Highly Efficient Synthesis of Monodisperse Poly(ethylene glycols) and Derivatives through Macrocyclization of Oligo(ethylene glycols)
A macrocyclic sulfate (MCS)‐based approach to monodisperse poly(ethylene glycols) (M‐PEGs) and their monofunctionalized derivatives has been developed. Macrocyclization of oligo(ethylene glycols) (OEGs) provides MCS (up to a 62‐membered macrocycle) as versatile precursors for a range of monofunction...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2015-03, Vol.54 (12), p.3763-3767 |
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| creator | Zhang, Hua Li, Xuefei Shi, Qiuyan Li, Yu Xia, Guiquan Chen, Long Yang, Zhigang Jiang, Zhong-Xing |
| description | A macrocyclic sulfate (MCS)‐based approach to monodisperse poly(ethylene glycols) (M‐PEGs) and their monofunctionalized derivatives has been developed. Macrocyclization of oligo(ethylene glycols) (OEGs) provides MCS (up to a 62‐membered macrocycle) as versatile precursors for a range of monofunctionalized M‐PEGs. Through iterative nucleophilic ring‐opening reactions of MCS without performing group protection and activation, a series of M‐PEGs, including the unprecedented 64‐mer (2850 Da), can be readily prepared. Synthetic simplicity coupled with versatility of this new strategy may pave the way for broader applications of M‐PEGs.
Macrocycles make synthesis easier: Convenient macrocyclization of the OEGs provides versatile macrocyclic sulfates. These compounds are cornerstones for both monofunctionalization of OEGs and highly efficient synthesis of monodisperse PEGs and derivatives, including an unprecedented 64‐mer. |
| doi_str_mv | 10.1002/anie.201410309 |
| format | Article |
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Macrocycles make synthesis easier: Convenient macrocyclization of the OEGs provides versatile macrocyclic sulfates. These compounds are cornerstones for both monofunctionalization of OEGs and highly efficient synthesis of monodisperse PEGs and derivatives, including an unprecedented 64‐mer.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201410309</identifier><identifier>PMID: 25655646</identifier><identifier>CODEN: ACIEAY</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Activation ; Chemical industry ; Crystallography, X-Ray ; Cyclization ; Derivatives ; Ethylene Glycols - chemistry ; Glycols ; Joining ; Joint ventures ; macrocycles ; Macrocyclic compounds ; macrocyclic sulfates ; Magnetic Resonance Spectroscopy ; Molecular Conformation ; poly(ethylene glycol) ; Polyethylene Glycols - chemical synthesis ; Polyethylene Glycols - chemistry ; Precursors ; Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization ; Strategy ; Sulfates ; Synthesis ; synthetic methods</subject><ispartof>Angewandte Chemie International Edition, 2015-03, Vol.54 (12), p.3763-3767</ispartof><rights>2015 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c6179-14f88d3d62651a7d4b4050415dc902327b988704ce93bc32cfa515ef7f0036bd3</citedby><cites>FETCH-LOGICAL-c6179-14f88d3d62651a7d4b4050415dc902327b988704ce93bc32cfa515ef7f0036bd3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fanie.201410309$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201410309$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1416,27923,27924,45573,45574</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25655646$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zhang, Hua</creatorcontrib><creatorcontrib>Li, Xuefei</creatorcontrib><creatorcontrib>Shi, Qiuyan</creatorcontrib><creatorcontrib>Li, Yu</creatorcontrib><creatorcontrib>Xia, Guiquan</creatorcontrib><creatorcontrib>Chen, Long</creatorcontrib><creatorcontrib>Yang, Zhigang</creatorcontrib><creatorcontrib>Jiang, Zhong-Xing</creatorcontrib><title>Highly Efficient Synthesis of Monodisperse Poly(ethylene glycols) and Derivatives through Macrocyclization of Oligo(ethylene glycols)</title><title>Angewandte Chemie International Edition</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>A macrocyclic sulfate (MCS)‐based approach to monodisperse poly(ethylene glycols) (M‐PEGs) and their monofunctionalized derivatives has been developed. Macrocyclization of oligo(ethylene glycols) (OEGs) provides MCS (up to a 62‐membered macrocycle) as versatile precursors for a range of monofunctionalized M‐PEGs. Through iterative nucleophilic ring‐opening reactions of MCS without performing group protection and activation, a series of M‐PEGs, including the unprecedented 64‐mer (2850 Da), can be readily prepared. Synthetic simplicity coupled with versatility of this new strategy may pave the way for broader applications of M‐PEGs.
Macrocycles make synthesis easier: Convenient macrocyclization of the OEGs provides versatile macrocyclic sulfates. These compounds are cornerstones for both monofunctionalization of OEGs and highly efficient synthesis of monodisperse PEGs and derivatives, including an unprecedented 64‐mer.</description><subject>Activation</subject><subject>Chemical industry</subject><subject>Crystallography, X-Ray</subject><subject>Cyclization</subject><subject>Derivatives</subject><subject>Ethylene Glycols - chemistry</subject><subject>Glycols</subject><subject>Joining</subject><subject>Joint ventures</subject><subject>macrocycles</subject><subject>Macrocyclic compounds</subject><subject>macrocyclic sulfates</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Molecular Conformation</subject><subject>poly(ethylene glycol)</subject><subject>Polyethylene Glycols - chemical synthesis</subject><subject>Polyethylene Glycols - chemistry</subject><subject>Precursors</subject><subject>Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization</subject><subject>Strategy</subject><subject>Sulfates</subject><subject>Synthesis</subject><subject>synthetic methods</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkc9v0zAYhiMEYmNw5YgscRmHFDv-lRynrqyTug2JISQuluN8aT3cuLOTsezO_42rjgrBYSd_kp_30We_WfaW4AnBuPioOwuTAhNGMMXVs-yQ8ILkVEr6PM2M0lyWnBxkr2K8SXxZYvEyOyi44FwwcZj9mtvlyo1o1rbWWOh69GXs-hVEG5Fv0YXvfGPjBkIE9Nm78Rj61eigA7R0o_EufkC6a9ApBHune3sHEfWr4IflCl1oE7wZjbMP6cZ3W9-Vs0v_v-N19qLVLsKbx_Mo-_ppdj2d54urs_PpySI3gsgqJ6wty4Y2ohCcaNmwmmGOGeGNqXBBC1lXZSkxM1DR2tDCtJoTDq1sMaaibuhRdrzzboK_HSD2am2jAed0B36IikhMcEUorZ5GRdqCVsmf0Pf_oDd-CF16yJYivGSswIma7Kj0KzEGaNUm2LUOoyJYbbtU2y7VvssUePeoHeo1NHv8T3kJqHbAT-tgfEKnTi7PZ3_L813Wxh7u91kdfighqeTq2-WZmuLFd764PlVz-ht907rK</recordid><startdate>20150316</startdate><enddate>20150316</enddate><creator>Zhang, Hua</creator><creator>Li, Xuefei</creator><creator>Shi, Qiuyan</creator><creator>Li, Yu</creator><creator>Xia, Guiquan</creator><creator>Chen, Long</creator><creator>Yang, Zhigang</creator><creator>Jiang, Zhong-Xing</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</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>7TM</scope><scope>K9.</scope><scope>7X8</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20150316</creationdate><title>Highly Efficient Synthesis of Monodisperse Poly(ethylene glycols) and Derivatives through Macrocyclization of Oligo(ethylene glycols)</title><author>Zhang, Hua ; Li, Xuefei ; Shi, Qiuyan ; Li, Yu ; Xia, Guiquan ; Chen, Long ; Yang, Zhigang ; Jiang, Zhong-Xing</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c6179-14f88d3d62651a7d4b4050415dc902327b988704ce93bc32cfa515ef7f0036bd3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Activation</topic><topic>Chemical industry</topic><topic>Crystallography, X-Ray</topic><topic>Cyclization</topic><topic>Derivatives</topic><topic>Ethylene Glycols - chemistry</topic><topic>Glycols</topic><topic>Joining</topic><topic>Joint ventures</topic><topic>macrocycles</topic><topic>Macrocyclic compounds</topic><topic>macrocyclic sulfates</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Molecular Conformation</topic><topic>poly(ethylene glycol)</topic><topic>Polyethylene Glycols - chemical synthesis</topic><topic>Polyethylene Glycols - chemistry</topic><topic>Precursors</topic><topic>Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization</topic><topic>Strategy</topic><topic>Sulfates</topic><topic>Synthesis</topic><topic>synthetic methods</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhang, Hua</creatorcontrib><creatorcontrib>Li, Xuefei</creatorcontrib><creatorcontrib>Shi, Qiuyan</creatorcontrib><creatorcontrib>Li, Yu</creatorcontrib><creatorcontrib>Xia, Guiquan</creatorcontrib><creatorcontrib>Chen, Long</creatorcontrib><creatorcontrib>Yang, Zhigang</creatorcontrib><creatorcontrib>Jiang, Zhong-Xing</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhang, Hua</au><au>Li, Xuefei</au><au>Shi, Qiuyan</au><au>Li, Yu</au><au>Xia, Guiquan</au><au>Chen, Long</au><au>Yang, Zhigang</au><au>Jiang, Zhong-Xing</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Highly Efficient Synthesis of Monodisperse Poly(ethylene glycols) and Derivatives through Macrocyclization of Oligo(ethylene glycols)</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew. Chem. Int. Ed</addtitle><date>2015-03-16</date><risdate>2015</risdate><volume>54</volume><issue>12</issue><spage>3763</spage><epage>3767</epage><pages>3763-3767</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><coden>ACIEAY</coden><abstract>A macrocyclic sulfate (MCS)‐based approach to monodisperse poly(ethylene glycols) (M‐PEGs) and their monofunctionalized derivatives has been developed. Macrocyclization of oligo(ethylene glycols) (OEGs) provides MCS (up to a 62‐membered macrocycle) as versatile precursors for a range of monofunctionalized M‐PEGs. Through iterative nucleophilic ring‐opening reactions of MCS without performing group protection and activation, a series of M‐PEGs, including the unprecedented 64‐mer (2850 Da), can be readily prepared. Synthetic simplicity coupled with versatility of this new strategy may pave the way for broader applications of M‐PEGs.
Macrocycles make synthesis easier: Convenient macrocyclization of the OEGs provides versatile macrocyclic sulfates. These compounds are cornerstones for both monofunctionalization of OEGs and highly efficient synthesis of monodisperse PEGs and derivatives, including an unprecedented 64‐mer.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>25655646</pmid><doi>10.1002/anie.201410309</doi><tpages>5</tpages><edition>International ed. in English</edition></addata></record> |
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| subjects | Activation Chemical industry Crystallography, X-Ray Cyclization Derivatives Ethylene Glycols - chemistry Glycols Joining Joint ventures macrocycles Macrocyclic compounds macrocyclic sulfates Magnetic Resonance Spectroscopy Molecular Conformation poly(ethylene glycol) Polyethylene Glycols - chemical synthesis Polyethylene Glycols - chemistry Precursors Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization Strategy Sulfates Synthesis synthetic methods |
| title | Highly Efficient Synthesis of Monodisperse Poly(ethylene glycols) and Derivatives through Macrocyclization of Oligo(ethylene glycols) |
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