Absolute configuration of anabasine from Messor and Aphaenogaster ants

Citation
S. Leclercq et al., Absolute configuration of anabasine from Messor and Aphaenogaster ants, J CHEM ECOL, 27(5), 2001, pp. 945-952
Citations number
15
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Environment/Ecology
Journal title
JOURNAL OF CHEMICAL ECOLOGY
ISSN journal
0098-0331 → ACNP
Volume
27
Issue
5
Year of publication
2001
Pages
945 - 952
Database
ISI
SICI code
0098-0331(200105)27:5<945:ACOAFM>2.0.ZU;2-X
Abstract
A method has been developed to assign the absolute configuration and enanti omeric excess of anabasine based on small amounts of material (in the micro gram range), by derivatization with (+)-menthylchloroformate followed by ca pillary GC analysis of the resulting carbamate(s). This method was applied to three samples of anabasine isolated from Messor and Aphaenogaster ants. In Messor sanctus, only (2'S)-anabasine was present, whereas in Aphaenogast er subterranea and A. miamiana (2'S)-anabasine was determined to have an ee of 78 and 24%, respectively.