Ändra sökning
RefereraExporteraLänk till posten
Permanent länk

Direktlänk
Referera
Referensformat
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Annat format
Fler format
Språk
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Annat språk
Fler språk
Utmatningsformat
  • html
  • text
  • asciidoc
  • rtf
Direct Evidence for Hydrogen Bonding in Glycans: A Combined NMR and Molecular Dynamics Study
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
2013 (Engelska)Ingår i: Journal of Physical Chemistry B, ISSN 1520-6106, E-ISSN 1520-5207, Vol. 117, nr 17, s. 4860-4869Artikel i tidskrift (Refereegranskat) Published
Abstract [en]

We introduce the abundant hydroxyl groups of glycans as NMR handle's and structural probes to expand the repertoire of tools for structure function studies on glycans in solution. To this end, we present the facile detection and assignment of hydroxyl groups in a Wide range of sample concentrations (0.5-1700 mM) and temperatures, ranging from -5 to 25 degrees C.,We then exploit this information to directly detect hydrogen bonds, well-known for their importance in molecular structural determination through NMR. Via HSQC-TOCSY, we were able to determine the directionality; of these hydrogen bonds in sucrose Furthermore, by means Of molecular dynamics simulations in conjunction with NMR, we establish that one Out of the three detected hydrogen bonds arises from intermolecular interactions. This finding may shed light on glycan glycan interactions and glycan recognition by proteins.

Ort, förlag, år, upplaga, sidor
2013. Vol. 117, nr 17, s. 4860-4869
Nationell ämneskategori
Fysikalisk kemi Organisk kemi
Forskningsämne
organisk kemi
Identifikatorer
URN: urn:nbn:se:su:diva-91041DOI: 10.1021/jp400402bISI: 000318536700015OAI: oai:DiVA.org:su-91041DiVA, id: diva2:630485
Forskningsfinansiär
Vetenskapsrådet
Anmärkning

AuthorCount:4;

Tillgänglig från: 2013-06-19 Skapad: 2013-06-18 Senast uppdaterad: 2017-12-06Bibliografiskt granskad
Ingår i avhandling
1. Conformations of Flexible Oligosaccharides: Molecular Simulations and NMR spectroscopy
Öppna denna publikation i ny flik eller fönster >>Conformations of Flexible Oligosaccharides: Molecular Simulations and NMR spectroscopy
2013 (Engelska)Doktorsavhandling, sammanläggning (Övrigt vetenskapligt)
Abstract [en]

The conformational preferences of several oligosaccharides are investigated herein using a combination of NMR spectroscopy and molecular dynamics (MD) simulations, focusing on the torsion angles associated with the glycosidic linkages.

Strategies for obtaining usable J-HMBC spectra for carbons with an adjacent 13C label are described. By employing a selective pulse or a constant time modification, spectra free from interferences are obtained for site-specifically 13C labeled oligosaccharides.

Intermolecular hydrogen bonding in sucrose is investigated using MD simulations performed at different concentrations. One of the most frequent intermolecular hydrogen bonds in the simulations, O3f∙∙∙HO3g, was detected using the HSQC-TOCSY NMR experiment.

Based on MD simulations and NMR spectroscopy, the conformational ensemble for a trisaccharide segment of the LeaLex hexasaccharide is proposed to feature conformational exchange between conformations with positive and negative values for the ψ3 torsion angle in the β-D-GlcpNAc-(1→3)-β-D-Galp linkage.

Using MD simulations, the conformation of the N-acetyl group is shown to influence the glycosidic conformation at a nearby linkage in two oligosaccharides.

Short (1→6)-linked oligosaccharides are shown to exhibit conformational exchange at the ω and ψ torsion angles. Notably, the former torsion angle populates states with ψ ≈ ±90°. Conformationally sensitive homo- and heteronuclear coupling constants are determined using various NMR experiments. The experimental data, including effective distances from NOESY obtained for two of the compounds, is used to improve the representation of the ω torsion angle in the CHARMM36 force field.

Ort, förlag, år, upplaga, sidor
Stockholm: Department of Organic Chemistry, Stockholm University, 2013. s. 78
Nyckelord
Carbohydrates, Oligosaccharide, Conformation, NMR spectroscopy, MD simulations
Nationell ämneskategori
Organisk kemi
Forskningsämne
organisk kemi
Identifikatorer
urn:nbn:se:su:diva-95480 (URN)978-91-7447-808-2 (ISBN)
Disputation
2013-12-13, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 16 B, Stockholm, 10:00 (Engelska)
Opponent
Handledare
Anmärkning

At the time of the doctoral defense, the following papers were unpublished and had a status as follows: Paper 1: Manuscript. Paper 5: Accepted. Paper 6: Manuscript.

Tillgänglig från: 2013-11-21 Skapad: 2013-10-29 Senast uppdaterad: 2015-10-06Bibliografiskt granskad

Open Access i DiVA

fulltext(3207 kB)203 nedladdningar
Filinformation
Filnamn FULLTEXT01.pdfFilstorlek 3207 kBChecksumma SHA-512
2f950c7466bf7c6a10d92071ca9f8aa7dbb94c3d808416d2c4e284f8327434b63d1c9a070574b9042f74848ffd4a0f750051f55311957925a23d0458154569bd
Typ fulltextMimetyp application/pdf

Övriga länkar

Förlagets fulltext

Sök vidare i DiVA

Av författaren/redaktören
Pendrill, RobertWidmalm, Göran
Av organisationen
Institutionen för organisk kemi
I samma tidskrift
Journal of Physical Chemistry B
Fysikalisk kemiOrganisk kemi

Sök vidare utanför DiVA

GoogleGoogle Scholar
Totalt: 203 nedladdningar
Antalet nedladdningar är summan av nedladdningar för alla fulltexter. Det kan inkludera t.ex tidigare versioner som nu inte längre är tillgängliga.

doi
urn-nbn

Altmetricpoäng

doi
urn-nbn
Totalt: 121 träffar
RefereraExporteraLänk till posten
Permanent länk

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