Premium
Identification of degradants of a complex alkaloid using NMR cryoprobe technology and ACD/structure elucidator
Author(s) -
Martin Gary E.,
Hadden Chad E.,
Russell David J.,
Kaluzny Brian D.,
Guido Jane E.,
Duholke Wayne K.,
Stiemsma Bruce A.,
Thamann Thomas J.,
Crouch Ronald C.,
Blinov Kirill,
Elyashberg Mikhail,
Martirosian Eduard R.,
Molodtsov Sergey G.,
Williams Antony J.,
Schiff Paul L.
Publication year - 2002
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570390619
Subject(s) - chemistry , alkaloid , chemical structure , chromatography , proton nmr , degradation (telecommunications) , molecule , organic chemistry , telecommunications , computer science
Identification of degradants of pharmaceuticals is a necessary challenge of the drug development process following the subjection of candidate molecules to a variety of physico‐chemical stresses. It would be desirable to be able to conduct such studies on a minimal amount of material. As a prototypical study, the isolation and identification of degradants of a sample of the complex indoloquinoline alkaloid, cryptospirolepine, was undertaken after prolonged storage in DMSO solution using a combination of cryogenic NMR probe technology and CASE (Computer‐Assisted Structure Elucidation) programs. None of the starting alkaloid remained after storage; a chromatogram of the DMSO solution demonstrated the presence of >25 components in the mixture. The two most abundant degradation products were identified as the known alkaloid cryptolepinone (∼35%) and an unprecedented rearrangement product, DP‐2, (∼16%).