Synthesis and Evaluation of a New Fluorescent Transglycosylase Substrate: Lipid II-Based Molecule Possessing a Dansyl-C20 Polyprenyl Moiety
The preparation of a novel fluorescent lipid II-based substrate for transglycosylases (TGases) is described. This substrate has characteristic structural features including a shorter lipid chain, a fluorophore tag at the end of the lipid chain rather than on the peptide chain, and no labeling with a...
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| Veröffentlicht in: | Organic letters 2010-04, Vol.12 (7), p.1608-1611 |
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| container_title | Organic letters |
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| creator | Liu, Chen-Yu Guo, Chih-Wei Chang, Yi-Fan Wang, Jen-Tsung Shih, Hao-Wei Hsu, Yu-Fang Chen, Chia-Wei Chen, Shao-Kang Wang, Yen-Chih Cheng, Ting-Jen R Ma, Che Wong, Chi-Huey Fang, Jim-Min Cheng, Wei-Chieh |
| description | The preparation of a novel fluorescent lipid II-based substrate for transglycosylases (TGases) is described. This substrate has characteristic structural features including a shorter lipid chain, a fluorophore tag at the end of the lipid chain rather than on the peptide chain, and no labeling with a radioactive atom. This fluorescent substrate is readily utilized in TGase activity assays to characterize TGases and also to evaluate the activities of TGase inhibitors. |
| doi_str_mv | 10.1021/ol100338v |
| format | Article |
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This substrate has characteristic structural features including a shorter lipid chain, a fluorophore tag at the end of the lipid chain rather than on the peptide chain, and no labeling with a radioactive atom. This fluorescent substrate is readily utilized in TGase activity assays to characterize TGases and also to evaluate the activities of TGase inhibitors.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol100338v</identifier><identifier>PMID: 20187630</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Bambermycins - pharmacology ; Enzyme Inhibitors - pharmacology ; Fluorescence ; Glycosyltransferases - antagonists & inhibitors ; Glycosyltransferases - metabolism ; Molecular Structure ; Polyisoprenyl Phosphates - chemical synthesis ; Polyisoprenyl Phosphates - chemistry ; Polyisoprenyl Phosphates - metabolism ; Structure-Activity Relationship ; Substrate Specificity ; Uridine Diphosphate N-Acetylmuramic Acid - analogs & derivatives ; Uridine Diphosphate N-Acetylmuramic Acid - chemistry ; Uridine Diphosphate N-Acetylmuramic Acid - metabolism</subject><ispartof>Organic letters, 2010-04, Vol.12 (7), p.1608-1611</ispartof><rights>Copyright © 2010 American Chemical Society</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a415t-8cc9c1f8cb010d935605f42ee5a3077f6ee538c5f28753e86c7330cce89b32463</citedby><cites>FETCH-LOGICAL-a415t-8cc9c1f8cb010d935605f42ee5a3077f6ee538c5f28753e86c7330cce89b32463</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/ol100338v$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol100338v$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/20187630$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Liu, Chen-Yu</creatorcontrib><creatorcontrib>Guo, Chih-Wei</creatorcontrib><creatorcontrib>Chang, Yi-Fan</creatorcontrib><creatorcontrib>Wang, Jen-Tsung</creatorcontrib><creatorcontrib>Shih, Hao-Wei</creatorcontrib><creatorcontrib>Hsu, Yu-Fang</creatorcontrib><creatorcontrib>Chen, Chia-Wei</creatorcontrib><creatorcontrib>Chen, Shao-Kang</creatorcontrib><creatorcontrib>Wang, Yen-Chih</creatorcontrib><creatorcontrib>Cheng, Ting-Jen R</creatorcontrib><creatorcontrib>Ma, Che</creatorcontrib><creatorcontrib>Wong, Chi-Huey</creatorcontrib><creatorcontrib>Fang, Jim-Min</creatorcontrib><creatorcontrib>Cheng, Wei-Chieh</creatorcontrib><title>Synthesis and Evaluation of a New Fluorescent Transglycosylase Substrate: Lipid II-Based Molecule Possessing a Dansyl-C20 Polyprenyl Moiety</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>The preparation of a novel fluorescent lipid II-based substrate for transglycosylases (TGases) is described. This substrate has characteristic structural features including a shorter lipid chain, a fluorophore tag at the end of the lipid chain rather than on the peptide chain, and no labeling with a radioactive atom. This fluorescent substrate is readily utilized in TGase activity assays to characterize TGases and also to evaluate the activities of TGase inhibitors.</description><subject>Bambermycins - pharmacology</subject><subject>Enzyme Inhibitors - pharmacology</subject><subject>Fluorescence</subject><subject>Glycosyltransferases - antagonists & inhibitors</subject><subject>Glycosyltransferases - metabolism</subject><subject>Molecular Structure</subject><subject>Polyisoprenyl Phosphates - chemical synthesis</subject><subject>Polyisoprenyl Phosphates - chemistry</subject><subject>Polyisoprenyl Phosphates - metabolism</subject><subject>Structure-Activity Relationship</subject><subject>Substrate Specificity</subject><subject>Uridine Diphosphate N-Acetylmuramic Acid - analogs & derivatives</subject><subject>Uridine Diphosphate N-Acetylmuramic Acid - chemistry</subject><subject>Uridine Diphosphate N-Acetylmuramic Acid - metabolism</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkMtOwzAQRS0EolBY8APIG4RYBMZx8yg7KK9K5SEB68h1JiWVaxdPAso38NMYFbpiNVczZ650L2MHAk4FxOLMGQEgZf6xwXZEEssogyTeXOsUemyXaA4gwma4zXoxiDxLJeywr-fONm9INXFlS379oUyrmtpZ7iqu-AN-8hvTOo-k0Tb8xStLM9NpR51RhPy5nVLjVYPnfFIv65KPx9FlOJT83hnUrUH-5IiQqLazYHgV_jsTjWIIe9MtPdrOBLbGpttjW5UyhPu_s89eb65fRnfR5PF2PLqYRGogkibKtR5qUeV6CgLKoUxSSKpBjJgoCVlWpUHJXCdVnGeJxDzVmZSgNebDqYwHqeyz45Xv0rv3FqkpFnWIZ4yy6FoqAj4AmUkI5MmK1D6E8FgVS18vlO8KAcVP9cW6-sAe_rq20wWWa_Kv6wAcrQClqZi71tsQ8h-jbzWzi6M</recordid><startdate>20100402</startdate><enddate>20100402</enddate><creator>Liu, Chen-Yu</creator><creator>Guo, Chih-Wei</creator><creator>Chang, Yi-Fan</creator><creator>Wang, Jen-Tsung</creator><creator>Shih, Hao-Wei</creator><creator>Hsu, Yu-Fang</creator><creator>Chen, Chia-Wei</creator><creator>Chen, Shao-Kang</creator><creator>Wang, Yen-Chih</creator><creator>Cheng, Ting-Jen R</creator><creator>Ma, Che</creator><creator>Wong, Chi-Huey</creator><creator>Fang, Jim-Min</creator><creator>Cheng, Wei-Chieh</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20100402</creationdate><title>Synthesis and Evaluation of a New Fluorescent Transglycosylase Substrate: Lipid II-Based Molecule Possessing a Dansyl-C20 Polyprenyl Moiety</title><author>Liu, Chen-Yu ; Guo, Chih-Wei ; Chang, Yi-Fan ; Wang, Jen-Tsung ; Shih, Hao-Wei ; Hsu, Yu-Fang ; Chen, Chia-Wei ; Chen, Shao-Kang ; Wang, Yen-Chih ; Cheng, Ting-Jen R ; Ma, Che ; Wong, Chi-Huey ; Fang, Jim-Min ; Cheng, Wei-Chieh</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a415t-8cc9c1f8cb010d935605f42ee5a3077f6ee538c5f28753e86c7330cce89b32463</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>Bambermycins - pharmacology</topic><topic>Enzyme Inhibitors - pharmacology</topic><topic>Fluorescence</topic><topic>Glycosyltransferases - antagonists & inhibitors</topic><topic>Glycosyltransferases - metabolism</topic><topic>Molecular Structure</topic><topic>Polyisoprenyl Phosphates - chemical synthesis</topic><topic>Polyisoprenyl Phosphates - chemistry</topic><topic>Polyisoprenyl Phosphates - metabolism</topic><topic>Structure-Activity Relationship</topic><topic>Substrate Specificity</topic><topic>Uridine Diphosphate N-Acetylmuramic Acid - analogs & derivatives</topic><topic>Uridine Diphosphate N-Acetylmuramic Acid - chemistry</topic><topic>Uridine Diphosphate N-Acetylmuramic Acid - metabolism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Liu, Chen-Yu</creatorcontrib><creatorcontrib>Guo, Chih-Wei</creatorcontrib><creatorcontrib>Chang, Yi-Fan</creatorcontrib><creatorcontrib>Wang, Jen-Tsung</creatorcontrib><creatorcontrib>Shih, Hao-Wei</creatorcontrib><creatorcontrib>Hsu, Yu-Fang</creatorcontrib><creatorcontrib>Chen, Chia-Wei</creatorcontrib><creatorcontrib>Chen, Shao-Kang</creatorcontrib><creatorcontrib>Wang, Yen-Chih</creatorcontrib><creatorcontrib>Cheng, Ting-Jen R</creatorcontrib><creatorcontrib>Ma, Che</creatorcontrib><creatorcontrib>Wong, Chi-Huey</creatorcontrib><creatorcontrib>Fang, Jim-Min</creatorcontrib><creatorcontrib>Cheng, Wei-Chieh</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Liu, Chen-Yu</au><au>Guo, Chih-Wei</au><au>Chang, Yi-Fan</au><au>Wang, Jen-Tsung</au><au>Shih, Hao-Wei</au><au>Hsu, Yu-Fang</au><au>Chen, Chia-Wei</au><au>Chen, Shao-Kang</au><au>Wang, Yen-Chih</au><au>Cheng, Ting-Jen R</au><au>Ma, Che</au><au>Wong, Chi-Huey</au><au>Fang, Jim-Min</au><au>Cheng, Wei-Chieh</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Evaluation of a New Fluorescent Transglycosylase Substrate: Lipid II-Based Molecule Possessing a Dansyl-C20 Polyprenyl Moiety</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2010-04-02</date><risdate>2010</risdate><volume>12</volume><issue>7</issue><spage>1608</spage><epage>1611</epage><pages>1608-1611</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>The preparation of a novel fluorescent lipid II-based substrate for transglycosylases (TGases) is described. This substrate has characteristic structural features including a shorter lipid chain, a fluorophore tag at the end of the lipid chain rather than on the peptide chain, and no labeling with a radioactive atom. This fluorescent substrate is readily utilized in TGase activity assays to characterize TGases and also to evaluate the activities of TGase inhibitors.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>20187630</pmid><doi>10.1021/ol100338v</doi><tpages>4</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Organic letters, 2010-04, Vol.12 (7), p.1608-1611 |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Bambermycins - pharmacology Enzyme Inhibitors - pharmacology Fluorescence Glycosyltransferases - antagonists & inhibitors Glycosyltransferases - metabolism Molecular Structure Polyisoprenyl Phosphates - chemical synthesis Polyisoprenyl Phosphates - chemistry Polyisoprenyl Phosphates - metabolism Structure-Activity Relationship Substrate Specificity Uridine Diphosphate N-Acetylmuramic Acid - analogs & derivatives Uridine Diphosphate N-Acetylmuramic Acid - chemistry Uridine Diphosphate N-Acetylmuramic Acid - metabolism |
| title | Synthesis and Evaluation of a New Fluorescent Transglycosylase Substrate: Lipid II-Based Molecule Possessing a Dansyl-C20 Polyprenyl Moiety |
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