Comparative 1H NMR study of hydroxy protons in galabioside and its S-linked 4-thiodisaccharide analogue in aqueous solution
(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
- Sandström, Corine ; Magnusson, Göran LU ; Nilsson, Ulf LU and Kenne, Lennart
- organization
- publishing date
- 1999-11-23
- 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}}, }