166 



J. BADDILEY 



PO3H2 



-]-o- 



P0,H2 



OH 



i I 

 ■CH-CH'CH-CH-CH,-OH 



XXVI 



Adenosine-2'-phosphate 



-0- 



OH O 

 I I 

 "-CH-CH-CH-CH-CHs-OH 



T N 



NH2 



XXVII 



Adenosine-3'-phosphate 



was believed to be identical with that from guanylic acid and gave on oxida- 

 tion a ribonic acid phosphate which differed in rate of lactonization and 

 hydrolysis from ribonic acid-S-phosphate.^®^ Furthermore, it was reduced 

 catalytically to an optically inactive ribitol phosphate. ^^^ If the yeast 

 adenylic acid in the first place was a single substance, and if no migration 

 of phosphate groups had occurred during subsequent hydrolysis and re- 

 duction, then the above transformations would indicate that the nucleotide 

 is adenosine-3'-phosphate yielding ribose-3-phosphate, and ribitol-3-phos- 

 phate. 



PO3H, 



-0- 



OH O OH 

 I I I 

 HO-CH-CH-CH-CH-CHs 



Ribose-3-phosphate 



P0,H2 

 OH 



OH 



Ribonic acid-3-phosphate 



OH O 



I I I 

 H02C-CH-CH-CH-CH 



POjHj 



OH O OH 



I I I 



H0-CH2- CH-CH-CH-CH^-OH 



Ribitol-3-phosphate 



Since it is now known that both a and h forms of adenylic acid are produced 

 by hydrolysis of ribonucleic acid^^^ and also since it has been shown that 

 these acids are rapidly interconvertible under mild acid conditions, ^^"^ "' 

 the structural investigations on yeast adenylic acid are of little value. 



Adenylic acids a and h are both dephosphorylated enzymically to adeno- 

 sine, ^^^^ ^^^ are stable to periodate oxidation, '^^ and are relatively stable to 

 alkali. These properties agree with those expected for adenosine-2'- and 



1" P. A. Levene and S. A. Harris, J. Biol. Chem. 95, 755 (1932). 



i«» P. A. Levene and S. A. Harris, J. Biol. Chem. 98, 9 (1932). 



»«» C. E, Carter and W. E. Cohn, Federation Proc. 8, 190 (1949). 



"» D. M. Brown and A. R. Todd. J. Chem. Soc. 1952, 44. 



"1 D. M. Brown, L. J. Haynes, and A. R. Todd, /. Chem. Soc. 1950, 2299. 



