dc.contributor.author
Zhang, Shuo
dc.contributor.author
Seeberger, Peter H.
dc.date.accessioned
2022-01-03T12:02:51Z
dc.date.available
2022-01-03T12:02:51Z
dc.identifier.uri
https://refubium.fu-berlin.de/handle/fub188/32952
dc.identifier.uri
http://dx.doi.org/10.17169/refubium-32678
dc.description.abstract
Acinetobacter baumannii is an opportunistic pathogen that causes serious nosocomial infections. One of the multidrug-resistant strains, AB5075, can result in bacteremia, pneumonia and wound infections associated with high morbidity and mortality. The structurally unique glycans on the surface of these bacteria are attractive targets for the development of glycoconjugate vaccines. Here, we report the first total synthesis of the densely functionalized trisaccharide repeating unit of A. baumannii AB5075 as well as two analogues. The construction of 1,2-cis linkages between the rare sugars relies on a double-serial inversion strategy. The judicious selection of building blocks and reaction conditions allowed for stereoselective glycosylations, the installation of acetamido groups and the (S)-3-hydroxybutanoyl chain.
en
dc.format.extent
8 Seiten
dc.rights.uri
https://creativecommons.org/licenses/by-nc-nd/4.0/
dc.subject
carbohydrates
en
dc.subject
oligosaccharides
en
dc.subject
total synthesis
en
dc.subject.ddc
500 Naturwissenschaften und Mathematik::540 Chemie::540 Chemie und zugeordnete Wissenschaften
dc.title
Total Syntheses of Conjugation-Ready Repeating Units of Acinetobacter baumannii AB5075 for Glycoconjugate Vaccine Development
dc.type
Wissenschaftlicher Artikel
dcterms.bibliographicCitation.doi
10.1002/chem.202103234
dcterms.bibliographicCitation.journaltitle
Chemistry - A European Journal
dcterms.bibliographicCitation.number
69
dcterms.bibliographicCitation.pagestart
17444
dcterms.bibliographicCitation.pageend
17451
dcterms.bibliographicCitation.volume
27
dcterms.bibliographicCitation.url
https://doi.org/10.1002/chem.202103234
refubium.affiliation
Biologie, Chemie, Pharmazie
refubium.affiliation.other
Institut für Chemie und Biochemie
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refubium.resourceType.isindependentpub
no
dcterms.accessRights.openaire
open access
dcterms.isPartOf.eissn
1521-3765
refubium.resourceType.provider
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