Synthesis of 2-azido-2-deoxy- and 2-acetamido-2-deoxy-D-manno derivatives as versatile building blocks
Reported herein is the synthesis of a number of building blocks of 2-amino-2-deoxy-d-mannose from common d-glucose precursors. [Display omitted] •Chemical synthesis of a variety of derivatives of mannosamine has been completed using different approaches.•The synthesized compounds can be used as glyc...
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| Veröffentlicht in: | Carbohydrate research 2020-02, Vol.488, p.107900-107900, Article 107900 |
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| container_end_page | 107900 |
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| container_title | Carbohydrate research |
| container_volume | 488 |
| creator | Alex, Catherine Visansirikul, Satsawat Zhang, Yongzhen Yasomanee, Jagodige P. Codee, Jeroen Demchenko, Alexei V. |
| description | Reported herein is the synthesis of a number of building blocks of 2-amino-2-deoxy-d-mannose from common d-glucose precursors.
[Display omitted]
•Chemical synthesis of a variety of derivatives of mannosamine has been completed using different approaches.•The synthesized compounds can be used as glycosyl donors or glycosyl acceptors directly.•Other modifications of protecting and/or leaving groups can be easily incorporated.•The developed approaches are expected to expedite the synthesis of microbial glycans containing 2-acetamido-d-manno residues. |
| doi_str_mv | 10.1016/j.carres.2019.107900 |
| format | Article |
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[Display omitted]
•Chemical synthesis of a variety of derivatives of mannosamine has been completed using different approaches.•The synthesized compounds can be used as glycosyl donors or glycosyl acceptors directly.•Other modifications of protecting and/or leaving groups can be easily incorporated.•The developed approaches are expected to expedite the synthesis of microbial glycans containing 2-acetamido-d-manno residues.</description><identifier>ISSN: 0008-6215</identifier><identifier>EISSN: 1873-426X</identifier><identifier>DOI: 10.1016/j.carres.2019.107900</identifier><identifier>PMID: 31901454</identifier><language>eng</language><publisher>Netherlands: Elsevier Ltd</publisher><subject>amino sugars ; Carbohydrate Sequence ; carbohydrate structure ; chemical reactions ; glucose ; Glucose - chemistry ; Hexosamines - chemical synthesis ; Hexosamines - chemistry ; Mannose - analogs & derivatives ; Mannose - chemistry</subject><ispartof>Carbohydrate research, 2020-02, Vol.488, p.107900-107900, Article 107900</ispartof><rights>2019 Elsevier Ltd</rights><rights>Copyright © 2019 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c496t-b756ce067b96db71008c588e6964f109aaf81e9b573b5f18e8f50f13431a65b73</citedby><cites>FETCH-LOGICAL-c496t-b756ce067b96db71008c588e6964f109aaf81e9b573b5f18e8f50f13431a65b73</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0008621519306871$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>230,314,776,780,881,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31901454$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Alex, Catherine</creatorcontrib><creatorcontrib>Visansirikul, Satsawat</creatorcontrib><creatorcontrib>Zhang, Yongzhen</creatorcontrib><creatorcontrib>Yasomanee, Jagodige P.</creatorcontrib><creatorcontrib>Codee, Jeroen</creatorcontrib><creatorcontrib>Demchenko, Alexei V.</creatorcontrib><title>Synthesis of 2-azido-2-deoxy- and 2-acetamido-2-deoxy-D-manno derivatives as versatile building blocks</title><title>Carbohydrate research</title><addtitle>Carbohydr Res</addtitle><description>Reported herein is the synthesis of a number of building blocks of 2-amino-2-deoxy-d-mannose from common d-glucose precursors.
[Display omitted]
•Chemical synthesis of a variety of derivatives of mannosamine has been completed using different approaches.•The synthesized compounds can be used as glycosyl donors or glycosyl acceptors directly.•Other modifications of protecting and/or leaving groups can be easily incorporated.•The developed approaches are expected to expedite the synthesis of microbial glycans containing 2-acetamido-d-manno residues.</description><subject>amino sugars</subject><subject>Carbohydrate Sequence</subject><subject>carbohydrate structure</subject><subject>chemical reactions</subject><subject>glucose</subject><subject>Glucose - chemistry</subject><subject>Hexosamines - chemical synthesis</subject><subject>Hexosamines - chemistry</subject><subject>Mannose - analogs & derivatives</subject><subject>Mannose - chemistry</subject><issn>0008-6215</issn><issn>1873-426X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFUU1v1DAQtRCIbgv_AKEcuXixY8exL0iofBSpUg-0EjfLH5PWS2IXOxux_Hq82lLaC5xGM_PmzZt5CL2iZE0JFW83a2dyhrJuCVW11CtCnqAVlT3DvBXfnqIVIURi0dLuCB2XsqkpEb14jo4YVYTyjq_Q8HUX5xsooTRpaFpsfgWfcIs9pJ873Jjo90UHs5keNj7gycSYGg85LGYOC5TGlGaBXGo2QmO3YfQhXjd2TO57eYGeDWYs8PIunqCrTx8vT8_w-cXnL6fvz7HjSszY9p1wUEVaJbztadXvOilBKMEHSpQxg6SgbNcz2w1Ughw6MlDGGTWisz07Qe8OvLdbO4F3EOdsRn2bw2TyTicT9ONODDf6Oi26J7StyyvBmzuCnH5socx6CsXBOJoIaVt0ywmpj5Oy_z-UMaZapTitUH6AupxKyTDcK6JE793UG31wU-_d1Ac369jrh9fcD_2x7--5UH-6BMi6uADRgQ8Z3Kx9Cv_e8BskArKM</recordid><startdate>20200201</startdate><enddate>20200201</enddate><creator>Alex, Catherine</creator><creator>Visansirikul, Satsawat</creator><creator>Zhang, Yongzhen</creator><creator>Yasomanee, Jagodige P.</creator><creator>Codee, Jeroen</creator><creator>Demchenko, Alexei V.</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><scope>7S9</scope><scope>L.6</scope><scope>5PM</scope></search><sort><creationdate>20200201</creationdate><title>Synthesis of 2-azido-2-deoxy- and 2-acetamido-2-deoxy-D-manno derivatives as versatile building blocks</title><author>Alex, Catherine ; Visansirikul, Satsawat ; Zhang, Yongzhen ; Yasomanee, Jagodige P. ; Codee, Jeroen ; Demchenko, Alexei V.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c496t-b756ce067b96db71008c588e6964f109aaf81e9b573b5f18e8f50f13431a65b73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>amino sugars</topic><topic>Carbohydrate Sequence</topic><topic>carbohydrate structure</topic><topic>chemical reactions</topic><topic>glucose</topic><topic>Glucose - chemistry</topic><topic>Hexosamines - chemical synthesis</topic><topic>Hexosamines - chemistry</topic><topic>Mannose - analogs & derivatives</topic><topic>Mannose - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Alex, Catherine</creatorcontrib><creatorcontrib>Visansirikul, Satsawat</creatorcontrib><creatorcontrib>Zhang, Yongzhen</creatorcontrib><creatorcontrib>Yasomanee, Jagodige P.</creatorcontrib><creatorcontrib>Codee, Jeroen</creatorcontrib><creatorcontrib>Demchenko, Alexei V.</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><collection>AGRICOLA</collection><collection>AGRICOLA - 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>Alex, Catherine</au><au>Visansirikul, Satsawat</au><au>Zhang, Yongzhen</au><au>Yasomanee, Jagodige P.</au><au>Codee, Jeroen</au><au>Demchenko, Alexei V.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of 2-azido-2-deoxy- and 2-acetamido-2-deoxy-D-manno derivatives as versatile building blocks</atitle><jtitle>Carbohydrate research</jtitle><addtitle>Carbohydr Res</addtitle><date>2020-02-01</date><risdate>2020</risdate><volume>488</volume><spage>107900</spage><epage>107900</epage><pages>107900-107900</pages><artnum>107900</artnum><issn>0008-6215</issn><eissn>1873-426X</eissn><abstract>Reported herein is the synthesis of a number of building blocks of 2-amino-2-deoxy-d-mannose from common d-glucose precursors.
[Display omitted]
•Chemical synthesis of a variety of derivatives of mannosamine has been completed using different approaches.•The synthesized compounds can be used as glycosyl donors or glycosyl acceptors directly.•Other modifications of protecting and/or leaving groups can be easily incorporated.•The developed approaches are expected to expedite the synthesis of microbial glycans containing 2-acetamido-d-manno residues.</abstract><cop>Netherlands</cop><pub>Elsevier Ltd</pub><pmid>31901454</pmid><doi>10.1016/j.carres.2019.107900</doi><tpages>1</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0008-6215 |
| ispartof | Carbohydrate research, 2020-02, Vol.488, p.107900-107900, Article 107900 |
| issn | 0008-6215 1873-426X |
| language | eng |
| recordid | cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_7012756 |
| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | amino sugars Carbohydrate Sequence carbohydrate structure chemical reactions glucose Glucose - chemistry Hexosamines - chemical synthesis Hexosamines - chemistry Mannose - analogs & derivatives Mannose - chemistry |
| title | Synthesis of 2-azido-2-deoxy- and 2-acetamido-2-deoxy-D-manno derivatives as versatile building blocks |
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