dc.contributor.author
Seeberger, Peter H.
dc.contributor.author
Pereira, Claney L.
dc.contributor.author
Govindan, Subramanian
dc.date.accessioned
2018-06-08T11:00:16Z
dc.date.available
2017-04-28T10:29:29.277Z
dc.identifier.uri
https://refubium.fu-berlin.de/handle/fub188/21453
dc.identifier.uri
http://dx.doi.org/10.17169/refubium-24746
dc.description.abstract
The Gram-positive bacterium Streptococcus pneumoniae causes severe disease
globally. Vaccines that prevent S. pneumoniae infections induce antibodies
against epitopes within the bacterial capsular polysaccharide (CPS). A better
immunological understanding of the epitopes that protect from bacterial
infection requires defined oligosaccharides obtained by total synthesis. The
key to the synthesis of the S. pneumoniae serotype 12F CPS hexasaccharide
repeating unit that is not contained in currently used glycoconjugate vaccines
is the assembly of the trisaccharide
β-D-GalpNAc-(1→4)-[α-D-Glcp-(1→3)]-β-D-ManpNAcA, in which the branching points
are equipped with orthogonal protecting groups. A linear approach relying on
the sequential assembly of monosaccharide building blocks proved superior to a
convergent [3 + 3] strategy that was not successful due to steric constraints.
The synthetic hexasaccharide is the starting point for further immunological
investigations.
en
dc.rights.uri
http://creativecommons.org/licenses/by/4.0/
dc.subject
carbohydrate antigen
dc.subject
oligosaccharides
dc.subject
Streptococcus pneumoniae
dc.subject
total synthesis
dc.subject.ddc
500 Naturwissenschaften und Mathematik::540 Chemie
dc.title
Total synthesis of a Streptococcus pneumoniae serotype 12F CPS repeating unit
hexasaccharide
dc.type
Wissenschaftlicher Artikel
dcterms.bibliographicCitation
Beilstein J. Org. Chem. - 13 (2017), S. 164-173
dcterms.bibliographicCitation.doi
10.3762/bjoc.13.19
dcterms.bibliographicCitation.url
http://www.beilstein-journals.org/bjoc/articles/13/19
refubium.affiliation
Biologie, Chemie, Pharmazie
de
refubium.mycore.fudocsId
FUDOCS_document_000000026927
refubium.note.author
Der Artikel wurde in einer reinen Open-Access-Zeitschrift publiziert.
refubium.resourceType.isindependentpub
no
refubium.mycore.derivateId
FUDOCS_derivate_000000008112
dcterms.accessRights.openaire
open access