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1. 发明申请

US20130085271A1 POST-SYNTHETIC MODIFICATION OF NUCLEIC ACIDS BY INVERSE DIELS-ALDER REACTION 有权
标题翻译：逆转反应对核酸的合成修饰
公开(公告)号：US20130085271A1
公开(公告)日：2013-04-04
申请号：US13557698
申请日：2012-07-25
申请人： Manfred WIESSLER , Peter Lorenz , Heinz Fleischhacker , Christian Kliem , Andres Jäschke , Juliane Schoch
发明人： Manfred WIESSLER , Peter Lorenz , Heinz Fleischhacker , Christian Kliem , Andres Jäschke , Juliane Schoch
IPC分类号： C07H1/00
CPC分类号： C07H1/00 , C07H21/00 , C07H21/04
摘要： The present invention concerns a method and a kit for the post-synthetic modification of nucleic acids via an inverse Diels-Alder reaction.
摘要翻译：本发明涉及通过反Diels-Alder反应对核酸进行后合成修饰的方法和试剂盒。

2. 发明授权

US09169283B2 Post-synthetic modification of nucleic acids by inverse diels-alder reaction 有权
标题翻译：通过反向diels-alder反应对核酸进行后合成修饰
公开(公告)号：US09169283B2
公开(公告)日：2015-10-27
申请号：US13557698
申请日：2012-07-25
申请人： Manfred Wiessler , Peter Lorenz , Heinz Fleischhacker , Karola Ursula Fleischhacker , Marlen Fleischhacker , Nadja Fleischhacker , Christian Kliem , Andres Jäschke , Juliane Schoch
发明人： Manfred Wiessler , Peter Lorenz , Heinz Fleischhacker , Christian Kliem , Andres Jäschke , Juliane Schoch
IPC分类号： C07H21/04 , C07H21/00 , C07H1/00
CPC分类号： C07H1/00 , C07H21/00 , C07H21/04
摘要： The present invention concerns a method and a kit for the post-synthetic modification of nucleic acids via an inverse Diels-Alder reaction.
摘要翻译：本发明涉及通过反Diels-Alder反应对核酸进行后合成修饰的方法和试剂盒。

3. 发明申请

US20150218203A1 MULTIPLE ORTHOGONAL LABELLING OF OLIGONUCLEOTIDES 有权
标题翻译：寡核苷酸的多重正交标记
公开(公告)号：US20150218203A1
公开(公告)日：2015-08-06
申请号：US14342021
申请日：2012-08-31
申请人： Juliane Becker , Andres Jäschke , Ayan Samanta , Manfred Wiessler
发明人： Juliane Becker , Andres Jäschke , Ayan Samanta , Manfred Wiessler
IPC分类号： C07H21/00
CPC分类号： C07H21/00
摘要： In summary, the present invention concerns a method for multiple orthogonal labelling of oligonucleotides, preferably RNA or DNA, by simultaneously performing the inverse Diels-Alder reaction (DAinv) and the copper-catalyzed click reaction (CuAAC), wherein the method is employed in a single step by just adding the different reaction components together and incubating the aqueous reaction mixture preferably for one hour at room temperature. In detail, the reaction components are one or more N3-modified labels, a copper compound, a stabilizing ligand, a reducing agent and one or more electron-deficient label-modified dienes that are added together with an at least double-modified oligonucleotide having one more nucleotides containing one or more N3-reactive groups and one or more electron-rich dienophiles, wherein a terminal alkyne moiety is preferably used as N3-reactive group(s) and a frans-cyclooctene moiety or norbornene is preferably used as electron-rich dienophile(s), more preferably frans-cyclooctene. Therefore, the present invention provides a one-pot method for post-synthetic multiple orthogonal labeling of oligonucleotides, which allows the site-specific introduction of more than one label, preferably of at least two labels into oligonucleotides after solid-phase synthesis, wherein the DAinv takes place on the dienophile modification only and the CuAAC selectively takes place on the N3-reactive group modification.
摘要翻译：总之，本发明涉及通过同时进行反狄尔斯 - 阿尔德反应（DAinv）和铜催化的咔嗒反应（CuAAC）来对寡核苷酸，优选RNA或DNA进行多重正交标记的方法，其中该方法用于通过仅将不同的反应组分加入一起并将该水性反应混合物在室温下温育1小时来进行单步骤。详细地，反应成分是与至少双修饰寡核苷酸一起加入的一种或多种N 3修饰标记，铜化合物，稳定配体，还原剂和一种或多种电子缺陷型标记修饰的二烯，另外还有一个含有一个或多个N 3 - 反应性基团和一个或多个富电子基性亲核体的核苷酸，其中末端炔部分优选用作N 3反应性基团，并且优选使用反式 - 环辛烯部分或降冰片烯作为电子 - 富含亲二烯体，更优选为反式环辛烯。因此，本发明提供了一种用于寡核苷酸的后合成多重正交标记的一锅法，其允许在固相合成之后将多于一个标记，优选至少两个标记的位点特异性引入寡核苷酸，其中 DAinv仅在亲双烯体修饰上发生，CuAAC选择性地发生在N 3反应性基团修饰上。

4. 发明授权

US09315537B2 Multiple orthogonal labelling of oligonucleotides 有权
标题翻译：寡核苷酸的多重正交标记
公开(公告)号：US09315537B2
公开(公告)日：2016-04-19
申请号：US14342021
申请日：2012-08-31
申请人： Juliane Becker , Andres Jäschke , Ayan Samanta , Manfred Wiessler
发明人： Juliane Becker , Andres Jäschke , Ayan Samanta , Manfred Wiessler
IPC分类号： C07H19/04 , C07H21/00
CPC分类号： C07H21/00
摘要： In summary, the present invention concerns a method for multiple orthogonal labelling of oligonucleotides, preferably RNA or DNA, by simultaneously performing the inverse Diels-Alder reaction (DAinv) and the copper-catalyzed click reaction (CuAAC), wherein the method is employed in a single step by just adding the different reaction components together and incubating the aqueous reaction mixture preferably for one hour at room temperature. In detail, the reaction components are one or more N3-modified labels, a copper compound, a stabilizing ligand, a reducing agent and one or more electron-deficient label-modified dienes that are added together with an at least double-modified oligonucleotide having one more nucleotides containing one or more N3-reactive groups and one or more electron-rich dienophiles, wherein a terminal alkyne moiety is preferably used as N3-reactive group(s) and a frans-cyclooctene moiety or norbornene is preferably used as electron-rich dienophile(s), more preferably frans-cyclooctene. Therefore, the present invention provides a one-pot method for post-synthetic multiple orthogonal labeling of oligonucleotides, which allows the site-specific introduction of more than one label, preferably of at least two labels into oligonucleotides after solid-phase synthesis, wherein the DAinv takes place on the dienophile modification only and the CuAAC selectively takes place on the N3-reactive group modification.
摘要翻译：总之，本发明涉及通过同时进行反狄尔斯 - 阿尔德反应（DAinv）和铜催化的咔嗒反应（CuAAC）来对寡核苷酸（优选RNA或DNA）进行多重正交标记的方法，其中该方法用于通过仅将不同的反应组分加入一起并将该水性反应混合物在室温下温育1小时来进行单步骤。详细地，反应成分是与至少双修饰寡核苷酸一起加入的一种或多种N 3修饰标记，铜化合物，稳定配体，还原剂和一种或多种电子缺陷型标记修饰的二烯，另外还有一个含有一个或多个N 3 - 反应性基团和一个或多个富电子基性亲核体的核苷酸，其中末端炔部分优选用作N 3反应性基团，并且优选使用反式 - 环辛烯部分或降冰片烯作为电子 - 富含亲二烯体，更优选为反式环辛烯。因此，本发明提供了一种用于寡核苷酸的后合成多重正交标记的一锅法，其允许在固相合成之后将多于一个标记，优选至少两个标记的位点特异性引入寡核苷酸，其中 DAinv仅在亲双烯体修饰上发生，CuAAC选择性地发生在N 3反应性基团修饰上。

5. 发明授权

US07160680B2 Mutation analysis by mass spectrometry using photolytically cleavable primers 有权
标题翻译：使用光解性切割引物的质谱进行突变分析
公开(公告)号：US07160680B2
公开(公告)日：2007-01-09
申请号：US10079043
申请日：2002-02-20
申请人： Markus Kostrzewa , Thomas Fröhlich , Thomas Wenzel , Andres Jäschke , Felix Hausch
发明人： Markus Kostrzewa , Thomas Fröhlich , Thomas Wenzel , Andres Jäschke , Felix Hausch
IPC分类号： C12Q1/68 , C12P19/34
CPC分类号： C12Q1/6858 , C12Q2565/627 , C12Q2523/319
摘要： The invention relates to a method of a mass-spectrometric analysis of known mutation sites in the genome, such as single nucleotide polymorphisms (SNPs), using the method of restricted primer extension. The invention consists of the use of primers with a photocleavable linker. The linker creates a gap in a DNA strand which is almost the same size as a natural DNA building block (nucleoside). The linker forms a bridge over a base pair without inhibiting hybridization or enzymatic extension. However, the linker allows the primers to be cleaved after extension in order to obtain short DNA fragments which can be more easily detected on the mass spectrometer.
摘要翻译：本发明涉及使用限制性引物延伸的方法对基因组中已知突变位点进行质谱分析的方法，例如单核苷酸多态性（SNP）。本发明包括使用具有光可透洗接头的引物。接头在DNA链中产生与天然DNA构建块（核苷）几乎相同大小的间隙。连接体在碱基对上形成桥，而不抑制杂交或酶促延伸。然而，接头允许引物在延伸后被切割，以获得在质谱仪上更容易检测到的短DNA片段。

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