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Article: Total Synthesis of Pseudomonas aeruginosa 1244 Pilin Glycan via de Novo Synthesis of Pseudaminic Acid

TitleTotal Synthesis of Pseudomonas aeruginosa 1244 Pilin Glycan via de Novo Synthesis of Pseudaminic Acid
Authors
Issue Date2017
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/jacsat/index.html
Citation
Journal of the American Chemical Society, 2017, v. 139 n. 38, p. 13420-13428 How to Cite?
AbstractPseudaminic acid (Pse) is a nonulosonic acid unique to bacterial species, found as a component of important cell surface glycans and glycoproteins in various pathogenic species, such as the critical hospital threat Pseudomonas aeruginosa. Herein we present the development of a facile and scalable de novo synthesis of Pse and its functionalized derivatives from easily available Cbz-l-allo-threonine methyl ester (16 steps in 11% yield). The key reactions in our de novo synthesis involve the diastereoselective glycine thioester isonitrile-based aldol-type reaction to create the 1,3-anti-diamino skeleton, followed by the Fukuyama reduction and the indium-mediated Barbier-type allylation. Moreover, we have studied the glycosylation of the Pse glycosyl donors and identified the structural determinants for its glycosylation diastereoselectivity, which enabled us to complete the total synthesis of P. aeruginosa 1244 pilin trisaccharide α-5NβOHC47NFmPse-(2→4)-β-Xyl-(1→3)-FucNAc.
Persistent Identifierhttp://hdl.handle.net/10722/256265
ISSN
2019 Impact Factor: 14.612
2015 SCImago Journal Rankings: 7.123
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorLiu, H-
dc.contributor.authorZhang, Y-
dc.contributor.authorWei, R-
dc.contributor.authorAndolina, G-
dc.contributor.authorLi, X-
dc.date.accessioned2018-07-20T06:31:55Z-
dc.date.available2018-07-20T06:31:55Z-
dc.date.issued2017-
dc.identifier.citationJournal of the American Chemical Society, 2017, v. 139 n. 38, p. 13420-13428-
dc.identifier.issn0002-7863-
dc.identifier.urihttp://hdl.handle.net/10722/256265-
dc.description.abstractPseudaminic acid (Pse) is a nonulosonic acid unique to bacterial species, found as a component of important cell surface glycans and glycoproteins in various pathogenic species, such as the critical hospital threat Pseudomonas aeruginosa. Herein we present the development of a facile and scalable de novo synthesis of Pse and its functionalized derivatives from easily available Cbz-l-allo-threonine methyl ester (16 steps in 11% yield). The key reactions in our de novo synthesis involve the diastereoselective glycine thioester isonitrile-based aldol-type reaction to create the 1,3-anti-diamino skeleton, followed by the Fukuyama reduction and the indium-mediated Barbier-type allylation. Moreover, we have studied the glycosylation of the Pse glycosyl donors and identified the structural determinants for its glycosylation diastereoselectivity, which enabled us to complete the total synthesis of P. aeruginosa 1244 pilin trisaccharide α-5NβOHC47NFmPse-(2→4)-β-Xyl-(1→3)-FucNAc.-
dc.languageeng-
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/jacsat/index.html-
dc.relation.ispartofJournal of the American Chemical Society-
dc.titleTotal Synthesis of Pseudomonas aeruginosa 1244 Pilin Glycan via de Novo Synthesis of Pseudaminic Acid-
dc.typeArticle-
dc.identifier.emailLiu, H: liuhan@HKUCC-COM.hku.hk-
dc.identifier.emailAndolina, G: andolina@HKUCC-COM.hku.hk-
dc.identifier.emailLi, X: xuechenl@hku.hk-
dc.identifier.authorityLiu, H=rp02748-
dc.identifier.authorityLi, X=rp00742-
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1021/jacs.7b06055-
dc.identifier.pmid28837324-
dc.identifier.scopuseid_2-s2.0-85030118182-
dc.identifier.hkuros286389-
dc.identifier.volume139-
dc.identifier.issue38-
dc.identifier.spage13420-
dc.identifier.epage13428-
dc.identifier.isiWOS:000412043000026-
dc.publisher.placeUnited States-

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