Absolute configuration of anabasine from Messor and Aphaenogaster ants.
A method has been developed to assign the absolute configuration and enantiomeric excess of anabasine based on small amounts of material (in the microgram range), by derivatization with (+)-menthylchloroformate followed by capillary 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 Aphaenogaster subterranea and A. miamiana (2'S)-anabasine was determined to have an ee of 78 and 24%, respectively.
Leclercq
S
S
Department of Organic Chemistry, Free University of Brussels, Belgium.
Charles
S
S
Daloze
D
D
Braekman
J C
JC
Aron
S
S
Pasteels
J M
JM
D000691:Anabasine / Q000032:analysis / Q000737:chemistry*; D000818:Animals; D001000:Ants / Q000737:chemistry*; D002849:Chromatography, Gas; D007306:Insecticides / Q000032:analysis / Q000737:chemistry*; D010944:Plants
D007306:Insecticides; D000691:Anabasine