Oligomers and peptidomimetics consisting of methyl 3-amino-2,3-dideoxyhexopyranosiduronic acids
Emilia Sikorska , Dorota Tuwalska , Przemysław Karpowicz , Elżbieta Jankowska , Andrzej Nowacki , Beata Liberek
AbstractIn 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.
|Journal series||Tetrahedron, ISSN 0040-4020, (A 30 pkt)|
|Publication size in sheets||0.55|
|Keywords in English||sugar amino acid, conformation, MD simulations, CD spectra, proteasome|
|ASJC Classification||; ;|
|Score|| = 30.0, 24-07-2019, ArticleFromJournal|
= 30.0, 24-07-2019, ArticleFromJournal
|Publication indicators||= 2; : 2015 = 0.84; : 2015 = 2.645 (2) - 2015=2.621 (5)|
|Citation count*||3 (2020-02-14)|
* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or Perish system.