent DNA Synthesis","authors":"Anu Stella Mathews,&nbsp;Haikang Yang,&nbsp;Carlo Montemagno","doi":"10.1002/cpnc.41","DOIUrl":"10.1002/cpnc.41","url":null,"abstract":"<p>Synthesis, purification, and characterization of 3′-<i>O</i>-caged 2′-deoxyribonucleoside triphosphates (dNTPs), namely 3′-<i>O</i>-(2-nitrobenzyl)-2′-deoxy ribonucleoside triphosphates (NB-dNTPs) and 3′-<i>O</i>-(4,5-dimethoxy-2-nitrobenzyl)-2′-deoxy ribonucleoside triphosphates (DMNB-dNTPs), are discussed in detail. A total of eight 3′-<i>O</i>-caged dNTPs are synthesized with specific protocols depending on the nitrogenous base on the first carbon, i.e., adenine, guanine, thymine, and cytosine, as well as the photo-cleavable group, i.e, 2-nitrobenzyl and 4,5- dimethoxy-2-nitrobenzyl, to be attached in the 3′-<i>O</i> position. The purification of the synthesized compounds is done using ion-exchange and flash chromatography; this is followed by structural confirmation by nuclear magnetic resonance (NMR) and mass spectroscopy (MS). The efficiency of the designed compounds is tested by conducting and evaluating UV-cleaving experiments at 365 nm with proton NMR and LC-MS curves. Finally, the application of the 3′-<i>O</i>-cagged dNTPs in template-independent, enzyme-catalyzed, photo-mediated oligonucleotide synthesis is demonstrated. © 2017 by John Wiley &amp; Sons, Inc.</p>","PeriodicalId":10966,"journal":{"name":"Current Protocols in Nucleic Acid Chemistry","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2018-02-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/cpnc.41","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"35686182","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 10
Palladium-Catalyzed Synthesis of (E)-5-(3-Aminoallyl)-Uridine-5′-O-Triphosphates 钯催化合成(E)-5-(3-氨基烯丙基)-尿苷-5′- o -三磷酸酯
Current Protocols in Nucleic Acid Chemistry Pub Date : 2018-02-13 DOI: 10.1002/cpnc.42
Muthian Shanmugasundaram, Annamalai Senthilvelan, Anilkumar R. Kore
{"title":"Palladium-Catalyzed Synthesis of (E)-5-(3-Aminoallyl)-Uridine-5′-O-Triphosphates","authors":"Muthian Shanmugasundaram,&nbsp;Annamalai Senthilvelan,&nbsp;Anilkumar R. Kore","doi":"10.1002/cpnc.42","DOIUrl":"10.1002/cpnc.42","url":null,"abstract":"<p>This unit describes a simple, reliable, and efficient chemical method for the synthesis of 5-(3-aminoallyl)-2′-deoxyuridine-5′-<i>O</i>-triphosphate (AA-dUTP) and 5-(3-aminoallyl)-uridine-5′-<i>O</i>-triphosphate (AA-UTP), starting from the corresponding nucleoside triphosphate. The presented strategy involves regioselective iodination of nucleoside triphosphate using <i>N</i>-iodosuccinimide followed by the palladium-catalyzed Heck coupling with allylamine to provide the corresponding (<i>E</i>)-5-aminoallyl-uridine-5′-<i>O</i>-triphosphate in good yields. It is noteworthy that the protocol not only provides a high-purity product but also eliminates the use of toxic mercuric reagents. © 2017 by John Wiley &amp; Sons, Inc.</p>","PeriodicalId":10966,"journal":{"name":"Current Protocols in Nucleic Acid Chemistry","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2018-02-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/cpnc.42","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"35686181","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 1
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