3^7 



Amino Acids and Related Compounds 



The benzene ring of tryptophan also arises from the shikimic 

 acid route. The intermediates are unknown between shi- 

 kimic acid and the first aromatic member of the sequence, 

 anthranilic acid: 



NHo 



— COOH 



:OOH 

 Anthranilic Acid 



Shikimic Acid 



The remainder of the sequence in its present state of devel- 

 opment is as follows: 



COOH 5-Phosphoribosyl- 

 1 -pyrophosphate 



COOH 



NH2 

 Anthranilic Acid 



CH— CH— CH— CH— CH2— O— PO3H2 



NH OH OH 



N-(2-Carboxy phenyl)-! -aminoribose-5-phosphate 



Co 



^CH— CH— CH2 



I I I 

 OH OH O— PO2H2 



Triose- ^^ 

 phosphate 



lndolyl-3-glycerol 

 Phosphate 



L-Se 



Amadori rearrangement 

 COOH 



NH— CH2— CO— CH— CH— CH2— OPOaHs 



OH OH 



1 -Deoxy-1 -(o-carboxyanilino)-ribulose 



,CH.— CH— COOH 



I 

 NH2 



Indole Tryptophan 



There appears to be some question as to whether the Amadori 

 rearrangement product is a bona fide member of this sequence. 

 It has been isolated from Aerobacter aerogenes and character- 

 ized as derivatives, and it substitutes for anthranilic acid in bac- 

 terial mutants requiring the latter. 



The anthranilic acid carboxyl group is known to be lost as 

 carbon dioxide during the formation of the pyrrole ring, and 

 the first two carbon atoms of ribose are known to form the 2 

 and 3 positions of the indole ring. Glucose also can furnish 

 these two carbon atoms. In this connection it should be men- 



