Synthesis, chiral HPLC resolution and configuration assignment of 1-phenylglyceryl trinitrate stereomers.
As an introductory study of in vitro vasodilating activity, the access to the four stereomers of 1-phenylglyceryl trinitrate is described using achiral and chiral chromatography. For semi-preparative separation of the enantiomers, a Chiralcel OD (250 x 10 mm, 10 microm) was used. Catalytic reduction leading to the corresponding stereomers of 1-phenylglycerol allowed absolute configuration assignments. The same methods were used for the separation and configuration assignment of the enantiomers of 3-phenylpropane-1,2-diyl dinitrate.
Chegaev
Konstantin
K
Dipartimento di Scienza e Tecnologia del Farmaco, Università degli Studi di Torino, Torino, Italy.
Lazzarato
Loretta
L
Tron
Gian Cesare
GC
Marabello
Domenica
D
Stilo
Antonella Di
AD
Cena
Clara
C
Fruttero
Roberta
R
Gasco
Alberto
A
Vanthuyne
Nicolas
N
Roussel
Christian
C
D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D008956:Models, Chemical; D015394:Molecular Structure; D005996:Nitroglycerin / Q000032:analysis* / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014665:Vasodilator Agents / Q000032:analysis* / Q000138:chemical synthesis* / Q000737:chemistry
D014665:Vasodilator Agents; D005996:Nitroglycerin