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1. 发明申请

US20080299595A1 Tailored glycoproteomic methods for the sequencing, mapping and identification of cellular glycoproteins 有权
标题翻译：用于测序，测定和鉴定细胞糖蛋白的定制糖蛋白学方法
公开(公告)号：US20080299595A1
公开(公告)日：2008-12-04
申请号：US12079157
申请日：2008-03-24
申请人： Chi-Huey Wong , Tsui-Ling Hsu , Sarah R. Hanson
发明人： Chi-Huey Wong , Tsui-Ling Hsu , Sarah R. Hanson
IPC分类号： C12Q1/34 , C12P21/04 , C12Q1/02
CPC分类号： G01N33/582 , G01N33/6842 , G01N2400/00
摘要： The present disclosure relates to tailored glycoproteomic methods, and more particularly to methods for the sequencing, mapping and identification of cellular glycoproteins using saccharide-selective bioorthogonal probes. A method is disclosed for saccharide-selective glycoprotein identification (ID) and glycan mapping (GIDmap) that generates glycoproteins tailored with bioorthogonally tagged alkynyl saccharides that can be selectively isolated, allowing for glycoprotein ID and glycan mapping via mass spectromic proteomics, including liquid chromatography-tandmen mass spectroscopy (LC-MS2). LC-MS2 may be used to identify cellular glycans, and more specifically cancer-related glycoproteins.
摘要翻译：本公开涉及定制的糖蛋白学方法，更具体地涉及使用糖选择性生物正交探针测序，测定和鉴定细胞糖蛋白的方法。公开了糖选择性糖蛋白鉴定（ID）和聚糖测绘（GIDmap）的方法，其生成可以选择性分离的生物递归标记的炔基糖定制的糖蛋白，允许通过质谱蛋白质组学进行糖蛋白ID和聚糖测定，包括液相色谱 - 坦德质谱（LC-MS2）。 LC-MS2可用于鉴定细胞聚糖，更具体地是癌症相关糖蛋白。

2. 发明申请

US20110257376A1 GLYCOPROTEOMIC PROBES FOR FLUORESCENT IMAGING OF FUCOSYLATED GLYCANS IN VIVO 有权
标题翻译：血液中富含荧光成像的GLYCOPROTEOMIC PROBES
公开(公告)号：US20110257376A1
公开(公告)日：2011-10-20
申请号：US13053192
申请日：2011-03-21
申请人： Chi-Huey Wong , Tsui-Ling Hsu , Sarah R. Hanson , Masaaki Sawa
发明人： Chi-Huey Wong , Tsui-Ling Hsu , Sarah R. Hanson , Masaaki Sawa
IPC分类号： C07K14/47 , C07H19/207
CPC分类号： G01N33/582 , G01N1/30 , G01N2400/00
摘要： Methods are provided for labeling cellular glycans bearing azide groups via fluorescent labeling comprising Cu(I)-catalyzed [3+2] cycloaddition of a probe comprising alkynyl group. Generation of fluorescent probes from a nonfluorescent precursor, 4-ethynyl-N-ethyl-1,8-naphthalimide, by Cu(I)-catalyzed [3+2] cycloaddition of the alkyne group of the probe to an azido-modified sugar are provided. Incorporation of azido-containing fucose analog into glycoconjugates via the fucose salvage pathway are disclosed. Fluorescent visualization of fucosylated cells by flow cytometry of cells treated with 6-azidofucose labeled with click-activated fluorogenic probe or biotinylated alkyne is disclosed. Visualization of intracellular location of fucosylated glycoconjugates by fluorescence microscopy are disclosed.
摘要翻译：提供了通过含有包含炔基的探针的Cu（I）催化的[3 + 2]环加成的荧光标记来标记携带叠氮基的细胞聚糖的方法。通过Cu（I）催化的[3 + 2]环加成的探针的炔基与叠氮改性的糖，从非荧光前体4-乙炔基-N-乙基-1,8-萘二甲酰亚胺生成荧光探针是提供。公开了通过岩藻糖补救途径将叠氮基岩藻糖类似物掺入糖缀合物。公开了通过用用点击激活的荧光探针或生物素化的炔标记的6-叠氮基聚糖处理的细胞的流式细胞术的岩藻糖基化细胞的荧光可视化。公开了通过荧光显微镜观察岩藻糖基化糖缀合物的细胞内位置。

3. 发明授权

US07943330B2 Tailored glycoproteomic methods for the sequencing, mapping and identification of cellular glycoproteins 有权
标题翻译：用于测序，测定和鉴定细胞糖蛋白的定制糖蛋白学方法
公开(公告)号：US07943330B2
公开(公告)日：2011-05-17
申请号：US12079157
申请日：2008-03-24
申请人： Chi-Huey Wong , Tsui-Ling Hsu , Sarah R Hanson
发明人： Chi-Huey Wong , Tsui-Ling Hsu , Sarah R Hanson
IPC分类号： G01N33/53 , G01N31/00
CPC分类号： G01N33/582 , G01N33/6842 , G01N2400/00
摘要： The present disclosure relates to tailored glycoproteomic methods, and more particularly to methods for the sequencing, mapping and identification of cellular glycoproteins using saccharide-selective bioorthogonal probes. A method is disclosed for saccharide-selective glycoprotein identification (ID) and glycan mapping (GIDmap) that generates glycoproteins tailored with bioorthogonally tagged alkynyl saccharides that can be selectively isolated, allowing for glycoprotein ID and glycan mapping via mass spectromic proteomics, including liquid chromatography-tandmen mass spectroscopy (LC-MS2). LC-MS2 may be used to identify cellular glycans, and more specifically cancer-related glycoproteins.
摘要翻译：本公开涉及定制的糖蛋白学方法，更具体地涉及使用糖选择性生物正交探针测序，测定和鉴定细胞糖蛋白的方法。公开了糖选择性糖蛋白鉴定（ID）和聚糖测绘（GIDmap）的方法，其生成可以选择性分离的生物递归标记的炔基糖定制的糖蛋白，允许通过质谱蛋白质组学进行糖蛋白ID和聚糖测定，包括液相色谱 - 坦德质谱（LC-MS2）。 LC-MS2可用于鉴定细胞聚糖，更具体地是癌症相关糖蛋白。

4. 发明授权

US07910319B2 Glycoproteomic probes for fluorescent imaging fucosylated glycans in vivo 有权
标题翻译：用于体内荧光成像岩藻糖基化聚糖的糖蛋白质组学探针
公开(公告)号：US07910319B2
公开(公告)日：2011-03-22
申请号：US12079228
申请日：2008-03-24
申请人： Chi-Huey Wong , Tsui-Ling Hsu , Sarah R Hanson , Masaaki Sawa
发明人： Chi-Huey Wong , Tsui-Ling Hsu , Sarah R Hanson , Masaaki Sawa
IPC分类号： G01N33/53
CPC分类号： G01N33/582 , G01N1/30 , G01N2400/00
摘要： The disclosure provides a method of labeling of cellular glycans bearing azide groups via a fluorescent labeling technique based on Cu(I)-catalyzed [3+2]cycloaddition (click activation) of a probe comprising an alkynyl group. The method entails generating a fluorescent probe from a nonfluorescent precursor, 4-ethynyl-N-ethyl-1,8-naphthalimide, by Cu(I)-catalyzed [3+2]cycloaddition of the alkyne group of the probe with an azido-modified sugar. The disclosure further provides a method of incorporating an azido-containing fucose analog into glycoconjugates via the fucose salvage pathway. The disclosure provides a method of fluorescent visualization of fucosylated cells by flow cytometry when cells treated with 6-azidofucose are labeled with the click-activated fluorogenic probe or biotinylated alkyne. A method of visualizing the intracellular localization of fucosylated glycoconjugates by fluorescence microscopy is also disclosed.
摘要翻译：本公开提供了通过基于包含炔基的探针的Cu（I）催化的[3 + 2]环加成（点击活化）的荧光标记技术来标记携带叠氮基的细胞聚糖的方法。该方法需要通过Cu（I）催化的[3 + 2]环加成的探针的炔基与非荧光前体4-乙炔基-N-乙基-1,8-萘酰亚胺的生成荧光探针，改性糖。本公开进一步提供了通过岩藻糖补救途径将含叠氮基岩藻糖类似物掺入糖缀合物的方法。本公开内容提供了当用6-叠氮基聚糖处理的细胞用点击激活的荧光探针或生物素化的炔被标记时，流式细胞仪荧光显示岩藻糖基化细胞的方法。还公开了通过荧光显微镜观察岩藻糖基化糖缀合物的细胞内定位的方法。

5. 发明申请

US20080268468A1 Alkynyl sugar analogs for the labeling and visualization of glycoconjugates in cells 有权
标题翻译：炔基糖类似物用于细胞中糖缀合物的标记和可视化
公开(公告)号：US20080268468A1
公开(公告)日：2008-10-30
申请号：US12079226
申请日：2008-03-24
申请人： CHI-HUEY WONG , TSUI-LING HSU , SARAH R. HANSON
发明人： CHI-HUEY WONG , TSUI-LING HSU , SARAH R. HANSON
IPC分类号： G01N33/50 , C12P19/00 , G01N33/00 , C07H5/04 , C07K16/00 , C12Q1/02
CPC分类号： G01N33/5005 , G01N33/5008 , G01N33/533 , G01N2400/00
摘要： The present disclosure relates to a method for metabolic oligosaccharide engineering that incorporates derivatized alkyne-bearing sugar analogs as “tags” into cellular glycoconjugates. The disclosed method incorporates alkynyl derivatized Fuc and alkynyl derivatized ManNAc sugars into a cellular glycoconjugate. A chemical probe comprising an azide group and a visual probe or a fluorogenic probe is used to label the alkyne-derivatized sugar-tagged glycoconjugate. In one aspect, the chemical probe binds covalently to the alkynyl group by Cu(I)-catalyzed [3+2] azide-alkyne cycloaddition and is visualized at the cell surface, intracellularly, or in a cellular extract. The labeled glycoconjugate is capable of detection by flow cytometry, SDS-PAGE, Western blot, ELISA or confocal microscopy, and mass spectrometry.
摘要翻译：本公开内容涉及将衍生的含炔烃类似物作为“标签”掺入细胞糖缀合物的代谢寡糖工程方法。所公开的方法将炔基衍生化的Fuc和炔基衍生的ManNAc糖引入细胞糖缀合物中。使用包含叠氮化物基团和视觉探针或荧光探针的化学探针来标记炔衍生的糖标记的糖缀合物。在一个方面，化学探针通过Cu（I）催化的[3 + 2]叠氮炔环加成共价结合到炔基上，并且在细胞表面，细胞内或细胞提取物中可视化。标记的糖缀合物能够通过流式细胞术，SDS-PAGE，Western印迹，ELISA或共聚焦显微镜和质谱检测。

6. 发明申请

US20080241903A1 In vivo site-sepecific incorporation of N-acetyl-galactosamine amino acids in eubacteria 审中-公开
标题翻译： N-乙酰基半乳糖胺氨基酸在真细菌中的体内位点 - 特异性掺入
公开(公告)号：US20080241903A1
公开(公告)日：2008-10-02
申请号：US12082214
申请日：2008-04-08
申请人： Peter G. Schultz , Sarah R. Hanson , Ran Xu , Zhiwen Zhang , Chi-Huey Wong
发明人： Peter G. Schultz , Sarah R. Hanson , Ran Xu , Zhiwen Zhang , Chi-Huey Wong
IPC分类号： C12N9/00 , C12N5/06
CPC分类号： C12P21/005 , C12N9/93 , C12N15/67
摘要： Methods and compositions for making glycoproteins, both in vitro and in vivo, are provided. One method involves incorporating an unnatural amino acid having a N-acetylgalactosamine moiety into a protein; optionally, the N-acetylgalactosamine-containing unnatural amino acid can be further modified with additional sugars.
摘要翻译：提供了体外和体内制备糖蛋白的方法和组合物。一种方法包括将具有N-乙酰半乳糖胺部分的非天然氨基酸掺入蛋白质中; 任选地，含N-乙酰半乳糖胺的非天然氨基酸可以进一步用另外的糖进行改性。

7. 发明授权

US07378263B2 In vivo site-specific incorporation of N-acetyl-galactosamine amino acids in eubacteria 失效
标题翻译： N-乙酰半乳糖胺氨基酸在真细菌中的体内位点特异性掺入
公开(公告)号：US07378263B2
公开(公告)日：2008-05-27
申请号：US11255601
申请日：2005-10-20
申请人： Peter G. Schultz , Sarah R. Hanson , Ran Xu , Zhiwen Zhang , Chi-Heuy Wong
发明人： Peter G. Schultz , Sarah R. Hanson , Ran Xu , Zhiwen Zhang , Chi-Heuy Wong
IPC分类号： C12N9/10 , C12N15/12 , C12N15/54 , C12P21/00
CPC分类号： C12P21/005 , C12N9/93 , C12N15/67
摘要： Methods and compositions for making glycoproteins, both in vitro and in vivo, are provided. One method involves incorporating an unnatural amino acid having a N-acetylgalactosamine moiety into a protein; optionally, the N-acetylgalactosamine-containing unnatural amino acid can be further modified with additional sugars.
摘要翻译：提供了体外和体内制备糖蛋白的方法和组合物。一种方法包括将具有N-乙酰半乳糖胺部分的非天然氨基酸掺入蛋白质中; 任选地，含N-乙酰半乳糖胺的非天然氨基酸可以进一步用另外的糖进行改性。

8. 发明授权

US08329413B2 Glycoproteomic probes for fluorescent imaging of fucosylated glycans in vivo 有权
标题翻译：用于体内岩藻糖基化聚糖荧光成像的糖蛋白质组学探针
公开(公告)号：US08329413B2
公开(公告)日：2012-12-11
申请号：US13053192
申请日：2011-03-21
申请人： Chi-Huey Wong , Tsui-Ling Hsu , Sarah R Hanson , Masaaki Sawa
发明人： Chi-Huey Wong , Tsui-Ling Hsu , Sarah R Hanson , Masaaki Sawa
IPC分类号： G01N33/53
CPC分类号： G01N33/582 , G01N1/30 , G01N2400/00
摘要： Methods are provided for labeling cellular glycans bearing azide groups via fluorescent labeling comprising Cu(I)-catalyzed [3+2] cycloaddition of a probe comprising alkynyl group. Generation of fluorescent probes from a nonfluorescent precursor, 4-ethynyl-N-ethyl-1,8-naphthalimide, by Cu(I)-catalyzed [3+2] cycloaddition of the alkyne group of the probe to an azido-modified sugar are provided. Incorporation of azido-containing fucose analog into glycoconjugates via the fucose salvage pathway are disclosed. Fluorescent visualization of fucosylated cells by flow cytometry of cells treated with 6-azidofucose labeled with click-activated fluorogenic probe or biotinylated alkyne is disclosed. Visualization of intracellular location of fucosylated glycoconjugates by fluorescence microscopy are disclosed.
摘要翻译：提供了通过含有包含炔基的探针的Cu（I）催化的[3 + 2]环加成的荧光标记来标记携带叠氮基的细胞聚糖的方法。通过Cu（I）催化的[3 + 2]环加成的探针的炔基与叠氮改性的糖，从非荧光前体4-乙炔基-N-乙基-1,8-萘二甲酰亚胺生成荧光探针是提供。公开了通过岩藻糖补救途径将叠氮基岩藻糖类似物掺入糖缀合物。公开了通过用用点击激活的荧光探针或生物素化的炔标记的6-叠氮基聚糖处理的细胞的流式细胞术的岩藻糖基化细胞的荧光可视化。公开了通过荧光显微镜观察岩藻糖基化糖缀合物的细胞内位置。

9. 发明申请

US20080241856A1 Glycoproteomic probes for fluorescent imaging of fucosylated glycans in vivo 有权
标题翻译：用于体内岩藻糖基化聚糖荧光成像的糖蛋白质组学探针
公开(公告)号：US20080241856A1
公开(公告)日：2008-10-02
申请号：US12079228
申请日：2008-03-24
申请人： Chi-Huey Wong , Tsui-Ling Hsu , Sarah R. Hanson , Masaaki Sawa
发明人： Chi-Huey Wong , Tsui-Ling Hsu , Sarah R. Hanson , Masaaki Sawa
IPC分类号： G01N33/53 , C12P19/44 , C12Q1/00
CPC分类号： G01N33/582 , G01N1/30 , G01N2400/00
摘要： The disclosure provides a method of labeling of cellular glycans bearing azide groups via a fluorescent labeling technique based on Cu(I)-catalyzed [3+2]cycloaddition (click activation) of a probe comprising an alkynyl group. The method entails generating a fluorescent probe from a nonfluorescent precursor, 4-ethynyl-N-ethyl-1,8-naphthalimide, by Cu(I)-catalyzed [3+2]cycloaddition of the alkyne group of the probe with an azido-modified sugar. The disclosure further provides a method of incorporating an azido-containing fucose analog into glycoconjugates via the fucose salvage pathway. The disclosure provides a method of fluorescent visualization of fucosylated cells by flow cytometry when cells treated with 6-azidofucose are labeled with the click-activated fluorogenic probe or biotinylated alkyne. A method of visualizing the intracellular localization of fucosylated glycoconjugates by fluorescence microscopy is also disclosed.
摘要翻译：本公开提供了通过基于包含炔基的探针的Cu（I）催化的[3 + 2]环加成（点击活化）的荧光标记技术来标记携带叠氮基的细胞聚糖的方法。该方法需要通过Cu（I）催化的[3 + 2]环加成的探针的炔基与非荧光前体4-乙炔基-N-乙基-1,8-萘酰亚胺的生成荧光探针，改性糖。本公开进一步提供了通过岩藻糖补救途径将含叠氮基岩藻糖类似物掺入糖缀合物的方法。本公开内容提供了当用6-叠氮基聚糖处理的细胞用点击激活的荧光探针或生物素化的炔被标记时，流式细胞仪荧光显示岩藻糖基化细胞的方法。还公开了通过荧光显微镜观察岩藻糖基化糖缀合物的细胞内定位的方法。

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