Total Synthesis of Native 5,7-Diacetylpseudaminic Acid from N‑Acetylneuraminic Acid

The pseudaminic acids are a family of 5,7-diamino-3,5,7,9-tetradeoxynonulosonic acids that are functional components of flagellin and pili proteins within clinically relevant Gram-negative bacteria. Herein, we describe the total synthesis of the most common pseudaminic acid, 5,7-diacetylpseudaminic...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2016-03, Vol.81 (6), p.2607-2611
Main Authors: Williams, James T, Corcilius, Leo, Kiefel, Milton J, Payne, Richard J
Format: Article
Language:English
Subjects:
Fimbriae Proteins - chemistry
Flagellin - chemistry
Glycosylation
Gram-Negative Bacteria - chemistry
Magnetic Resonance Spectroscopy
N-Acetylneuraminic Acid - chemistry
Sugar Acids - chemical synthesis
Sugar Acids - chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-a374t-6783fb4ee33ba821e2e40de14ec59a81bb5b771274c898c637802bb5d7f372253
cites cdi_FETCH-LOGICAL-a374t-6783fb4ee33ba821e2e40de14ec59a81bb5b771274c898c637802bb5d7f372253
container_end_page 2611
container_issue 6
container_start_page 2607
container_title Journal of organic chemistry
container_volume 81
creator Williams, James T
Corcilius, Leo
Kiefel, Milton J
Payne, Richard J
description The pseudaminic acids are a family of 5,7-diamino-3,5,7,9-tetradeoxynonulosonic acids that are functional components of flagellin and pili proteins within clinically relevant Gram-negative bacteria. Herein, we describe the total synthesis of the most common pseudaminic acid, 5,7-diacetylpseudaminic acid, from N-acetylneuraminic acid. The divergent nature of the route reported here provides a robust and versatile means to access other members of the family, together with analogues, for probing the functional role of the pseudaminic acids and pseudaminic acid derived proteins in the future.
doi_str_mv 10.1021/acs.joc.5b02754
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1774529961</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1774529961</sourcerecordid><originalsourceid>FETCH-LOGICAL-a374t-6783fb4ee33ba821e2e40de14ec59a81bb5b771274c898c637802bb5d7f372253</originalsourceid><addsrcrecordid>eNp1kE1Lw0AQhhdRbK2evUmOgqbdz2xyLPUTpB5sz8tmM8Et-ai7idCbf8G_6C9xtVW8OJeBmWdemAehU4LHBFMy0caPV60ZixxTKfgeGhJBcZxkmO-jIcaUxowmbICOvF_hUEKIQzSgAZAiSYZouWg7XUVPm6Z7Bm991JbRXHf2FSJxKeMrqw10m2rtoS90bRtroqmxRVS6to7mH2_v0-99A737sz5GB6WuPJzs-ggtb64Xs7v44fH2fjZ9iDWTvIsTmbIy5wCM5TqlBChwXADhYESmU5LnIpeSUMlNmqUmYTLFNAwLWTJJqWAjdL7NXbv2pQffqdp6A1WlG2h7r4iUXNAsS0hAJ1vUuNZ7B6VaO1trt1EEqy-XKrhUwaXauQwXZ7vwPq-h-OV_5AXgYgtsL3vXhF__jfsEsFp_Tg</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1774529961</pqid></control><display><type>article</type><title>Total Synthesis of Native 5,7-Diacetylpseudaminic Acid from N‑Acetylneuraminic Acid</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read &amp; Publish Agreement 2022-2024 (Reading list)</source><creator>Williams, James T ; Corcilius, Leo ; Kiefel, Milton J ; Payne, Richard J</creator><creatorcontrib>Williams, James T ; Corcilius, Leo ; Kiefel, Milton J ; Payne, Richard J</creatorcontrib><description>The pseudaminic acids are a family of 5,7-diamino-3,5,7,9-tetradeoxynonulosonic acids that are functional components of flagellin and pili proteins within clinically relevant Gram-negative bacteria. Herein, we describe the total synthesis of the most common pseudaminic acid, 5,7-diacetylpseudaminic acid, from N-acetylneuraminic acid. The divergent nature of the route reported here provides a robust and versatile means to access other members of the family, together with analogues, for probing the functional role of the pseudaminic acids and pseudaminic acid derived proteins in the future.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/acs.joc.5b02754</identifier><identifier>PMID: 26907566</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Fimbriae Proteins - chemistry ; Flagellin - chemistry ; Glycosylation ; Gram-Negative Bacteria - chemistry ; Magnetic Resonance Spectroscopy ; N-Acetylneuraminic Acid - chemistry ; Sugar Acids - chemical synthesis ; Sugar Acids - chemistry</subject><ispartof>Journal of organic chemistry, 2016-03, Vol.81 (6), p.2607-2611</ispartof><rights>Copyright © 2016 American Chemical Society</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a374t-6783fb4ee33ba821e2e40de14ec59a81bb5b771274c898c637802bb5d7f372253</citedby><cites>FETCH-LOGICAL-a374t-6783fb4ee33ba821e2e40de14ec59a81bb5b771274c898c637802bb5d7f372253</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27922,27923</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26907566$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Williams, James T</creatorcontrib><creatorcontrib>Corcilius, Leo</creatorcontrib><creatorcontrib>Kiefel, Milton J</creatorcontrib><creatorcontrib>Payne, Richard J</creatorcontrib><title>Total Synthesis of Native 5,7-Diacetylpseudaminic Acid from N‑Acetylneuraminic Acid</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>The pseudaminic acids are a family of 5,7-diamino-3,5,7,9-tetradeoxynonulosonic acids that are functional components of flagellin and pili proteins within clinically relevant Gram-negative bacteria. Herein, we describe the total synthesis of the most common pseudaminic acid, 5,7-diacetylpseudaminic acid, from N-acetylneuraminic acid. The divergent nature of the route reported here provides a robust and versatile means to access other members of the family, together with analogues, for probing the functional role of the pseudaminic acids and pseudaminic acid derived proteins in the future.</description><subject>Fimbriae Proteins - chemistry</subject><subject>Flagellin - chemistry</subject><subject>Glycosylation</subject><subject>Gram-Negative Bacteria - chemistry</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>N-Acetylneuraminic Acid - chemistry</subject><subject>Sugar Acids - chemical synthesis</subject><subject>Sugar Acids - chemistry</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNp1kE1Lw0AQhhdRbK2evUmOgqbdz2xyLPUTpB5sz8tmM8Et-ai7idCbf8G_6C9xtVW8OJeBmWdemAehU4LHBFMy0caPV60ZixxTKfgeGhJBcZxkmO-jIcaUxowmbICOvF_hUEKIQzSgAZAiSYZouWg7XUVPm6Z7Bm991JbRXHf2FSJxKeMrqw10m2rtoS90bRtroqmxRVS6to7mH2_v0-99A737sz5GB6WuPJzs-ggtb64Xs7v44fH2fjZ9iDWTvIsTmbIy5wCM5TqlBChwXADhYESmU5LnIpeSUMlNmqUmYTLFNAwLWTJJqWAjdL7NXbv2pQffqdp6A1WlG2h7r4iUXNAsS0hAJ1vUuNZ7B6VaO1trt1EEqy-XKrhUwaXauQwXZ7vwPq-h-OV_5AXgYgtsL3vXhF__jfsEsFp_Tg</recordid><startdate>20160318</startdate><enddate>20160318</enddate><creator>Williams, James T</creator><creator>Corcilius, Leo</creator><creator>Kiefel, Milton J</creator><creator>Payne, Richard J</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>7X8</scope></search><sort><creationdate>20160318</creationdate><title>Total Synthesis of Native 5,7-Diacetylpseudaminic Acid from N‑Acetylneuraminic Acid</title><author>Williams, James T ; Corcilius, Leo ; Kiefel, Milton J ; Payne, Richard J</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a374t-6783fb4ee33ba821e2e40de14ec59a81bb5b771274c898c637802bb5d7f372253</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Fimbriae Proteins - chemistry</topic><topic>Flagellin - chemistry</topic><topic>Glycosylation</topic><topic>Gram-Negative Bacteria - chemistry</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>N-Acetylneuraminic Acid - chemistry</topic><topic>Sugar Acids - chemical synthesis</topic><topic>Sugar Acids - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Williams, James T</creatorcontrib><creatorcontrib>Corcilius, Leo</creatorcontrib><creatorcontrib>Kiefel, Milton J</creatorcontrib><creatorcontrib>Payne, Richard J</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>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Williams, James T</au><au>Corcilius, Leo</au><au>Kiefel, Milton J</au><au>Payne, Richard J</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Total Synthesis of Native 5,7-Diacetylpseudaminic Acid from N‑Acetylneuraminic Acid</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2016-03-18</date><risdate>2016</risdate><volume>81</volume><issue>6</issue><spage>2607</spage><epage>2611</epage><pages>2607-2611</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>The pseudaminic acids are a family of 5,7-diamino-3,5,7,9-tetradeoxynonulosonic acids that are functional components of flagellin and pili proteins within clinically relevant Gram-negative bacteria. Herein, we describe the total synthesis of the most common pseudaminic acid, 5,7-diacetylpseudaminic acid, from N-acetylneuraminic acid. The divergent nature of the route reported here provides a robust and versatile means to access other members of the family, together with analogues, for probing the functional role of the pseudaminic acids and pseudaminic acid derived proteins in the future.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>26907566</pmid><doi>10.1021/acs.joc.5b02754</doi><tpages>5</tpages><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 0022-3263
ispartof Journal of organic chemistry, 2016-03, Vol.81 (6), p.2607-2611
issn 0022-3263
1520-6904
language eng
recordid cdi_proquest_miscellaneous_1774529961
source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
subjects Fimbriae Proteins - chemistry
Flagellin - chemistry
Glycosylation
Gram-Negative Bacteria - chemistry
Magnetic Resonance Spectroscopy
N-Acetylneuraminic Acid - chemistry
Sugar Acids - chemical synthesis
Sugar Acids - chemistry
title Total Synthesis of Native 5,7-Diacetylpseudaminic Acid from N‑Acetylneuraminic Acid
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-14T14%3A08%3A45IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Total%20Synthesis%20of%20Native%205,7-Diacetylpseudaminic%20Acid%20from%20N%E2%80%91Acetylneuraminic%20Acid&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Williams,%20James%20T&rft.date=2016-03-18&rft.volume=81&rft.issue=6&rft.spage=2607&rft.epage=2611&rft.pages=2607-2611&rft.issn=0022-3263&rft.eissn=1520-6904&rft_id=info:doi/10.1021/acs.joc.5b02754&rft_dat=%3Cproquest_cross%3E1774529961%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a374t-6783fb4ee33ba821e2e40de14ec59a81bb5b771274c898c637802bb5d7f372253%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=1774529961&rft_id=info:pmid/26907566&rfr_iscdi=true