MD-based CD calculations for the assignment of the absolute axial configuration of the naphthylisoquinoline alkaloid dioncophylline A

The circular dichroism (CD) of the biaryl alkaloid dioncophylline A (2) was investigated by CD calculations; the structures were generated by molecular dynamics (MD) simulations using the force field CVFF. From these structures the CD spectra were calculated with the semiempirical method CNDO/2S. Su...

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Published inJournal of computational chemistry Vol. 22; no. 12; pp. 1273 - 1278
Main Authors Bringmann, Gerhard, Mühlbacher, Jörg, Repges, Charlotte, Fleischhauer, Jörg
Format Journal Article
LanguageEnglish
Published New York John Wiley & Sons, Inc 01.09.2001
Subjects
biaryl alkaloids
circular dichroism calculations
CNDO/2S
molecular dynamics simulations
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Summary:The circular dichroism (CD) of the biaryl alkaloid dioncophylline A (2) was investigated by CD calculations; the structures were generated by molecular dynamics (MD) simulations using the force field CVFF. From these structures the CD spectra were calculated with the semiempirical method CNDO/2S. Summing up the single CD spectra yielded the final spectrum. In contrast to our earlier method based on the Boltzmann weighting, the MD‐assisted approach permitted to assign the flexible biaryl axis of dioncophylline A (2), which is found to be P. © 2001 John Wiley & Sons, Inc. J Comput Chem 22: 1273–1278, 2001
Bibliography:ArticleID:JCC1084
Bundesministerium für Bildung, Wissenschaft und Forschung
ark:/67375/WNG-6N8T2RDZ-0
Fonds der Chemischen Industrie - No. Fl 142/3-3
DFG
istex:C74EA9EFDB41EDCA9FF85ECDCA2E7A754AEAC5DF
ISSN:0192-8651
1096-987X
DOI:10.1002/jcc.1084