Determination of the enantiomeric purity of the phytoalexins spirobrassinins by 1H NMR using chiral solvation.
A simple and inexpensive method for enantiomeric discrimination of the phytoalexins spirobrassinin (1), 1-methoxyspirobrassinin (2) and synthetic analog 1-methylspirobrassinin (6) using the chiral solvating agent 2,2,2-trifluoro-1-(9-anthryl)ethanol in C(6)D(6) is described. Using this method the enantiomeric composition of each sample can be determined accurately by (1)H NMR and the compounds can be recovered readily by chromatography.
Department of Chemistry, University of Saskatchewan, 110 Science Place, Saskatoon, Saskatchewan, Canada S7N 5C9. s.pedras@usask.ca
M S C
MS
Pedras
M
M
Hossain
M G
MG
Sarwar
S
S
Montaut
D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008968:Molecular Conformation; D010936:Plant Extracts / Q000737:chemistry*; D012717:Sesquiterpenes; D012997:Solvents / Q000737:chemistry; D013141:Spiro Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D013729:Terpenes; D013844:Thiazoles / Q000737:chemistry*; D000094162:Phytoalexins
C497735:1-methoxyspirobrassinin; D010936:Plant Extracts; D012717:Sesquiterpenes; D012997:Solvents; D013141:Spiro Compounds; D013729:Terpenes; D013844:Thiazoles; C497736:phytoalexin spirobrassinin; C417935:spirobrassinin; D000094162:Phytoalexins