Endre søk
RefereraExporteraLink to record
Permanent link

Direct link
Referera
Referensformat
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Annet format
Fler format
Språk
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Annet språk
Fler språk
Utmatningsformat
  • html
  • text
  • asciidoc
  • rtf
Structural Studies of the O-Acetyl-Containing O-Antigen from a Shigella flexneri Serotype 6 Strain and Synthesis of Oligosaccharide Fragments Thereof
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Vise andre og tillknytning
2013 (engelsk)Inngår i: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, nr 19, s. 4085-4106Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

Extensive analysis by NMR spectroscopy of the delipidated lipopolysaccharide of Shigella flexneri serotype 6 strain MDC 2924-71 confirmed the most recently reported structure of the O-antigen repeating unit as {4)--D-GalpA-(13)--D-GalpNAc-(12)--L-Rhap3Ac/4Ac-(12)--L-Rhap-(1}, and revealed the non-stoichiometric acetylation at O-3C/4C. Input from the CASPER program helped to ascertain the fine distribution of the three possible patterns of O-acetylation. The non-O-acetylated repeating unit (ABCD) corresponded to about 2/3 of the population, while 1/4 was acetylated at O-3C (3AcCDAB), and 1/10 at O-4C (4AcCDAB). Di- to tetrasaccharides with a GalpA residue (A) at their reducing end were synthesized as their propyl glycosides following a multistep linear strategy relying on late-stage acetylation at O-3C. Thus, the 3C-O-acetylated and non-O-acetylated targets were synthesized from common protected intermediates. Rhamnosylation was most efficiently achieved by using imidate donors, including at O-4 of a benzyl galacturonate acceptor. In contrast, a thiophenyl 2-deoxy-2-trichloroacetamido-D-galactopyranoside precursor was preferred for chain elongation involving residue B. Final Pd/C-mediated deprotection ensured O-acetyl stability. All of the target molecules represent parts of the O-antigen of S. flexneri 6, a prevalent serotype. Non-O-acetylated oligosaccharides are also fragments of the Escherichia coli O147 O-antigen.

sted, utgiver, år, opplag, sider
2013. nr 19, s. 4085-4106
Emneord [en]
Carbohydrates, Glycosylation, Oligosaccharides, NMR spectroscopy, Structure elucidation, Polysaccharides
HSV kategori
Identifikatorer
URN: urn:nbn:se:su:diva-92505DOI: 10.1002/ejoc.201300180ISI: 000320720100021OAI: oai:DiVA.org:su-92505DiVA, id: diva2:639786
Forskningsfinansiär
Swedish Research CouncilKnut and Alice Wallenberg FoundationEU, FP7, Seventh Framework Programme
Merknad

AuthorCount:7;

Tilgjengelig fra: 2013-08-09 Laget: 2013-08-07 Sist oppdatert: 2018-03-01bibliografisk kontrollert

Open Access i DiVA

fulltext(846 kB)59 nedlastinger
Filinformasjon
Fil FULLTEXT01.pdfFilstørrelse 846 kBChecksum SHA-512
0d256daeec49871d5702974d6580e34fc965d137b92079b03f0ae12020d9fb05f2b228bfd42ff6271ed43ef7eab67e0b5cb8c282b6e31ae54f8a7292b3057acd
Type fulltextMimetype application/pdf

Andre lenker

Forlagets fulltekst

Søk i DiVA

Av forfatter/redaktør
Fontana, CarolinaWidmalm, Göran
Av organisasjonen
I samme tidsskrift
European Journal of Organic Chemistry

Søk utenfor DiVA

GoogleGoogle Scholar
Totalt: 59 nedlastinger
Antall nedlastinger er summen av alle nedlastinger av alle fulltekster. Det kan for eksempel være tidligere versjoner som er ikke lenger tilgjengelige

doi
urn-nbn

Altmetric

doi
urn-nbn
Totalt: 133 treff
RefereraExporteraLink to record
Permanent link

Direct link
Referera
Referensformat
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Annet format
Fler format
Språk
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Annet språk
Fler språk
Utmatningsformat
  • html
  • text
  • asciidoc
  • rtf