Confirmation of the structure of (3S)-3-hydroxyquinine: synthesis and X-ray crystal structure of its 9-aceto analogue.
3(S)-3-Hydroxyquinine (2) has been separated from its epimeric mixture at C-3 by conversion into the 9-aceto analogue followed by chromatography. The molecular structure of the acetate was determined through single-crystal X-ray analysis, and this confirms the structure of (3S)-3-hydroxyquinine (2), the major metabolite of quinine (1).
Department of Chemistry, University of Wisconsin-Milwaukee, Milwaukee, 53201, USA.
P V V
PV
Srirama Sarma
Dongmei
D
Han
Jefferey R
JR
Deschamps
James M
JM
Cook
D018360:Crystallography, X-Ray; D008968:Molecular Conformation; D015394:Molecular Structure; D011802:Quinidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry*; D011803:Quinine / Q000737:chemistry; D013237:Stereoisomerism
C013569:3-hydroxyquinidine; D011803:Quinine; D011802:Quinidine