onr:"swepub:oai:DiVA.org:su-24631"
Search: onr:"swepub:oai:DiVA.org:su-24631" > Conformational anal...
- 1 of 1
- Previous record
- Next record
- To hitlist
Conformational analysis of β-linked glucobiosides based on hetero- and homonuclear couplings across the glycosidic linkage
-
- Olsson, Ulrika (author)
- Stockholms universitet,Institutionen för organisk kemi
- Serianni, Anthony S. (author)
- Stenutz, Roland (author)
- (creator_code:org_t)
- 2008-03-18
- 2008
- English.
- In: Journal of Physical Chemistry B. - : American Chemical Society (ACS). - 1520-6106 .- 1520-5207. ; 112:14, s. 4447-4453
- Journal article (peer-reviewed)
Abstract
Subject headings
Close
- Four β-linked glucobioses selectively 13C labeled at C1‘ or C2‘ have been prepared. The inter-residue coupling constants, JCH, and JCC, have been determined and related to the solution conformations of the disaccharides using Karplus-type relationships. Relying only on the experimental coupling constants, glycosidic linkage conformation in methyl α-sophoroside (methyl 2-O-β-d-glucopyranosyl-α-d-glucopyranoside), methyl α-laminarabioside (methyl 3-O-β-d-glucopyranosyl-α-d-glucopyranoside), and methyl α-cellobioside (methyl 4-O-β-d-glucopyranosyl-α-d-glucopyranoside) were found to be close to those observed in the solid state (39° < H < 41°, −24° < ψH < −36°). The laminarabioside and cellobioside were found to have conformations that accommodate an intramolecular hydrogen bond to O5‘ that is observed in the solid state. In all compounds, the exocyclic hydroxymethyl groups retain a conformation close to that observed in unsubstituted glucose (gt/gg 1:1). Methyl α-gentiobioside (methyl 6-O-β-d-glucopyranosyl-α-d-glucopyranoside) shows greater flexibility at the ψ-torsion than the other disaccharides, but the population distribution around the C5−C6 bond is essentially unaffected by substitution. None of the O2‘ hydroxyl groups of the β-d-glucopyranosyl residues in any of the disaccharides appear to be involved in inter-residue hydrogen bonding since 1JCH, 1JCC, and 2JCH values sensitive to C2‘−O2‘ rotamer distribution remain close to those observed in methyl β-d-glucopyranoside.
Subject headings
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
Keyword
- Organic chemistry
- Organisk kemi
Publication and Content Type
- ref (subject category)
- art (subject category)
Find in a library
- Journal of Physical Chemistry B (Search for host publication in LIBRIS)
To the university's database
- 1 of 1
- Previous record
- Next record
- To hitlist
Find more in SwePub
- By the author/editor
- Olsson, Ulrika
- Serianni, Anthon ...
- Stenutz, Roland
- About the subject
-
- NATURAL SCIENCES
- NATURAL SCIENCES
- and Chemical Science ...
- and Organic Chemistr ...
- Articles in the publication
- Journal of Physi ...
- By the university
- Stockholm University
Search outside SwePub
- Extend your search to:
- Google Book Search
- Google Scholar
Kungliga biblioteket hanterar dina personuppgifter i enlighet med EU:s dataskyddsförordning (2018), GDPR. Läs mer om hur det funkar här.
Så här hanterar KB dina uppgifter vid användning av denna tjänst.
- Copyright © LIBRIS - National Library Systems
- LIBRIS.kb.se
