Premium
Isolierung von (2 S , 4 S )‐(+)‐γ‐Hydroxynorvalin und (2 S , 4 R )‐(−)‐γ‐Hydroxynorvalin aus Boletus satanas Lenz
Author(s) -
Matzinger P.,
Catalfomo Ph.,
Eugster C. H.
Publication year - 1972
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19720550513
Subject(s) - chemistry , diastereomer , stereochemistry , optically active , chirality (physics) , boletus , organic chemistry , chiral symmetry , mushroom , food science , physics , quantum mechanics , nambu–jona lasinio model , quark
We have isolated from the carpophores of Boletus satanas Lenz ( Basidiomycetae ) (2 S ,4 S )‐(+)‐γ‐hydroxynorvaline ( 1 ) and (2 S ,4 R )‐(−)‐γ‐hydroxynorvaline ( 2 ). The chirality of each diastereomer has been determined by chemical synthesis starting from optically active precursors and by application of different chiroptical methods. Gaschromatographic separation of the derived diastereomeric N‐[( S )‐α‐methoxypropionyl]‐lactones reveals that the optical purity of natural 2 is 88% whereas 1 exists as a partial racemate: (2 S ,4 S ): (2 R ,4 R ) = 3:2. Muscarine could not be detected in the carpophores of B. satanas , contrary to some literature data but basic substances of unknown structure are present in low concentration.