Next Article in Journal
Protective Effect of 2,4′,5′-Trihydroxyl-5,2′-dibromo diphenylmethanone, a New Halophenol, against Hydrogen Peroxide-Induced EA.hy926 Cells Injury
Next Article in Special Issue
Polysaccharides from the Marine Environment with Pharmacological, Cosmeceutical and Nutraceutical Potential
Previous Article in Journal
Isolation, Characterization, Crystal Structure Elucidation of Two Flavanones and Simultaneous RP-HPLC Determination of Five Major Compounds from Syzygium campanulatum Korth
Previous Article in Special Issue
A Survey of Recent Synthetic Applications of 2,3-Dideoxy-Hex-2-enopyranosides
Article Menu

Export Article

Open AccessArticle
Molecules 2015, 20(8), 14234-14253; doi:10.3390/molecules200814234

An Unusual Carbohydrate Conformation is Evident in Moraxella catarrhalis Oligosaccharides

1
Biognos AB, Generatorsgatan 1, 41705 Gothenburg, Sweden
2
Institute for Glycomics, Gold Coast Campus, Griffith University, 4222 Queensland, Australia
3
Institute for Glycomics and School of Medical Science, Gold Coast Campus, Griffith University, 4222 Queensland, Australia
4
Menzies Health Institute and School of Medical Science, Gold Coast Campus, Griffith University, 4222 Queensland, Australia
*
Author to whom correspondence should be addressed.
Academic Editor: Vito Ferro
Received: 23 May 2015 / Revised: 24 July 2015 / Accepted: 27 July 2015 / Published: 5 August 2015
(This article belongs to the Collection Advances in Carbohydrate Chemistry)
View Full-Text   |   Download PDF [3093 KB, uploaded 5 August 2015]   |  

Abstract

Oligosaccharide structures derived from the lipooligosaccharide of M. catarrhalis show that the highly branched glucose-rich inner core of the oligosaccharide has an altered conformation compared to the most truncated tetra-glucose-Kdo lgt1/4Δ oligosaccharide structure. Addition of one residue each to the (1-4) and (1-6) chains to give the lgt2Δ oligosaccharide is the minimum requirement for this conformational change to occur. Extensive molecular modeling and NMR investigations have shown that the (1-3), (1-4), and (1-6) glycosidic linkages from the central α-D-Glcp have significantly altered conformational preferences between the two structures. For the lgt1/4Δ oligosaccharide the (1-3) and (1-4) linkage populates predominantly the syn minimum on the conformational free energy map and for the (1-6) linkage conformational flexibility is observed, which is supported by 1H-NMR T1 measurements. For the lgt2Δ oligosaccharide the unusual “(1-4)anti-ψ(1-6)gg” conformation, which could be confirmed by long-range NOE signals, is a dominant conformation in which the oligosaccharide is very compact with the terminal α-D-GlcNAc residue folding back towards the center of the molecule leading to an extensive intra-molecular hydrophobic interaction between the terminal residues. Comparing effective H-H distances, which were calculated for conformational sub-ensembles, with the NOE distances revealed that typically multiple conformations could be present without significantly violating the measured NOE restraints. For lgt2Δ the presence of more than one conformation is supported by the NOE data. View Full-Text
Keywords: carbohydrate conformations; oligosaccharides; molecular dynamics simulations; NMR carbohydrate conformations; oligosaccharides; molecular dynamics simulations; NMR
Figures

Figure 1

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

Supplementary material

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

Frank, M.; Collins, P.M.; Peak, I.R.; Grice, I.D.; Wilson, J.C. An Unusual Carbohydrate Conformation is Evident in Moraxella catarrhalis Oligosaccharides. Molecules 2015, 20, 14234-14253.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top