143 



Alicylic Compounds (Non-terpenoid) 



Aldol-like 

 conden- HO 

 sation 



Dehydroquinic 

 Acid 



i 



Quinic Acid 



COOH 



OH 



HO 



Dehydroshikimic 

 Acid 



COOH 



r\/ 



COOH 



HO 



HO 



3,4-Dihydroxy benzoic 

 Acid 



Prephenic 

 Acid 



i 



COOH 



r\/ 



CHoCOCOOH 



NHo 



Anthranilic 

 Acid 



Phenyipyruvic 

 Acid 



Phenylalanine 



Tyrosine 



Tryptophan 



Homogentisic Acid 

 p-Aminobenzoic Acid 

 p-Hydroxybenzoic Acid 



Microorganisms were the principal tools in this work, es- 

 pecially the mold Neiirospora crassa and the bacteria Esch- 

 erichia coli and Aerobacter aerogenes mutated so that the bio- 

 synthesis of aromatic amino acids was blocked at various points. 

 These mutants accumulated intermediates in the sequence prior 

 to the blocks, and these substances could then be isolated. Also 

 when such mutants (auxotrophs) were supplied with the critical 

 substance whose biosynthesis was blocked, the microorganisms 

 were capable of completing the sequence to the aromatic acids. 



This route from carbohydrates to certain types of aromatic 

 substances has been established as quite general in metabolism. 



Biosynthesis of the chlorinated cyclopentane, caldariomycin. 



