Expeditious oligosaccharide synthesis via selective, semi-orthogonal, and orthogonal activation
Traditional strategies for oligosaccharide synthesis often require extensive protecting and/or leaving group manipulations between each glycosylation step, thereby increasing the total number of synthetic steps while decreasing the efficiency of the synthesis. In contrast, expeditious strategies all...
Gespeichert in:
Veröffentlicht in: | Carbohydrate research 2011-09, Vol.346 (12), p.1371-1388 |
---|---|
Hauptverfasser: | , |
Format: | Artikel |
Sprache: | eng |
Schlagworte: | |
Online-Zugang: | Volltext |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
container_end_page | 1388 |
---|---|
container_issue | 12 |
container_start_page | 1371 |
container_title | Carbohydrate research |
container_volume | 346 |
creator | Kaeothip, Sophon Demchenko, Alexei V. |
description | Traditional strategies for oligosaccharide synthesis often require extensive protecting and/or leaving group manipulations between each glycosylation step, thereby increasing the total number of synthetic steps while decreasing the efficiency of the synthesis. In contrast, expeditious strategies allow for the rapid chemical synthesis of complex carbohydrates by minimizing extraneous chemical manipulations. Oligosaccharide synthesis by selective activation of one leaving group over another is one such expeditious strategy. Herein, the significant improvements that have recently emerged in the area of the selective activation are discussed. The development of orthogonal strategy further expands the scope of the selective activation methodology. Surveyed in this article, are representative examples wherein these excellent innovations have been applied to the synthesis of various oligosaccharide sequences. |
doi_str_mv | 10.1016/j.carres.2011.05.004 |
format | Article |
fullrecord | <record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_3129461</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0008621511002552</els_id><sourcerecordid>874896689</sourcerecordid><originalsourceid>FETCH-LOGICAL-c4674-6ea8ecd848d52035aab95ab674dcc3a38238b11534457fe3585ba94bd93be4453</originalsourceid><addsrcrecordid>eNp9kU1vEzEQhi0EoqHwDxDsjUt3sdcf670gVVX5kCpxgErcRrP2JHG0WQd7E9F_j6OUFi6c7PG88854HsZeC94ILsz7TeMwJcpNy4VouG44V0_YQthO1qo1P56yBefc1qYV-oy9yHlTQm4685ydtcIYaftuweD61458mEPc5yqOYRUzOrfGFDxV-W6a15RDrg4Bq0wjuTkc6KJct6GOaV7HVZxwvKhw8tVjXOFRh8V0esmeLXHM9Or-PGe3H6-_X32ub75--nJ1eVM7ZTpVG0JLzltlvW651IhDr3EoKe-cRGlbaQchtFRKd0uS2uoBezX4Xg5U3uQ5-3Dy3e2HLXlH05xwhF0KW0x3EDHAv5kprGEVDyBF2ysjisG7e4MUf-4pz7AN2dE44kRlN2A7ZXtjbF-U6qR0KeacaPnQRXA4ooENnNDAEQ1wDQVNKXvz94QPRX9YFMHbk2CJEXCVQobbb8XBHLkVo-7xk1Q2eQiUILtAkysAU0EDPob_z_Ab8rKuCw</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>874896689</pqid></control><display><type>article</type><title>Expeditious oligosaccharide synthesis via selective, semi-orthogonal, and orthogonal activation</title><source>MEDLINE</source><source>ScienceDirect Journals (5 years ago - present)</source><creator>Kaeothip, Sophon ; Demchenko, Alexei V.</creator><creatorcontrib>Kaeothip, Sophon ; Demchenko, Alexei V.</creatorcontrib><description>Traditional strategies for oligosaccharide synthesis often require extensive protecting and/or leaving group manipulations between each glycosylation step, thereby increasing the total number of synthetic steps while decreasing the efficiency of the synthesis. In contrast, expeditious strategies allow for the rapid chemical synthesis of complex carbohydrates by minimizing extraneous chemical manipulations. Oligosaccharide synthesis by selective activation of one leaving group over another is one such expeditious strategy. Herein, the significant improvements that have recently emerged in the area of the selective activation are discussed. The development of orthogonal strategy further expands the scope of the selective activation methodology. Surveyed in this article, are representative examples wherein these excellent innovations have been applied to the synthesis of various oligosaccharide sequences.</description><identifier>ISSN: 0008-6215</identifier><identifier>EISSN: 1873-426X</identifier><identifier>DOI: 10.1016/j.carres.2011.05.004</identifier><identifier>PMID: 21663897</identifier><language>eng</language><publisher>Netherlands: Elsevier Ltd</publisher><subject>Acetals - chemistry ; Acylation ; Carbohydrate Conformation ; Carbohydrate Sequence ; Chemistry, Organic - methods ; Fluorides - chemistry ; Glycomics ; Glycosides - chemical synthesis ; Glycosylation ; Halogens - chemistry ; Heparin - analogs & derivatives ; Heparin - chemical synthesis ; Imidoesters - chemistry ; Ionic Liquids - chemistry ; Molecular Sequence Data ; Oligosaccharides ; Oligosaccharides - chemical synthesis ; Orthogonality ; Selective activation ; Strategy ; Sulfoxides - chemistry ; synthesis ; Thiocyanates - chemistry</subject><ispartof>Carbohydrate research, 2011-09, Vol.346 (12), p.1371-1388</ispartof><rights>2011 Elsevier Ltd</rights><rights>Copyright © 2011 Elsevier Ltd. All rights reserved.</rights><rights>2011 Elsevier Science. All rights reserved. 2011</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4674-6ea8ecd848d52035aab95ab674dcc3a38238b11534457fe3585ba94bd93be4453</citedby><cites>FETCH-LOGICAL-c4674-6ea8ecd848d52035aab95ab674dcc3a38238b11534457fe3585ba94bd93be4453</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.2011.05.004$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>230,314,780,784,885,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21663897$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kaeothip, Sophon</creatorcontrib><creatorcontrib>Demchenko, Alexei V.</creatorcontrib><title>Expeditious oligosaccharide synthesis via selective, semi-orthogonal, and orthogonal activation</title><title>Carbohydrate research</title><addtitle>Carbohydr Res</addtitle><description>Traditional strategies for oligosaccharide synthesis often require extensive protecting and/or leaving group manipulations between each glycosylation step, thereby increasing the total number of synthetic steps while decreasing the efficiency of the synthesis. In contrast, expeditious strategies allow for the rapid chemical synthesis of complex carbohydrates by minimizing extraneous chemical manipulations. Oligosaccharide synthesis by selective activation of one leaving group over another is one such expeditious strategy. Herein, the significant improvements that have recently emerged in the area of the selective activation are discussed. The development of orthogonal strategy further expands the scope of the selective activation methodology. Surveyed in this article, are representative examples wherein these excellent innovations have been applied to the synthesis of various oligosaccharide sequences.</description><subject>Acetals - chemistry</subject><subject>Acylation</subject><subject>Carbohydrate Conformation</subject><subject>Carbohydrate Sequence</subject><subject>Chemistry, Organic - methods</subject><subject>Fluorides - chemistry</subject><subject>Glycomics</subject><subject>Glycosides - chemical synthesis</subject><subject>Glycosylation</subject><subject>Halogens - chemistry</subject><subject>Heparin - analogs & derivatives</subject><subject>Heparin - chemical synthesis</subject><subject>Imidoesters - chemistry</subject><subject>Ionic Liquids - chemistry</subject><subject>Molecular Sequence Data</subject><subject>Oligosaccharides</subject><subject>Oligosaccharides - chemical synthesis</subject><subject>Orthogonality</subject><subject>Selective activation</subject><subject>Strategy</subject><subject>Sulfoxides - chemistry</subject><subject>synthesis</subject><subject>Thiocyanates - chemistry</subject><issn>0008-6215</issn><issn>1873-426X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kU1vEzEQhi0EoqHwDxDsjUt3sdcf670gVVX5kCpxgErcRrP2JHG0WQd7E9F_j6OUFi6c7PG88854HsZeC94ILsz7TeMwJcpNy4VouG44V0_YQthO1qo1P56yBefc1qYV-oy9yHlTQm4685ydtcIYaftuweD61458mEPc5yqOYRUzOrfGFDxV-W6a15RDrg4Bq0wjuTkc6KJct6GOaV7HVZxwvKhw8tVjXOFRh8V0esmeLXHM9Or-PGe3H6-_X32ub75--nJ1eVM7ZTpVG0JLzltlvW651IhDr3EoKe-cRGlbaQchtFRKd0uS2uoBezX4Xg5U3uQ5-3Dy3e2HLXlH05xwhF0KW0x3EDHAv5kprGEVDyBF2ysjisG7e4MUf-4pz7AN2dE44kRlN2A7ZXtjbF-U6qR0KeacaPnQRXA4ooENnNDAEQ1wDQVNKXvz94QPRX9YFMHbk2CJEXCVQobbb8XBHLkVo-7xk1Q2eQiUILtAkysAU0EDPob_z_Ab8rKuCw</recordid><startdate>20110906</startdate><enddate>20110906</enddate><creator>Kaeothip, Sophon</creator><creator>Demchenko, Alexei V.</creator><general>Elsevier Ltd</general><scope>FBQ</scope><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><scope>5PM</scope></search><sort><creationdate>20110906</creationdate><title>Expeditious oligosaccharide synthesis via selective, semi-orthogonal, and orthogonal activation</title><author>Kaeothip, Sophon ; Demchenko, Alexei V.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4674-6ea8ecd848d52035aab95ab674dcc3a38238b11534457fe3585ba94bd93be4453</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Acetals - chemistry</topic><topic>Acylation</topic><topic>Carbohydrate Conformation</topic><topic>Carbohydrate Sequence</topic><topic>Chemistry, Organic - methods</topic><topic>Fluorides - chemistry</topic><topic>Glycomics</topic><topic>Glycosides - chemical synthesis</topic><topic>Glycosylation</topic><topic>Halogens - chemistry</topic><topic>Heparin - analogs & derivatives</topic><topic>Heparin - chemical synthesis</topic><topic>Imidoesters - chemistry</topic><topic>Ionic Liquids - chemistry</topic><topic>Molecular Sequence Data</topic><topic>Oligosaccharides</topic><topic>Oligosaccharides - chemical synthesis</topic><topic>Orthogonality</topic><topic>Selective activation</topic><topic>Strategy</topic><topic>Sulfoxides - chemistry</topic><topic>synthesis</topic><topic>Thiocyanates - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kaeothip, Sophon</creatorcontrib><creatorcontrib>Demchenko, Alexei V.</creatorcontrib><collection>AGRIS</collection><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><collection>PubMed Central (Full Participant titles)</collection><jtitle>Carbohydrate research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kaeothip, Sophon</au><au>Demchenko, Alexei V.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Expeditious oligosaccharide synthesis via selective, semi-orthogonal, and orthogonal activation</atitle><jtitle>Carbohydrate research</jtitle><addtitle>Carbohydr Res</addtitle><date>2011-09-06</date><risdate>2011</risdate><volume>346</volume><issue>12</issue><spage>1371</spage><epage>1388</epage><pages>1371-1388</pages><issn>0008-6215</issn><eissn>1873-426X</eissn><abstract>Traditional strategies for oligosaccharide synthesis often require extensive protecting and/or leaving group manipulations between each glycosylation step, thereby increasing the total number of synthetic steps while decreasing the efficiency of the synthesis. In contrast, expeditious strategies allow for the rapid chemical synthesis of complex carbohydrates by minimizing extraneous chemical manipulations. Oligosaccharide synthesis by selective activation of one leaving group over another is one such expeditious strategy. Herein, the significant improvements that have recently emerged in the area of the selective activation are discussed. The development of orthogonal strategy further expands the scope of the selective activation methodology. Surveyed in this article, are representative examples wherein these excellent innovations have been applied to the synthesis of various oligosaccharide sequences.</abstract><cop>Netherlands</cop><pub>Elsevier Ltd</pub><pmid>21663897</pmid><doi>10.1016/j.carres.2011.05.004</doi><tpages>18</tpages><oa>free_for_read</oa></addata></record> |
fulltext | fulltext |
identifier | ISSN: 0008-6215 |
ispartof | Carbohydrate research, 2011-09, Vol.346 (12), p.1371-1388 |
issn | 0008-6215 1873-426X |
language | eng |
recordid | cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_3129461 |
source | MEDLINE; ScienceDirect Journals (5 years ago - present) |
subjects | Acetals - chemistry Acylation Carbohydrate Conformation Carbohydrate Sequence Chemistry, Organic - methods Fluorides - chemistry Glycomics Glycosides - chemical synthesis Glycosylation Halogens - chemistry Heparin - analogs & derivatives Heparin - chemical synthesis Imidoesters - chemistry Ionic Liquids - chemistry Molecular Sequence Data Oligosaccharides Oligosaccharides - chemical synthesis Orthogonality Selective activation Strategy Sulfoxides - chemistry synthesis Thiocyanates - chemistry |
title | Expeditious oligosaccharide synthesis via selective, semi-orthogonal, and orthogonal activation |
url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-21T01%3A07%3A56IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_pubme&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Expeditious%20oligosaccharide%20synthesis%20via%20selective,%20semi-orthogonal,%20and%20orthogonal%20activation&rft.jtitle=Carbohydrate%20research&rft.au=Kaeothip,%20Sophon&rft.date=2011-09-06&rft.volume=346&rft.issue=12&rft.spage=1371&rft.epage=1388&rft.pages=1371-1388&rft.issn=0008-6215&rft.eissn=1873-426X&rft_id=info:doi/10.1016/j.carres.2011.05.004&rft_dat=%3Cproquest_pubme%3E874896689%3C/proquest_pubme%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=874896689&rft_id=info:pmid/21663897&rft_els_id=S0008621511002552&rfr_iscdi=true |