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Structural Modifications of cis ‐Glycofused Benzopyran Compounds and Their Influence on the Binding to Amyloid‐β Peptide
Author(s) -
Airoldi Cristina,
D'Orazio Giuseppe,
Richichi Barbara,
Guzzi Cinzia,
Baldoneschi Veronica,
Colombo Laura,
Salmona Mario,
Nativi Cristina,
Nicotra Francesco,
La Ferla Barbara
Publication year - 2016
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201501114
Subject(s) - chemistry , peptide , molecular dynamics , ring (chemistry) , benzopyran , stereochemistry , nuclear magnetic resonance spectroscopy , pyran , molecular mechanics , crystallography , biophysics , computational chemistry , biochemistry , organic chemistry , biology
A small library of glycofused tricyclic compounds with a central pyran ring chemically modified in the position para to the ring oxygen has been synthesised. The influence of the chemical modification on the structural conformation of the compounds and on their ability to bind Aβ peptide has been evaluated respectively using molecular mechanics (MM) and molecular dynamics (MD) simulations, and STD NMR spectroscopy. The introduction of particularly polar/charged groups leads to the loss of binding ability, without a significant change in the conformation, whilst other substitutions does not significantly affect either the structural conformation or the binding.