Premium
Trapping of Organophosphorus Chemical Nerve Agents in Water with Amino Acid Functionalized Baskets
Author(s) -
Ruan Yian,
Dalkiliç Erdin,
Peterson Paul W.,
Pandit Aroh,
Dastan Arif,
Brown Jason D.,
Polen Shane M.,
Hadad Christopher M.,
Badjić Jovica D.
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201304779
Subject(s) - substituent , steric effects , chemistry , branching (polymer chemistry) , aqueous solution , dimethyl methylphosphonate , phosphate buffered saline , nerve agent , organic chemistry , polymer chemistry , chromatography , acetylcholinesterase , enzyme
We prepared eleven amino‐acid functionalized baskets and used 1 H NMR spectroscopy to quantify their affinity for entrapping dimethyl methylphosphonate (DMMP, 118 Å 3 ) in aqueous phosphate buffer at pH=7.0±0.1; note that DMMP guest is akin in size to chemical nerve agent sarin (132 Å 3 ). The binding interaction ( K a ) was found to vary with the size of substituent groups at the basket′s rim. In particular, the degree of branching at the first carbon of each substituent had the greatest effect on the host‐guest interaction, as described with the Verloop′s B1 steric parameter. The branching at the remote carbons, however, did not perturb the encapsulation, which is important for guiding the design of more effective hosts and catalysts in future.