BIOSYNTHESIS OF ANOSMINE - INCORPORATION OF THE INTACT 6-CARBON CHAINOF LYSINE AND OF PIPECOLIC ACID

Label from DL-[1,2-C-13(2)]lysine enters the two carbon atoms, C-7 and C-6, of the orchid alkaloids anosmine [6] as an intact C-2 unit. This result provides further evidence for the derivation of the alkaloid f rom two molecules of lysine [1). One of these lysine units enters via cadaverine [3] and DELTA1-piperideine [5), supplying the C5N-unit, C-1 3 to C-9,N-8, of anosmine, while the other generates the fragment, N-1 ,C-2 to C-7, by providing a C6N-chain, which enters by way of pipecoli c acid [4], since C-13 from DL-[carboxyl-C-13,(RS)-6-H-2(1)]pipecolic acid is incorporated into C-7 of the alkaloid. The complete assignment of the signals in the H-1 and C-13 spectra of the alkaloid is discuss ed.