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Comparative 1H NMR study of hydroxy protons in galabioside and its S-linked 4-thiodisaccharide analogue in aqueous solution

Sandström, Corine ; Magnusson, Göran LU ; Nilsson, Ulf LU and Kenne, Lennart (1999) In Carbohydrate Research 322(1-2). p.46-56
Abstract

The NMR data obtained from hydroxy protons have been used to investigate the presence and absence of intramolecular hydrogen bonding in aqueous solutions of 2-(trimethylsilyl)ethyl galabioside (α-D-Galp-(1→4)-β-D-Galp-O(CH2)2SiMe3) and the S-linked 4-thiodisaccharide analogue. The data show that there is a weak hydrogen bond interaction between O-6H and O-2'H in galabioside, but not in the thio-analogue. The results are in good agreement with those reported for the substances in a Me2SO-d6 solution. It is also shown that the existence of a hydrogen bond can be quite easily monitored by comparing the NMR data of the hydroxy protons.

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author
; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
Conformation analysis, Galabioside, Hydrogen bonds, Hydroxy protons, NMR, Thioglycoside
in
Carbohydrate Research
volume
322
issue
1-2
pages
11 pages
publisher
Elsevier
external identifiers
  • scopus:0032585781
  • pmid:10629948
ISSN
0008-6215
DOI
10.1016/S0008-6215(99)00215-3
language
English
LU publication?
yes
id
657b3dd6-9eec-4f58-94f2-3119873a6181
date added to LUP
2023-02-07 08:58:34
date last changed
2024-01-03 22:03:37
@article{657b3dd6-9eec-4f58-94f2-3119873a6181,
  abstract     = {{<p>The NMR data obtained from hydroxy protons have been used to investigate the presence and absence of intramolecular hydrogen bonding in aqueous solutions of 2-(trimethylsilyl)ethyl galabioside (α-D-Galp-(1→4)-β-D-Galp-O(CH<sub>2</sub>)<sub>2</sub>SiMe<sub>3</sub>) and the S-linked 4-thiodisaccharide analogue. The data show that there is a weak hydrogen bond interaction between O-6H and O-2'H in galabioside, but not in the thio-analogue. The results are in good agreement with those reported for the substances in a Me<sub>2</sub>SO-d<sub>6</sub> solution. It is also shown that the existence of a hydrogen bond can be quite easily monitored by comparing the NMR data of the hydroxy protons.<br/></p>}},
  author       = {{Sandström, Corine and Magnusson, Göran and Nilsson, Ulf and Kenne, Lennart}},
  issn         = {{0008-6215}},
  keywords     = {{Conformation analysis; Galabioside; Hydrogen bonds; Hydroxy protons; NMR; Thioglycoside}},
  language     = {{eng}},
  month        = {{11}},
  number       = {{1-2}},
  pages        = {{46--56}},
  publisher    = {{Elsevier}},
  series       = {{Carbohydrate Research}},
  title        = {{Comparative <sup>1</sup>H NMR study of hydroxy protons in galabioside and its S-linked 4-thiodisaccharide analogue in aqueous solution}},
  url          = {{http://dx.doi.org/10.1016/S0008-6215(99)00215-3}},
  doi          = {{10.1016/S0008-6215(99)00215-3}},
  volume       = {{322}},
  year         = {{1999}},
}