CHEMISTRY OF PURINES AND PYRIMIDINES 



99 



(XXVIII) given here is arbitrary in that the configuration of the glucose 

 portion is not yet known. Three nucleotide derivatives, all of which in- 

 clude uridine-5'-pyrophosphate attached to an aminosugar by an acetal- 

 hke bond, accumulate in penicillin-treated cultures of S. Aureus i^"" '^^^ 

 one of these substances contains an L-alanine residue and another contains 

 a peptide composed of L-lysine, D-glutamic acid, and three alanine residues. 



CH.OH 



OH OH OH 



XXVIII 



Uridine diphospate glucose 



OH 



H2N N 



N 



OH 



OH 



XXIX 

 Vicine 



H,N N NH2 



XXX 



Divicine 



Vicine (CioH]607N4) was isolated from legumes of the species vicia in 

 1870 by Ritthausen2''2-204 g^^^^j appears to be the first simple pyrimidine 

 derivative found in nature. It also occurs^'^ in beet juice-"^ and peas.^"® 

 Upon mild acid hydrolysis, it yields the aglucone divicine (C4H602N4)2''^'^''^ 

 and D-glucose.2°^'2°^ Johnson'"* '^-"^'-'^ suggested a "pyrimidine-nucleoside" 

 structure for vicine. Levene found'^ ■-"•-'' that half of the nitrogen of vicine 



^oo J. T. Park, ref. 122, p. 93. 



201 J. T. Park, J. Biol. Chem. 194, 877, 885, 897 (1952). 



2»2 H. Ritthausen and V. Kreusler, /. prakt. Chcm. [2] 2, 333 (1870). 



203 H. Ritthausen, /. prakt. Chem. [2] 7, 374 (1873); 59, 480, 482 (1899). 



^0* H. Ritthausen, Ber. 9, 301 (1876); 29, 2108 (1896). 



205 E. O. von Lipmann, Ber. 29, 2653 (1896). 



^os E. Schultz, Z. physiol. Chem. 15, 140 (1890); 17, 215 (1893). 



20^ E. Fischer, Ber. 47, 2611 (1914). 



208 H. H^rissey and J. Cheymol, Bull. soc. chim. hiol. 13, 29 (1931). 



209 T. B. Johnson, /. Am. Chem. Soc. 36, 337 (1914). 



2'o T. B. Johnson and C. O. Johns, /. Am. Chem. Soc. 36, 545 (1914 . 



2'i P. A. Levene, /. Biol. Chem. 18, 305 (1914). 



2'2 P. A. Levene and J. K. Senior, /. Biol. Chern. 25, 607 (1916). 



