Chemical Synthesis of Glycosaminoglycans
Glycosaminoglycans (GAGs) as one major part of the glycocalyx are involved in many essential biological cell processes, as well as in many courses of diseases. Because of the potential therapeutic application of GAG polymers, fragments, and also derivatives toward different diseases (e.g., heparin d...
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| Veröffentlicht in: | Chemical reviews 2016-07, Vol.116 (14), p.8193-8255 |
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| container_title | Chemical reviews |
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| creator | Mende, Marco Bednarek, Christin Wawryszyn, Mirella Sauter, Paul Biskup, Moritz B Schepers, Ute Bräse, Stefan |
| description | Glycosaminoglycans (GAGs) as one major part of the glycocalyx are involved in many essential biological cell processes, as well as in many courses of diseases. Because of the potential therapeutic application of GAG polymers, fragments, and also derivatives toward different diseases (e.g., heparin derivatives against Alzheimer’s disease), there is a continual growing demand for new chemical syntheses, which suffice the high claim to stereoselectivity and chemoselectivity. This Review summarizes the progress of chemical syntheses of GAGs over the last 10 years. For each class of the glycosaminoglycanshyaluronan (HA), heparan sulfate/heparin (HS/HP), chondroitin/dermatan sulfate (CS/DS), and keratan sulfate (KS)mainly novel glycosylation strategies, elongation sequences, and protecting group patterns are discussed, but also (semi)automated syntheses, enzymatic approaches, and functionalizations of synthesized or isolated GAGs are considered. |
| doi_str_mv | 10.1021/acs.chemrev.6b00010 |
| format | Article |
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For each class of the glycosaminoglycanshyaluronan (HA), heparan sulfate/heparin (HS/HP), chondroitin/dermatan sulfate (CS/DS), and keratan sulfate (KS)mainly novel glycosylation strategies, elongation sequences, and protecting group patterns are discussed, but also (semi)automated syntheses, enzymatic approaches, and functionalizations of synthesized or isolated GAGs are considered.</description><subject>Chemical synthesis</subject><subject>Combinatorial Chemistry Techniques</subject><subject>Disaccharides - chemistry</subject><subject>Enzymes</subject><subject>Glycosaminoglycans - chemical synthesis</subject><subject>Glycosaminoglycans - chemistry</subject><subject>Glycosylation</subject><subject>Monosaccharides - chemistry</subject><subject>Polymers</subject><issn>0009-2665</issn><issn>1520-6890</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kE1LAzEURYMotlZ_gSADbtxM-5JMvpZStAoFF-o6JJmMnTIfNWmF_ntTOurO1csL954HB6FrDFMMBM-Mi1O38m3wX1NuAQDDCRpjRiDnUsEpGqc_lRPO2QhdxLhOK2NEnKMREUVC8GKM7uaJUDvTZK_7brvysY5ZX2WLZu_6aNq66z_S03TxEp1Vpon-apgT9P748DZ_ypcvi-f5_TI3VNBtroi1Ba0IVdYJLksgwkpnSWEwGGU9YKYcF4WgVmHvFZMl4eBISYnFUlZ0gm6P3E3oP3c-bvW634UundRYFlgxRQCnFD2mXOhjDL7Sm1C3Juw1Bn2wo5MdPdjRg53UuhnYO9v68rfzoyMFZsfAof139x_kN8gycXM</recordid><startdate>20160727</startdate><enddate>20160727</enddate><creator>Mende, Marco</creator><creator>Bednarek, Christin</creator><creator>Wawryszyn, Mirella</creator><creator>Sauter, Paul</creator><creator>Biskup, Moritz B</creator><creator>Schepers, Ute</creator><creator>Bräse, Stefan</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>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20160727</creationdate><title>Chemical Synthesis of Glycosaminoglycans</title><author>Mende, Marco ; Bednarek, Christin ; Wawryszyn, Mirella ; Sauter, Paul ; Biskup, Moritz B ; Schepers, Ute ; Bräse, Stefan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a373t-92bb43f239bc768d027b8cb24a10a9be0159c67473b91ee958d260c2d32b188f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Chemical synthesis</topic><topic>Combinatorial Chemistry Techniques</topic><topic>Disaccharides - chemistry</topic><topic>Enzymes</topic><topic>Glycosaminoglycans - chemical synthesis</topic><topic>Glycosaminoglycans - chemistry</topic><topic>Glycosylation</topic><topic>Monosaccharides - chemistry</topic><topic>Polymers</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mende, Marco</creatorcontrib><creatorcontrib>Bednarek, Christin</creatorcontrib><creatorcontrib>Wawryszyn, Mirella</creatorcontrib><creatorcontrib>Sauter, Paul</creatorcontrib><creatorcontrib>Biskup, Moritz B</creatorcontrib><creatorcontrib>Schepers, Ute</creatorcontrib><creatorcontrib>Bräse, Stefan</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Chemical reviews</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Mende, Marco</au><au>Bednarek, Christin</au><au>Wawryszyn, Mirella</au><au>Sauter, Paul</au><au>Biskup, Moritz B</au><au>Schepers, Ute</au><au>Bräse, Stefan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Chemical Synthesis of Glycosaminoglycans</atitle><jtitle>Chemical reviews</jtitle><addtitle>Chem. 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| ispartof | Chemical reviews, 2016-07, Vol.116 (14), p.8193-8255 |
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| language | eng |
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| source | MEDLINE; ACS Publications |
| subjects | Chemical synthesis Combinatorial Chemistry Techniques Disaccharides - chemistry Enzymes Glycosaminoglycans - chemical synthesis Glycosaminoglycans - chemistry Glycosylation Monosaccharides - chemistry Polymers |
| title | Chemical Synthesis of Glycosaminoglycans |
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