Change search
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf
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
2017 (English)In: Journal of Physical Organic Chemistry, ISSN 0894-3230, E-ISSN 1099-1395, Vol. 30, no 12, article id 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
John Wiley & Sons, 2017. Vol. 30, no 12, article id e3708
Keywords [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, id: diva2:1165003
Funder
Swedish Research Council
Note

Open Access 2019-12-01

Available from: 2017-12-12 Created: 2017-12-12 Last updated: 2019-09-06Bibliographically approved

Open Access in DiVA

fulltext(652 kB)44 downloads
File information
File name FULLTEXT01.pdfFile size 652 kBChecksum SHA-512
c15bd597f14b0eb8439c2732b9bab76fdc9c4a5521503363780eb1b4357605f6053ae424ff39cd67fbc8d8695dae5470a2f36b71830a6f580d965aee32076110
Type fulltextMimetype application/pdf

Other links

Publisher's full text

Search in DiVA

By author/editor
Widmalm, Göran
By organisation
Department of Organic Chemistry
In the same journal
Journal of Physical Organic Chemistry
Organic Chemistry

Search outside of DiVA

GoogleGoogle Scholar
Total: 44 downloads
The number of downloads is the sum of all downloads of full texts. It may include eg previous versions that are now no longer available

doi
urn-nbn

Altmetric score

doi
urn-nbn
Total: 91 hits
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf