Oligomers and peptidomimetics consisting of methyl 3-amino-2,3-dideoxyhexopyranosiduronic acids

Emilia Sikorska , Dorota Tuwalska , Przemysław Karpowicz , Elżbieta Jankowska , Andrzej Nowacki , Beata Liberek

Abstract

In search of new foldamers, the synthesis of homo and heterooligomeric tetramers, consisting of methyl 3-amino-2,3-dideoxyhexopyranosiduronic acids, from the respective dimers, is presented. Both the dimers and tetramers were subjected to molecular dynamics simulations, based on NOE interactions. These show the preferred conformations of presented sugar amino acids (SAAs) oligomers. The CD spectra of these oligomers depend on the configuration of the C3 carbon atom bearing the amide chromophore. Next, the syntheses of two peptidomimetics with SAA incorporated into a peptide chain, are presented. A Leu-enkephalin mimetic was subjected to molecular dynamics simulations, which show how a SAA influences the geometry of a peptidomimetic. A Tat1 protein mimetic is demonstrated to display an inhibitory influence on the activity of a proteasome. Its structure is studied on a basis of the CD and FTIR spectra.
Author Emilia Sikorska (FCh / DOCh / LChB)
Emilia Sikorska,,
- Laboratory of Chemistry of Biopolymers
, Dorota Tuwalska
Dorota Tuwalska,,
-
, Przemysław Karpowicz (FCh / DBCh / LMCh)
Przemysław Karpowicz ,,
- Laboratory of Medical Chemistry
, Elżbieta Jankowska (FCh / DBCh / LMCh)
Elżbieta Jankowska,,
- Laboratory of Medical Chemistry
, Andrzej Nowacki (FCh / DOCh / LG)
Andrzej Nowacki,,
- Laboratory of Glycochemistry
, Beata Liberek (FCh / DOCh / LG)
Beata Liberek,,
- Laboratory of Glycochemistry
Journal seriesTetrahedron, ISSN 0040-4020, (A 30 pkt)
Issue year2015
Vol71
No13
Pages2013-2024
Publication size in sheets0.55
Keywords in Englishsugar amino acid, conformation, MD simulations, CD spectra, proteasome
DOIDOI:10.1016/j.tet.2015.02.009
URL http://dx.doi.org/10.1016/j.tet.2015.02.009
Languageen angielski
Score (nominal)30
ScoreMinisterial score = 30.0, 20-12-2017, ArticleFromJournal
Ministerial score (2013-2016) = 30.0, 20-12-2017, ArticleFromJournal
Publication indicators WoS Impact Factor: 2015 = 2.645 (2) - 2015=2.621 (5)
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