The Biosynthesis of Nicotine in Nicotiana glutinosa from Carbon-14 Dioxide

Abstract

the N-methylgroup, and carpon~2' of the pyrrolid'~ri.-~.•:~ihg_wa~.• determined. These data were correlated in terms :Of~•Ji)> the . .

The Biosynthesis of Opium Alkaloids. Reticuline as the Benzyltetrahydroisoquinoline Precursor of Thebaine in Biosynthesis with Carbon-14 Dioxide*

“…The high rate of incorporation of radioactivity into the total alkaloids as well as into thebaine and reticuline both in seedlings and in mature F 1 varlipr work in this laboratory (Rapoport et al, 1960; Stermitz and Rapoport, 1961) established the rapid de novo synthesis of thebaine (I) (Chart I) from 14C02 and its primacy in the hydrophenanthrene alkaloid series. These reports together with similar studies on the biosynthesis of nicotine alkaloids (Alworth et al, 1964;Liebman et al, 1965Liebman et al, , 1967 provide adequate demonstration of the value of the method which involves growing plants in the presence of 14C02 and determining the relative rates and amounts of radioactivity incorporated into different molecules or different portions of the same molecule. Barton and Cohen (1957) earlier suggested the diphenolic alkaloid, reticuline (Ha), as a likely precursor of thebaine (I).…”

Positive Halogen Compounds. X. Solvent Effects in the Reactions of t-Butoxy Radicals

“…VII of "Techniques of Organic Chemistry," A. Weissberger, Ed., Interscience Publishers, Inc., New York, N. Y., 1955. We may extend our discussion to the competition between hydrogen abstraction and /3-scission by constructing an isokinetic temperature plot from the data of Table II as shown in Fig. 4. Here the results are rather more complicated.…”

Gas–Liquid Chromatography of Heterocyclic Compounds

“…The treatment of the solid support with alkali as a method of suppressing acid sites proved very fruitful in separating alkaloids. 16 " 21 The investigation of the Chromatographie behavior of HC (pyridine, furan, thiophene derivatives) on columns packed with the alkali-treated solid support revealed that alkali markedly reduced the solid support specific area, decreased discernibly retention times and effectively eliminated tailing effects in the case of pyridine bases; moreover, alkali participated in the separation process bringing about specific interactions. [22][23][24][25][26][27] In studying the separation of amines and nitrogen-containing HC (pyridine, piperidine, pyrrolidine, pyrrole, picolines), Golovnya et al likewise faced a problem of the specific influence of alkali on the liquid phase properties (polarity increase).…”

“…In particular pyrolysis of some indole alkaloids was performed at 350, 375, and 425°C and the chromatography of the pyrolysis products followed. 16,34 (1964).…”

“…390 They were also the first to perform the synthesis and separation of two isomeric iV-oxides of 4-methylpyridazines, [16] and [17], in comparable conditions. 391 As a means for acquiring knowledge of the nature of pyrimidine derivatives (thymine; cytosine; isocytosine; 2-amino-4-chloro-6-methylpyrimidine; 2,6-dichloro-7-methylpurine; guanine) a method was developed, which was based on pyrolysis of these compounds at 1100-1200°C followed by the Chromatographie analysis of the resulting products at 62 and 75°C.…”