(1) 



HO 



2NaI0 4 



HCOOH 



Kg" 



— co 2 



(S-4) 



COOH 



Cu, quinoline 



237 ( 



■*■ C0 2 

 (S-7) 



(3) COOH 



COOH 



COOH 



(S-l, 7) -*- 



+ 

 CHI 3 

 (S-2) 



COOH 



HO-Uu 





HO 



NaOI 



"^-^^OH 

 OH _ 



4 NaI0 4 



COOH 

 I 



C = 



CH 2 



CHO 



Formylpyruvic 

 acid 



4NaI0 4 



■*- 3 HCOOH 



-*- co 2 



(S-4, 5, 6) 



COOH 

 1 



2,4-DNPH C = N-NH-C 6 H 3 -(N0 2 ) 2 



" CH 2 



HC = N-NH-C 6 H 3 -(N0 2 ) 2 

 (S-7, 1,2,3) 



(4) 



HO" 



HOOC 



COOCH, 



COOH 



NaOH 



COOH 



(2,6) 



HOOC 



(3,5) 



(2,6) 



COOH 



(3,5) 



180° 



• C0 2 



(S-3,5) 



co 2 - 



(S-3,5) 



CH 2 NaIO< 

 (S-2, 6) -« 



+ 



COOH 

 1 



c = o 



I 

 CH 2 



£00; H 



COOH 

 I .OH 

 /< /OH 

 H 2 C CH 2 



I 

 COOH 



Os0 4 



COOH 



H 2 C 



CH 2 



COOH 



Itaconic 

 acid 



Fig. 1. Reactions used for the degradation of labeled shikimic acid. 



260 



