Direct aqueous synthesis of cyanomethyl thioglycosides from reducing sugars; ready access to reagents for protein glycosylation
Unprotected carbohydrates can be directly converted into cyanomethyl thioglycosides in a completely stereoselective manner by reaction with 2-chloro-1,3-dimethylimidazolinium chloride (DMC) and mercaptoacetonitrile in aqueous solution in the presence of triethylamine. Reaction with methoxide provide...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2016-01, Vol.14 (28), p.6679-6682 |
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| container_title | Organic & biomolecular chemistry |
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| creator | Alexander, Stewart R Fairbanks, Antony J |
| description | Unprotected carbohydrates can be directly converted into cyanomethyl thioglycosides in a completely stereoselective manner by reaction with 2-chloro-1,3-dimethylimidazolinium chloride (DMC) and mercaptoacetonitrile in aqueous solution in the presence of triethylamine. Reaction with methoxide provides 2-imino-2-methoxyethyl (IME) thioglycosides, which may be used directly for the glycosylation of surface protein lysine residues.
Unprotected carbohydrates can be directly converted into cyanooethyl thioglycosides, which in turn may be used for protein glycosylation, in a completely stereoselective manner by reaction with 2-chloro-1,3-dimethylimidazolinium chloride (DMC) and mercaptoacetonitrile in aqueous solution. |
| doi_str_mv | 10.1039/c6ob01069e |
| format | Article |
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Unprotected carbohydrates can be directly converted into cyanooethyl thioglycosides, which in turn may be used for protein glycosylation, in a completely stereoselective manner by reaction with 2-chloro-1,3-dimethylimidazolinium chloride (DMC) and mercaptoacetonitrile in aqueous solution.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/c6ob01069e</identifier><identifier>PMID: 27327112</identifier><language>eng</language><publisher>England</publisher><subject>Animals ; Chickens ; Glycosylation ; Halogenation ; Indicators and Reagents - chemical synthesis ; Indicators and Reagents - chemistry ; Lysine - chemistry ; Methylation ; Models, Molecular ; Muramidase - chemistry ; Nitriles - chemical synthesis ; Nitriles - chemistry ; Oligosaccharides - chemical synthesis ; Oligosaccharides - chemistry ; Oxidation-Reduction ; Proteins - chemistry ; Thioglycosides - chemical synthesis ; Thioglycosides - chemistry</subject><ispartof>Organic & biomolecular chemistry, 2016-01, Vol.14 (28), p.6679-6682</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c342t-b32825a5ec693fc6de0f7dddcae368b3015a0753d50e5fef1bdb8ec893b39fcb3</citedby><cites>FETCH-LOGICAL-c342t-b32825a5ec693fc6de0f7dddcae368b3015a0753d50e5fef1bdb8ec893b39fcb3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/27327112$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Alexander, Stewart R</creatorcontrib><creatorcontrib>Fairbanks, Antony J</creatorcontrib><title>Direct aqueous synthesis of cyanomethyl thioglycosides from reducing sugars; ready access to reagents for protein glycosylation</title><title>Organic & biomolecular chemistry</title><addtitle>Org Biomol Chem</addtitle><description>Unprotected carbohydrates can be directly converted into cyanomethyl thioglycosides in a completely stereoselective manner by reaction with 2-chloro-1,3-dimethylimidazolinium chloride (DMC) and mercaptoacetonitrile in aqueous solution in the presence of triethylamine. Reaction with methoxide provides 2-imino-2-methoxyethyl (IME) thioglycosides, which may be used directly for the glycosylation of surface protein lysine residues.
Unprotected carbohydrates can be directly converted into cyanooethyl thioglycosides, which in turn may be used for protein glycosylation, in a completely stereoselective manner by reaction with 2-chloro-1,3-dimethylimidazolinium chloride (DMC) and mercaptoacetonitrile in aqueous solution.</description><subject>Animals</subject><subject>Chickens</subject><subject>Glycosylation</subject><subject>Halogenation</subject><subject>Indicators and Reagents - chemical synthesis</subject><subject>Indicators and Reagents - chemistry</subject><subject>Lysine - chemistry</subject><subject>Methylation</subject><subject>Models, Molecular</subject><subject>Muramidase - chemistry</subject><subject>Nitriles - chemical synthesis</subject><subject>Nitriles - chemistry</subject><subject>Oligosaccharides - chemical synthesis</subject><subject>Oligosaccharides - chemistry</subject><subject>Oxidation-Reduction</subject><subject>Proteins - chemistry</subject><subject>Thioglycosides - chemical synthesis</subject><subject>Thioglycosides - chemistry</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkTtPwzAURi0EolBY2EGekQJ23LzEBKU8pEpdYI4c-zo1SuPi6wyZ-OukBMp0X0ffcC4hF5zdcCaKW5W6inGWFnBATvgsyyKWiOJw38dsQk4RPxjjRZbOjskkzkSccR6fkK9H60EFKj87cB1S7NuwBrRInaGql63bQFj3DQ1r6-qmVw6tBqTGuw31oDtl25piV0uPd8NC6p5KpQCRBreba2jDgDtPt94FsC0dU_pGBuvaM3JkZINw_lun5P1p8TZ_iZar59f5_TJSYhaHqBJxHicyAZUWwqhUAzOZ1lpJEGleCcYTybJE6IRBYsDwSlc5qLwQlSiMqsSUXI-5yjtED6bceruRvi85K3cWy3m6evixuBjgqxHedtUG9B790zYAlyPgUe2v_28Q39J5fBY</recordid><startdate>20160101</startdate><enddate>20160101</enddate><creator>Alexander, Stewart R</creator><creator>Fairbanks, Antony J</creator><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20160101</creationdate><title>Direct aqueous synthesis of cyanomethyl thioglycosides from reducing sugars; ready access to reagents for protein glycosylation</title><author>Alexander, Stewart R ; Fairbanks, Antony J</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c342t-b32825a5ec693fc6de0f7dddcae368b3015a0753d50e5fef1bdb8ec893b39fcb3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Animals</topic><topic>Chickens</topic><topic>Glycosylation</topic><topic>Halogenation</topic><topic>Indicators and Reagents - chemical synthesis</topic><topic>Indicators and Reagents - chemistry</topic><topic>Lysine - chemistry</topic><topic>Methylation</topic><topic>Models, Molecular</topic><topic>Muramidase - chemistry</topic><topic>Nitriles - chemical synthesis</topic><topic>Nitriles - chemistry</topic><topic>Oligosaccharides - chemical synthesis</topic><topic>Oligosaccharides - chemistry</topic><topic>Oxidation-Reduction</topic><topic>Proteins - chemistry</topic><topic>Thioglycosides - chemical synthesis</topic><topic>Thioglycosides - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Alexander, Stewart R</creatorcontrib><creatorcontrib>Fairbanks, Antony J</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Alexander, Stewart R</au><au>Fairbanks, Antony J</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Direct aqueous synthesis of cyanomethyl thioglycosides from reducing sugars; ready access to reagents for protein glycosylation</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2016-01-01</date><risdate>2016</risdate><volume>14</volume><issue>28</issue><spage>6679</spage><epage>6682</epage><pages>6679-6682</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>Unprotected carbohydrates can be directly converted into cyanomethyl thioglycosides in a completely stereoselective manner by reaction with 2-chloro-1,3-dimethylimidazolinium chloride (DMC) and mercaptoacetonitrile in aqueous solution in the presence of triethylamine. Reaction with methoxide provides 2-imino-2-methoxyethyl (IME) thioglycosides, which may be used directly for the glycosylation of surface protein lysine residues.
Unprotected carbohydrates can be directly converted into cyanooethyl thioglycosides, which in turn may be used for protein glycosylation, in a completely stereoselective manner by reaction with 2-chloro-1,3-dimethylimidazolinium chloride (DMC) and mercaptoacetonitrile in aqueous solution.</abstract><cop>England</cop><pmid>27327112</pmid><doi>10.1039/c6ob01069e</doi><tpages>4</tpages></addata></record> |
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| ispartof | Organic & biomolecular chemistry, 2016-01, Vol.14 (28), p.6679-6682 |
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| source | MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Animals Chickens Glycosylation Halogenation Indicators and Reagents - chemical synthesis Indicators and Reagents - chemistry Lysine - chemistry Methylation Models, Molecular Muramidase - chemistry Nitriles - chemical synthesis Nitriles - chemistry Oligosaccharides - chemical synthesis Oligosaccharides - chemistry Oxidation-Reduction Proteins - chemistry Thioglycosides - chemical synthesis Thioglycosides - chemistry |
| title | Direct aqueous synthesis of cyanomethyl thioglycosides from reducing sugars; ready access to reagents for protein glycosylation |
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