Artificial Cysteine S‐Glycosylation Induced by Per‐O‐Acetylated Unnatural Monosaccharides during Metabolic Glycan Labeling
The unexpected, non‐enzymatic S‐glycosylation of cysteine residues in various proteins by per‐O‐acetylated monosaccharides is described. This artificial S‐glycosylation greatly compromises the specificity and validity of metabolic glycan labeling in living cells by per‐O‐acetylated azido and alkynyl...
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| Veröffentlicht in: | Angewandte Chemie 2018-02, Vol.130 (7), p.1835-1838 |
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| creator | Qin, Wei Qin, Ke Fan, Xinqi Peng, Linghang Hong, Weiyao Zhu, Yuntao Lv, Pinou Du, Yifei Huang, Rongbing Han, Mengting Cheng, Bo Liu, Yuan Zhou, Wen Wang, Chu Chen, Xing |
| description | The unexpected, non‐enzymatic S‐glycosylation of cysteine residues in various proteins by per‐O‐acetylated monosaccharides is described. This artificial S‐glycosylation greatly compromises the specificity and validity of metabolic glycan labeling in living cells by per‐O‐acetylated azido and alkynyl sugars, which has been overlooked in the field for decades. It is demonstrated that the use of unacetylated unnatural sugars can avoid the artifact formation and a corrected list of O‐GlcNAcylated proteins and O‐GlcNAc sites in HeLa cells has been assembled by using N‐azidoacetylgalactosamine (GalNAz).
Per‐O‐acetylierte Monosaccharide induzieren die nichtenzymatische Cystein‐S‐Glykosylierung von verschiedenen Proteinen. Dieser künstliche Prozess hat großen Einfluss auf die metabolische Glykanmarkierung in lebenden Zellen, kann aber durch die Verwendung nichtacetylierter nichtnatürlicher Zucker umgangen werden. Mithilfe von GalNAz wurde eine korrigierte Liste O‐GlcNAcylierter Proteine und O‐GlcNAc‐Stellen in HeLa‐Zellen erstellt. |
| doi_str_mv | 10.1002/ange.201711710 |
| format | Article |
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Per‐O‐acetylierte Monosaccharide induzieren die nichtenzymatische Cystein‐S‐Glykosylierung von verschiedenen Proteinen. Dieser künstliche Prozess hat großen Einfluss auf die metabolische Glykanmarkierung in lebenden Zellen, kann aber durch die Verwendung nichtacetylierter nichtnatürlicher Zucker umgangen werden. Mithilfe von GalNAz wurde eine korrigierte Liste O‐GlcNAcylierter Proteine und O‐GlcNAc‐Stellen in HeLa‐Zellen erstellt.</description><identifier>ISSN: 0044-8249</identifier><identifier>EISSN: 1521-3757</identifier><identifier>DOI: 10.1002/ange.201711710</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Chemistry ; Chemoproteomik ; Cysteine ; Glycan ; Glycosylation ; Labeling ; Markierung ; Metabolism ; Monosaccharides ; Nichtnatürliche Monosaccharide ; O-GlcNAc ; Proteins ; S-Glykosylierungen ; Sugar</subject><ispartof>Angewandte Chemie, 2018-02, Vol.130 (7), p.1835-1838</ispartof><rights>2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c1620-54a2373c14ab0531cb39a32c3255bc35816502d3825d7de920caa2aa17721b7b3</citedby><cites>FETCH-LOGICAL-c1620-54a2373c14ab0531cb39a32c3255bc35816502d3825d7de920caa2aa17721b7b3</cites><orcidid>0000-0002-3058-7370</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fange.201711710$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fange.201711710$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Qin, Wei</creatorcontrib><creatorcontrib>Qin, Ke</creatorcontrib><creatorcontrib>Fan, Xinqi</creatorcontrib><creatorcontrib>Peng, Linghang</creatorcontrib><creatorcontrib>Hong, Weiyao</creatorcontrib><creatorcontrib>Zhu, Yuntao</creatorcontrib><creatorcontrib>Lv, Pinou</creatorcontrib><creatorcontrib>Du, Yifei</creatorcontrib><creatorcontrib>Huang, Rongbing</creatorcontrib><creatorcontrib>Han, Mengting</creatorcontrib><creatorcontrib>Cheng, Bo</creatorcontrib><creatorcontrib>Liu, Yuan</creatorcontrib><creatorcontrib>Zhou, Wen</creatorcontrib><creatorcontrib>Wang, Chu</creatorcontrib><creatorcontrib>Chen, Xing</creatorcontrib><title>Artificial Cysteine S‐Glycosylation Induced by Per‐O‐Acetylated Unnatural Monosaccharides during Metabolic Glycan Labeling</title><title>Angewandte Chemie</title><description>The unexpected, non‐enzymatic S‐glycosylation of cysteine residues in various proteins by per‐O‐acetylated monosaccharides is described. This artificial S‐glycosylation greatly compromises the specificity and validity of metabolic glycan labeling in living cells by per‐O‐acetylated azido and alkynyl sugars, which has been overlooked in the field for decades. It is demonstrated that the use of unacetylated unnatural sugars can avoid the artifact formation and a corrected list of O‐GlcNAcylated proteins and O‐GlcNAc sites in HeLa cells has been assembled by using N‐azidoacetylgalactosamine (GalNAz).
Per‐O‐acetylierte Monosaccharide induzieren die nichtenzymatische Cystein‐S‐Glykosylierung von verschiedenen Proteinen. Dieser künstliche Prozess hat großen Einfluss auf die metabolische Glykanmarkierung in lebenden Zellen, kann aber durch die Verwendung nichtacetylierter nichtnatürlicher Zucker umgangen werden. Mithilfe von GalNAz wurde eine korrigierte Liste O‐GlcNAcylierter Proteine und O‐GlcNAc‐Stellen in HeLa‐Zellen erstellt.</description><subject>Chemistry</subject><subject>Chemoproteomik</subject><subject>Cysteine</subject><subject>Glycan</subject><subject>Glycosylation</subject><subject>Labeling</subject><subject>Markierung</subject><subject>Metabolism</subject><subject>Monosaccharides</subject><subject>Nichtnatürliche Monosaccharide</subject><subject>O-GlcNAc</subject><subject>Proteins</subject><subject>S-Glykosylierungen</subject><subject>Sugar</subject><issn>0044-8249</issn><issn>1521-3757</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNqFkM9KAzEQxoMoWKtXzwHPW_Nns-keS6m10KqgPS-z2bSmrElNdpG99RF8Rp_ELBU9CjMMzHzfN_BD6JqSESWE3YLd6hEjVNJY5AQNqGA04VLIUzQgJE2TMUvzc3QRwo4QkjGZD9Bh4huzMcpAjaddaLSxGj9_HT7ndadc6GpojLN4YatW6QqXHX7SPp4fY0-UbnpB3K-thab1MWTlrAug1Ct4U-mAq9Ybu8Ur3UDpaqNwHwwWL6HUdbxcorMN1EFf_cwhWt_NXqb3yfJxvphOlomiGSOJSIFxyRVNoSSCU1XyHDhTnAlRKi7GNBOEVXzMRCUrnTOiABgAlZLRUpZ8iG6OuXvv3lsdmmLnWm_jy4Lmecp7TllUjY4q5V0IXm-KvTdv4LuCkqKnXPSUi1_K0ZAfDR-m1t0_6mLyMJ_9eb8B2mmE1g</recordid><startdate>20180212</startdate><enddate>20180212</enddate><creator>Qin, Wei</creator><creator>Qin, Ke</creator><creator>Fan, Xinqi</creator><creator>Peng, Linghang</creator><creator>Hong, Weiyao</creator><creator>Zhu, Yuntao</creator><creator>Lv, Pinou</creator><creator>Du, Yifei</creator><creator>Huang, Rongbing</creator><creator>Han, Mengting</creator><creator>Cheng, Bo</creator><creator>Liu, Yuan</creator><creator>Zhou, Wen</creator><creator>Wang, Chu</creator><creator>Chen, Xing</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0002-3058-7370</orcidid></search><sort><creationdate>20180212</creationdate><title>Artificial Cysteine S‐Glycosylation Induced by Per‐O‐Acetylated Unnatural Monosaccharides during Metabolic Glycan Labeling</title><author>Qin, Wei ; Qin, Ke ; Fan, Xinqi ; Peng, Linghang ; Hong, Weiyao ; Zhu, Yuntao ; Lv, Pinou ; Du, Yifei ; Huang, Rongbing ; Han, Mengting ; Cheng, Bo ; Liu, Yuan ; Zhou, Wen ; Wang, Chu ; Chen, Xing</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c1620-54a2373c14ab0531cb39a32c3255bc35816502d3825d7de920caa2aa17721b7b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Chemistry</topic><topic>Chemoproteomik</topic><topic>Cysteine</topic><topic>Glycan</topic><topic>Glycosylation</topic><topic>Labeling</topic><topic>Markierung</topic><topic>Metabolism</topic><topic>Monosaccharides</topic><topic>Nichtnatürliche Monosaccharide</topic><topic>O-GlcNAc</topic><topic>Proteins</topic><topic>S-Glykosylierungen</topic><topic>Sugar</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Qin, Wei</creatorcontrib><creatorcontrib>Qin, Ke</creatorcontrib><creatorcontrib>Fan, Xinqi</creatorcontrib><creatorcontrib>Peng, Linghang</creatorcontrib><creatorcontrib>Hong, Weiyao</creatorcontrib><creatorcontrib>Zhu, Yuntao</creatorcontrib><creatorcontrib>Lv, Pinou</creatorcontrib><creatorcontrib>Du, Yifei</creatorcontrib><creatorcontrib>Huang, Rongbing</creatorcontrib><creatorcontrib>Han, Mengting</creatorcontrib><creatorcontrib>Cheng, Bo</creatorcontrib><creatorcontrib>Liu, Yuan</creatorcontrib><creatorcontrib>Zhou, Wen</creatorcontrib><creatorcontrib>Wang, Chu</creatorcontrib><creatorcontrib>Chen, Xing</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Angewandte Chemie</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Qin, Wei</au><au>Qin, Ke</au><au>Fan, Xinqi</au><au>Peng, Linghang</au><au>Hong, Weiyao</au><au>Zhu, Yuntao</au><au>Lv, Pinou</au><au>Du, Yifei</au><au>Huang, Rongbing</au><au>Han, Mengting</au><au>Cheng, Bo</au><au>Liu, Yuan</au><au>Zhou, Wen</au><au>Wang, Chu</au><au>Chen, Xing</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Artificial Cysteine S‐Glycosylation Induced by Per‐O‐Acetylated Unnatural Monosaccharides during Metabolic Glycan Labeling</atitle><jtitle>Angewandte Chemie</jtitle><date>2018-02-12</date><risdate>2018</risdate><volume>130</volume><issue>7</issue><spage>1835</spage><epage>1838</epage><pages>1835-1838</pages><issn>0044-8249</issn><eissn>1521-3757</eissn><abstract>The unexpected, non‐enzymatic S‐glycosylation of cysteine residues in various proteins by per‐O‐acetylated monosaccharides is described. This artificial S‐glycosylation greatly compromises the specificity and validity of metabolic glycan labeling in living cells by per‐O‐acetylated azido and alkynyl sugars, which has been overlooked in the field for decades. It is demonstrated that the use of unacetylated unnatural sugars can avoid the artifact formation and a corrected list of O‐GlcNAcylated proteins and O‐GlcNAc sites in HeLa cells has been assembled by using N‐azidoacetylgalactosamine (GalNAz).
Per‐O‐acetylierte Monosaccharide induzieren die nichtenzymatische Cystein‐S‐Glykosylierung von verschiedenen Proteinen. Dieser künstliche Prozess hat großen Einfluss auf die metabolische Glykanmarkierung in lebenden Zellen, kann aber durch die Verwendung nichtacetylierter nichtnatürlicher Zucker umgangen werden. Mithilfe von GalNAz wurde eine korrigierte Liste O‐GlcNAcylierter Proteine und O‐GlcNAc‐Stellen in HeLa‐Zellen erstellt.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ange.201711710</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0002-3058-7370</orcidid></addata></record> |
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| subjects | Chemistry Chemoproteomik Cysteine Glycan Glycosylation Labeling Markierung Metabolism Monosaccharides Nichtnatürliche Monosaccharide O-GlcNAc Proteins S-Glykosylierungen Sugar |
| title | Artificial Cysteine S‐Glycosylation Induced by Per‐O‐Acetylated Unnatural Monosaccharides during Metabolic Glycan Labeling |
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