14 



Aromatic Compounds Not Classified 

 Elsewhere 



This chapter includes a heterogeneous group of aromatic 

 compounds which arise from different biosynthetic routes. Cin- 

 namic acid and its derivatives undoubtedly are formed by way 

 of the shikimic acid pathway.^' ^ The occurrence of anisalde- 

 hyde and anisic acid derivatives in the same fermentation with 

 methyl p-methoxycinnamate suggests that the former may be 

 degradation products of the latter. 



Chloramphenicol, too, has a Ce-Ca skeleton which seems to 

 relate it to the shikimic acid pathway. It has been shown that 

 p-nitrophenylserinol does not act as a precursor, and, when it is 

 added to fermentations, it is acetylated but not dichloroacety- 

 lated. C"-Labeled p-nitrophenylserinol is not incorporated into 

 the chloramphenicol molecule nor is C"-labeled dichloroacetic 

 acid. Thus, what appears to be a logical step in the biosynthe- 

 sis — the dichloroacetylation of p-nitrophenylserinol — does not 

 occur.^ 



The tricarboxylic acid produced by Chaetomium indicum is 

 evidently formed by the condensation of a-ketoglutaric acid with 

 phenylpyruvic acid. 



The lichen acids of this chapter show a provocative symme- 

 try, and the incorporation of amino acids into two of them is in- 

 teresting. The diphenylbutadiene structure has been found 

 also in xanthocillin. Apparently there has been no experimen- 

 tal study of their biogenesis. 



^ Friedrich Weygand and Heinz Wendt, Z. Natiirforsch. 14b 421 

 (1959). 



2T. A. Geissman and T. Swain, Chem. and Ind., 984 (1957). 



3 David Gottlieb, P. W. Robbins and H. E. Carter, J. Bacterial. 72 

 153 (1956). 



