156 



J. BADDILEY 



TABLE I 

 Properties of Nucleosides 



Nucleoside M.p., °C. [«]„ (H2O) 



pK 



Derivatives 



Adenosine 229 



Guanosine 237-240 



Uridine 



165 



Cytidine 220-230 



Inosine 



Xanthosine 



Adenine deoxy- 

 riboside 



Hypoxanthine 

 deoxyriboside 



Guanine deoxy- 

 riboside 



Thymidine 



Cytosine deox- 

 yriboside 



Uracil deoxy- 

 riboside 



5-Methylcyto- 

 sine deoxy- 

 riboside 



218 



189-19096 



not sharp 



not sharp 



182-183 

 186 



1633 



-51.2° 

 (alkali) 



■21.0° 



-37.5° 



32.5° (in 



alkali) 



40.0° 



sugar 12.5 



hydrochloride, m.p. 

 161-164° (dec.)«6 



picrate, m.p. 175-178°, 

 is converted into thy- 

 midine by nitrous 

 acid^fia 



sides uridine and cytidine are obtained. ^^ Thymine nucleosides are synthe- 

 sized in a similar manner from 2,6-diethoxy-5-methylpyrimidine.^^ 



91 G. A. Howard, B. Lythgoe, and A. R. Todd, /. Chem. Soc. 1947, 1052. 



92 D. W. Visser, I. Goodmann, and K. Dittmer, /. Am. Chem. Soc. 70, 1926 (1948). 



93 P. A. Levene, /. Biol. Chem. 41, 483 (1920) ; cf . P. A. Levene, H. S. Simms, and L. 

 W. Bass, ibid. 70, 243 (1926). 



9" P. A. Levene and H. S. Simms, /. Biol. Chem. 65, 519 (1925). 



9* H. Steudel and R. Freise, Z. physiol. Chem. 120, 126 (1922). 



96 W. Andersen, C. A. Dekker, and A. R. Todd, J. Chem. Soc. 1952, 2721. 



96=' C. A. Dekker and D. T. Elmore, /. Chem. Soc. 1951, 2864. 



