Dependence of pyranose ring puckering on anomeric configuration: methyl idopyranosides.

The Journal of Physical Chemistry. B
Benedict M SattelleAndrew Almond

Abstract

In the aldohexopyranose idose, the unique presence of three axial ring hydroxyl groups causes considerable conformational flexibility, rendering it challenging to study experimentally and an excellent model for rationalizing the relationship between puckering and anomeric configuration. Puckering in methyl α- and β-L-idopyranosides was predicted from kinetically rigorous 10 μs simulations using GLYCAM11 and three explicit water models (TIP3P, TIP4P, and TIP4P-EW). In each case, computed pyranose ring three-bond (vicinal) (1)H-(1)H spin couplings ((3)J(H,H)) trended with NMR measurements. These values, calculated puckering exchange rates and free energies, were independent of the water model. The α- and β-anomers were (1)C(4) chairs for 85 and >99% of their respective trajectories and underwent (1)C(4)→(4)C(1) exchange at rates of 20 μs(-1) and 1 μs(-1). Computed α-anomer (1)C(4)↔(4)C(1) puckering rates depended on the exocyclic C6 substituent, comparing hydroxymethyl with carboxyl from previous work. The slower kinetics and restricted pseudorotational profile of the β-anomer were caused by water occupying a cavity bounded by the anomeric 1-O-methyl and the C6 hydroxymethyl groups. This finding rationalizes the different methyl ...Continue Reading

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Citations

Feb 27, 2013·Biomacromolecules·Benedict M SattelleAndrew Almond
Oct 8, 2014·Journal of Chemical Information and Modeling·Spandana MakeneniRobert J Woods
Dec 3, 2014·Carbohydrate Research·Xiuming XiongJiye Shi
Mar 22, 2014·Physical Chemistry Chemical Physics : PCCP·Benedict M Sattelle, Andrew Almond
Jan 5, 2013·The Journal of Physical Chemistry. B·Pavel OborskýVojtěch Spiwok
Dec 23, 2016·The Journal of Organic Chemistry·Bidisha Bose-BasuAnthony S Serianni
Jul 26, 2017·Physical Chemistry Chemical Physics : PCCP·Karolina Gaweda, Wojciech Plazinski
Jul 1, 2017·Chemistry : a European Journal·Daniel MatznerGünter Mayer
May 14, 2019·Wiley Interdisciplinary Reviews. Computational Molecular Science·Balaji NagarajanUmesh R Desai
Jun 13, 2017·Canadian Journal of Chemistry·Arunima SinghRobert J Woods
Mar 21, 2018·The Journal of Physical Chemistry. B·Karina PanczykWojciech Plazinski
Nov 13, 2012·Journal of Chemical Theory and Computation·Karl N KirschnerThereza A Soares
Aug 15, 2019·Journal of Chemical Theory and Computation·Poonam PandeySairam S Mallajosyula

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