Dr John Sanderson j.m.sanderson@durham.ac.uk
Associate Professor
Refined models for the preferential interactions of tryptophan with phosphocholines
Sanderson, J.M.
Authors
Abstract
series of molecular models of the adducts formed between N-acetyl-L-tryptophan ethylamide and diacetyl-sn-glycero-3-phosphocholine have been generated. Using rOesy data that enabled us to place restrictions on the proximity of a number of key protons in the amino acid/phosphocholine pairs, a series of structures were generated following molecular dynamics and mechanics experiments using the CHARMM27 force field. These structures were then subjected to a series of clustering algorithms in order to classify the tight binding interactions between a single tryptophan and a phosphocholine. From these analyses, it is evident that: (i) binding is characterised by hydrogen bonding between the indole NH as donor and phosphate oxygen as acceptor, cation–carbonyl interactions between the choline ammonium and amide carbonyl groups and cation– interactions; (ii) cation– interactions are not always observed, particularly when their formation is at the expense of cation–carbonyl and hydrogen bonding interactions; (iii) on the basis of amino acid torsional parameters, it is possible to predict whether the phosphocholine headgroup will bind in a compact or elongated conformation. Extension of the procedures to characterise 2 : 1 Trp–PC binding revealed that the same intermolecular interactions are predominant; however, combinations of all three intermolecular interactions within the same adduct occur much more frequently due to the availability of donor/acceptor groups from both tryptophans in the 2 : 1 system.
Citation
Sanderson, J. (2007). Refined models for the preferential interactions of tryptophan with phosphocholines. Organic and Biomolecular Chemistry, 5(20), 3276- 3286. https://doi.org/10.1039/b707502b
Journal Article Type | Article |
---|---|
Publication Date | Jan 1, 2007 |
Deposit Date | Jan 17, 2008 |
Journal | Organic and Biomolecular Chemistry |
Print ISSN | 1477-0520 |
Electronic ISSN | 1477-0539 |
Publisher | Royal Society of Chemistry |
Peer Reviewed | Peer Reviewed |
Volume | 5 |
Issue | 20 |
Pages | 3276- 3286 |
DOI | https://doi.org/10.1039/b707502b |
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