Premium
Quantum Mechanical Calculation of Coupling Constants in the Configurational Analysis of Flexible Systems: Determination of the Configuration of Callipeltin A
Author(s) -
Bassarello Carla,
Zampella Angela,
Monti Maria Chiara,
GomezPaloma Luigi,
D’Auria Maria Valeria,
Riccio Raffaele,
Bifulco Giuseppe
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500740
Subject(s) - chemistry , coupling constant , quantum chemical , antifungal , residue (chemistry) , quantum , coupling (piping) , computational chemistry , amino acid residue , stereochemistry , organic chemistry , molecule , quantum mechanics , mechanical engineering , physics , medicine , biochemistry , dermatology , engineering , peptide sequence , gene
An integrated NMR‐quantum mechanical (QM) approach, relying on the comparison between calculated and experimental J ‐values, was applied to the analysis of the relative configuration of four amino acid units (known as AGDHE, D ‐ a Thr1, D ‐ a Thr2 and β‐OMeTyr) contained in callipeltin A, a cyclopeptide endowed with a powerful inhibitory activity on the cardiac sodium/calcium exchanger and also showing interesting antiviral and antifungal properties. In this paper we report the first example of the application of this method to a real case, which allowed the assignment of the relative configuration of the β‐OMeTyr residue and the revision of the configuration of the Thr2 unit in callipeltin A. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)