dc.contributor.author
Salta, Joana
dc.contributor.author
Dernedde, Jens
dc.contributor.author
Reissig, Hans-Ulrich
dc.date.accessioned
2018-06-08T02:52:00Z
dc.date.available
2015-06-01T06:24:07.065Z
dc.identifier.uri
https://refubium.fu-berlin.de/handle/fub188/14023
dc.identifier.uri
http://dx.doi.org/10.17169/refubium-18220
dc.description.abstract
In this article a series of divalent and trivalent carbohydrate mimetics on
the basis of an enantiopure aminopyran and of serinol is described. These
aminopolyols are connected by amide bonds to carboxylic acid derived spacer
units either by Schotten–Baumann acylation or by coupling employing HATU as
reagent. The O-sulfation employing the SO3·DMF complex was optimized. It was
crucial to follow this process by 700 MHz 1H NMR spectroscopy to ensure full
conversion and to use a refined neutralization and purification protocol. Many
of the compounds could not be tested as L-selectin inhibitor by SPR due to
their insolubility in water, nevertheless, a divalent and a trivalent amide
showed surprisingly good activities with IC50 values in the low micromolar
range.
de
dc.rights.uri
http://creativecommons.org/licenses/by/2.0/
dc.subject
carbohydrate mimetics
dc.subject
carboxylic acid amides
dc.subject.ddc
500 Naturwissenschaften und Mathematik::540 Chemie
dc.title
Synthesis of multivalent carbohydrate mimetics with aminopolyol end groups and
their evaluation as L-selectin inhibitors
dc.type
Wissenschaftlicher Artikel
dcterms.bibliographicCitation
Beilstein Journal of Organic Chemistry. - 11 (2015), S. 638–646
dcterms.bibliographicCitation.doi
10.3762/bjoc.11.72
dcterms.bibliographicCitation.url
http://www.beilstein-journals.org/bjoc/single/articleFullText.htm?publicId=1860-5397-11-72
refubium.affiliation
Biologie, Chemie, Pharmazie
de
refubium.affiliation.other
Institut für Chemie und Biochemie
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refubium.mycore.fudocsId
FUDOCS_document_000000022472
refubium.note.author
Der Artikel wurde in einer Open-Access-Zeitschrift publiziert.
refubium.resourceType.isindependentpub
no
refubium.mycore.derivateId
FUDOCS_derivate_000000004941
dcterms.accessRights.openaire
open access