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The importance of orientation of exocyclic groups in a naphthoxyloside: A specific rotation calculation study
Stockholm University, Faculty of Science, Department of Organic Chemistry.ORCID iD: 0000-0001-8303-4481
Number of Authors: 3
2017 (English)In: Journal of Physical Organic Chemistry, ISSN 0894-3230, E-ISSN 1099-1395, Vol. 30, no 12, e3708Article in journal (Refereed) Published
Abstract [en]

2-Naphthyl -d-xylopyranoside (XylNap) inhibits -1,4-galactosyltransferase 7 (4GalT7) and thereby growth of tumor cells both in vitro and in vivo. The binding pocket of 4GalT7 has a defined orientation of hydrogen bond acceptors and hydrophobic moiety. Knowing the orientation of the hydroxyl and naphthyl groups of this molecule would help in the development of more efficient inhibitors. In this work, we have tried, for the first time, to determine the exocyclic hydroxyl and aglycon groups orientation of XylNap, using ab initio descriptions, and calculation of the specific rotation values, in methanol solutions, using 2 different solvent descriptions: a dielectric continuum approach (polarizable continuum model [PCM]) and a microsolvated+continuum approach (MS+PCM). In the PCM approach, [](D)=-59 deg/(dm(g/cm(3))) whereas for the MS+PCM approach [](D)=-29 deg/(dm(g/cm(3))). The latter is in excellent agreement with the experimentally determined value in methanol solution, viz, [](D)=-30 deg/(dm(g/cm(3))). This agreement allows us to say that the hydroxyl groups have similar orientations in xylose and XylNap, and the naphthyl group has a very well-defined dihedral angle value in the most abundant conformations.

Place, publisher, year, edition, pages
2017. Vol. 30, no 12, e3708
Keyword [en]
naphthyl xylose, specific rotation, xylopyranose
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-150061DOI: 10.1002/poc.3708ISI: 000415357800015OAI: oai:DiVA.org:su-150061DiVA: diva2:1165003
Available from: 2017-12-12 Created: 2017-12-12 Last updated: 2017-12-12Bibliographically approved

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