Why a diaminopyrrolic tripodal receptor binds mannosides in acetonitrile but not in water?

• Diogo Vila-Viçosa,
• Oscar Francesconi and
• Miguel Machuqueiro

Beilstein J. Org. Chem. 2014, 10, 1513–1523, doi:10.3762/bjoc.10.156

• : conformational analysis; constant-pH MD; mannose; multivalent glycosystems; pH; synthetic receptor; Introduction The recognition of specific carbohydrates is an important step in several biological processes [1]. To better understand these recognition processes, several synthetic receptors have been developed

• ][18][19][20][21][22][23][24]. Since MD simulations deal with pH in a limited way, simply by setting a fixed protonation state in the beginning of the simulation, the use of one of these methods is mandatory. The stochastic titration constant-pH MD method [15][21] takes advantage from the

• structure [39][40]. In this work, we performed an exhaustive conformational study of a chiral diaminopyrrolic tripodal receptor (Figure 1) in both water and acetonitrile. We used MM/MD simulations in the organic solvent and constant-pH MD to simulate the receptor in water at several pH values. Moreover, the