Federwisch, G. and Kleinmaier, R. and Drettwan, D. and Gschwind, R. M. (2008) The H-Bonding Network of Acylguanidine Complexes: Combined Intermolecular 2hJH,P and 3hJN,P Scalar Couplings Provide an Insight into the Geometric Arrangement. Journal of the American Chemical Society 130 (50), pp. 16846-16847.
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The H-bonding networks of arginines and acylguanidines are crucial for many biological and pharmaceutical interactions. However, the effect of acylation of guanidines on the binding mode and the H-bond strengths has not yet been explored in solution. Therefore, the H-bonding network of a 15N labeled acylguanidine derivative in a bisphosphonate arginine receptor is investigated. The direct NMR detection of 1D, 2D, and 3D correlations caused by 2hJH,P and, for the first time in nonbiomacromolecules, 3hJN,P couplings, allows for the geometric analysis of the H-bonding network and indicates an end-on binding mode with two different POH angles. The acylguanidine adopts the same binding mode as the corresponding guanidine but forms significantly stronger H-bonds. This may explain the success of acylguanidine ligands in medicinal chemistry applications.
|Institutions:||Chemistry and Pharmacy > Institut für Organische Chemie > Arbeitskreis Prof. Dr. Ruth Gschwind|
|Projects:||GRK 760, Graduiertenkolleg Medizinische Chemie|
|Subjects:||500 Science > 540 Chemistry & allied sciences|
|Refereed:||Yes, this version has been refereed|
|Created at the University of Regensburg:||Yes|
|Deposited On:||11 Nov 2009 15:32|
|Last Modified:||11 Nov 2009 15:32|