Common side reactions of the glycosyl donor in chemical glycosylation
Chemical glycosylation is central to carbohydrate chemistry and is generally recognised as a challenging reaction. This review describes the most reoccurring side reactions of glycosyl donors in glycosylation and how scientists have attempted to explain their observations and in some cases succeeded...
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| Veröffentlicht in: | Carbohydrate research 2015-05, Vol.408, p.51-95 |
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| container_title | Carbohydrate research |
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| creator | Christensen, Helle M. Oscarson, Stefan Jensen, Henrik H. |
| description | Chemical glycosylation is central to carbohydrate chemistry and is generally recognised as a challenging reaction. This review describes the most reoccurring side reactions of glycosyl donors in glycosylation and how scientists have attempted to explain their observations and in some cases succeeded in solving a particular encountered problem. The topics covered are donor hydrolysis, elimination to form glycals, intermolecular aglycon transfer of thioglycosides and glycosyl imidate rearrangement.
[Display omitted]
•Glycosyl donor hydrolysis is discussed.•Glycosyl donors may undergo elimination reactions in competition with substitution.•The sulfur atom of thioglycosides may act as a nucleophile in glycosylation.•Glycosyl trichloroacetimidates can undergo rearrangement to amides. |
| doi_str_mv | 10.1016/j.carres.2015.02.007 |
| format | Article |
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[Display omitted]
•Glycosyl donor hydrolysis is discussed.•Glycosyl donors may undergo elimination reactions in competition with substitution.•The sulfur atom of thioglycosides may act as a nucleophile in glycosylation.•Glycosyl trichloroacetimidates can undergo rearrangement to amides.</description><identifier>ISSN: 0008-6215</identifier><identifier>EISSN: 1873-426X</identifier><identifier>DOI: 10.1016/j.carres.2015.02.007</identifier><identifier>PMID: 25862946</identifier><language>eng</language><publisher>Netherlands: Elsevier Ltd</publisher><subject>By-products ; Elimination ; Glycosylation ; Hydrolysis ; Molecular Structure ; Thioglycosides ; Thioglycosides - chemistry ; Trichloroacetimidates</subject><ispartof>Carbohydrate research, 2015-05, Vol.408, p.51-95</ispartof><rights>2015 Elsevier Ltd</rights><rights>Copyright © 2015 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c428t-79e516a747850d51eacd3a5b51c74f838c5517b6567b2267fc697af99ed202303</citedby><cites>FETCH-LOGICAL-c428t-79e516a747850d51eacd3a5b51c74f838c5517b6567b2267fc697af99ed202303</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.carres.2015.02.007$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>315,781,785,3551,27929,27930,46000</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25862946$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Christensen, Helle M.</creatorcontrib><creatorcontrib>Oscarson, Stefan</creatorcontrib><creatorcontrib>Jensen, Henrik H.</creatorcontrib><title>Common side reactions of the glycosyl donor in chemical glycosylation</title><title>Carbohydrate research</title><addtitle>Carbohydr Res</addtitle><description>Chemical glycosylation is central to carbohydrate chemistry and is generally recognised as a challenging reaction. This review describes the most reoccurring side reactions of glycosyl donors in glycosylation and how scientists have attempted to explain their observations and in some cases succeeded in solving a particular encountered problem. The topics covered are donor hydrolysis, elimination to form glycals, intermolecular aglycon transfer of thioglycosides and glycosyl imidate rearrangement.
[Display omitted]
•Glycosyl donor hydrolysis is discussed.•Glycosyl donors may undergo elimination reactions in competition with substitution.•The sulfur atom of thioglycosides may act as a nucleophile in glycosylation.•Glycosyl trichloroacetimidates can undergo rearrangement to amides.</description><subject>By-products</subject><subject>Elimination</subject><subject>Glycosylation</subject><subject>Hydrolysis</subject><subject>Molecular Structure</subject><subject>Thioglycosides</subject><subject>Thioglycosides - chemistry</subject><subject>Trichloroacetimidates</subject><issn>0008-6215</issn><issn>1873-426X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kF1LwzAUhoMobk7_gUgvvWk9SfPR3ggy5gcMvFHwLqTpqctom5l0wv69HZteehUOed7zch5CrilkFKi8W2fWhIAxY0BFBiwDUCdkSguVp5zJj1MyBYAilYyKCbmIcT2OIJU8JxMmCslKLqdkMfdd5_skuhqTgMYOzvcx8U0yrDD5bHfWx12b1L73IXF9YlfYOWvavy-zD1ySs8a0Ea-O74y8Py7e5s_p8vXpZf6wTC1nxZCqEgWVRnFVCKgFHevq3IhKUKt4U-SFFYKqSgqpKsakaqwslWnKEmsGLId8Rm4PezfBf20xDrpz0WLbmh79NmoqS66AQ5mPKD-gNvgYAzZ6E1xnwk5T0HuBeq0PAvVeoAamR4Fj7ObYsK06rP9Cv8ZG4P4A4Hjnt8Ogo3XYW6xdQDvo2rv_G34AktqC8Q</recordid><startdate>20150518</startdate><enddate>20150518</enddate><creator>Christensen, Helle M.</creator><creator>Oscarson, Stefan</creator><creator>Jensen, Henrik H.</creator><general>Elsevier Ltd</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>20150518</creationdate><title>Common side reactions of the glycosyl donor in chemical glycosylation</title><author>Christensen, Helle M. ; Oscarson, Stefan ; Jensen, Henrik H.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c428t-79e516a747850d51eacd3a5b51c74f838c5517b6567b2267fc697af99ed202303</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>By-products</topic><topic>Elimination</topic><topic>Glycosylation</topic><topic>Hydrolysis</topic><topic>Molecular Structure</topic><topic>Thioglycosides</topic><topic>Thioglycosides - chemistry</topic><topic>Trichloroacetimidates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Christensen, Helle M.</creatorcontrib><creatorcontrib>Oscarson, Stefan</creatorcontrib><creatorcontrib>Jensen, Henrik H.</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>Carbohydrate research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Christensen, Helle M.</au><au>Oscarson, Stefan</au><au>Jensen, Henrik H.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Common side reactions of the glycosyl donor in chemical glycosylation</atitle><jtitle>Carbohydrate research</jtitle><addtitle>Carbohydr Res</addtitle><date>2015-05-18</date><risdate>2015</risdate><volume>408</volume><spage>51</spage><epage>95</epage><pages>51-95</pages><issn>0008-6215</issn><eissn>1873-426X</eissn><abstract>Chemical glycosylation is central to carbohydrate chemistry and is generally recognised as a challenging reaction. This review describes the most reoccurring side reactions of glycosyl donors in glycosylation and how scientists have attempted to explain their observations and in some cases succeeded in solving a particular encountered problem. The topics covered are donor hydrolysis, elimination to form glycals, intermolecular aglycon transfer of thioglycosides and glycosyl imidate rearrangement.
[Display omitted]
•Glycosyl donor hydrolysis is discussed.•Glycosyl donors may undergo elimination reactions in competition with substitution.•The sulfur atom of thioglycosides may act as a nucleophile in glycosylation.•Glycosyl trichloroacetimidates can undergo rearrangement to amides.</abstract><cop>Netherlands</cop><pub>Elsevier Ltd</pub><pmid>25862946</pmid><doi>10.1016/j.carres.2015.02.007</doi><tpages>45</tpages></addata></record> |
| fulltext | fulltext |
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| ispartof | Carbohydrate research, 2015-05, Vol.408, p.51-95 |
| issn | 0008-6215 1873-426X |
| language | eng |
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| source | MEDLINE; Access via ScienceDirect (Elsevier) |
| subjects | By-products Elimination Glycosylation Hydrolysis Molecular Structure Thioglycosides Thioglycosides - chemistry Trichloroacetimidates |
| title | Common side reactions of the glycosyl donor in chemical glycosylation |
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