Chirality and fragrance chemistry: stereoisomers of the commercial chiral odorants Muguesia and Pamplefleur.
[structure: see text] The work describes the enzyme-mediated preparation and the odor evaluation of the single stereoisomers of the commercial odorants Muguesia and Pamplefleur. The synthetic approach to Muguesia stereoisomers helped to clear the assignment of the relative configuration of intermediate diols 5. The odor response of Pamplefleur isomers was found to be rather unusual. No stereoisomer prevailed, but each one played a definite role in establishing the odor sensation of the final blend.
Abate
Agnese
A
Dipartimento di Chimica, Materiali ed Ingegneria Chimica del Politecnico, Istituto CNR per la Chimica del Riconoscimento Molecolare, Via Mancinelli 7, I-20131 Milano, Italy.
Brenna
Elisabetta
E
Fuganti
Claudio
C
Gatti
Francesco G
FG
Giovenzana
Tommaso
T
Malpezzi
Luciana
L
Serra
Stefano
S
D000440:Butanols / Q000138:chemical synthesis* / Q000494:pharmacology; D018360:Crystallography, X-Ray; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015394:Molecular Structure; D009812:Odorants; D012903:Smell / Q000187:drug effects; D013237:Stereoisomerism
D000440:Butanols; C500278:Muguesia; C500276:Pamplefleur