Non-empirical assignment of the absolute configuration of (-)-naringenin, by coupling the exciton analysis of the circular dichroism spectrum and the ab initio calculation of the optical rotatory power.
The non-empirical assignment of the absolute configuration of (-)-naringenin, the aglycone of (-)-naringin, a flavanone glycoside abundant in the albedo of immature grapefruits and showing several interesting biological properties, has been approached by two different methods: (a) the exciton analysis of the circular dichroism (CD) spectrum and (b) the ab initio calculation of the optical rotatory power. Both the methods indicate the configurational correlation (-)/(S), as empirically suggested by Gaffield. A comparison of advantages and limitations of the two methods of analysis is also presented.
Giorgio
Egidio
E
Dipartimento di Chimica, Università della Basilicata, via N. Sauro 85, 85100, Potenza, Italy.
Parrinello
Nunziatina
N
Caccamese
Salvatore
S
Rosini
Carlo
C
D002942:Circular Dichroism; D044950:Flavanones / Q000737:chemistry* / Q000302:isolation & purification; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D009904:Optical Rotation; D013237:Stereoisomerism
D044950:Flavanones; C005273:naringenin