CHEMISTRY OF PURINES AND PYRIMIDINES 95 



covered by Cantoni. The antibacterial agent, cordycepin, isolated'*^ from 

 cultures of the mold Cordyceps militaris (Linn.) Link, is^^^ an adenine-9- 

 nucleoside of cordycepose, a branched 3-deoxypentose related structurally 

 to apiose. Adenine is present in pseudovitamin Bio , thus replacing 5,6- 

 dimethylimidazole in the nucleotide portion of B12 }'^' An antibiotic, Puro- 

 mycin, occurring in the mold Strepto7nyces alboniger, has been found to be 

 active against certain bacteria and Trypanosomes;'^* upon acid hydrolysis 

 it yields the dimethyladenine, 6-dimethylaminopurine, and D-3-amino- 

 ribose and O-methyl-L-tyrosine.^^^ In its proposed structure, Puromycin is 

 shown'*^ as a 9-[0-methyl-L-tyrosyl-A^-3'-aminoribosyl]-6-dimethylamino- 

 purine. G-Dimethylaminopurine has previously been synthesized by the 

 reaction of 6-methylmercaptopurine with dimethylamine.'^" 



In addition to its presence in the free form in bird droppings and other sources al- 

 ready mentioned, guanine has an interesting distribution in nature. It accounts for the 

 iridescence of fish scales'^'"'" and as such in many teleosts is an inexpensive source of 

 "pearl essence."'"' ''*■' It was used in 1656 in France to impart a pearly appearance to 

 beads. "^ Guanine is found in the eyes of the dogfish''*® (cf. Hopkins'^'), in the excreta 

 of spiders, '''* in sugar and refuse molasses,'''^ and (with xanthine) in the shoots of a 

 food-herb (Aralia cordata) commonly used in Japan. '5° The white, shiny appearance 

 of the skin of many amphibia and reptiles is due to the presence of guanine (see Abder- 

 halden, "Biochemisches Handlexikon," in the General References section). 



Guanine accumulates'*' in large crystalline masses in the bones and other tissues of 

 the pig in a metabolic disorder'^^ that bears a strong resemblance to human gout. The 



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1951, 2299. 

 i3« H. R. Bentley, K. G. Cunningham, and F. S. Spring, J. Chern. Soc. 1951, 2301. 

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N. Bohonos, and J. H. Williams, Antibiotics & Chemotherapy 2, 409 (1952). 

 "8 C. W. Waller, P. W. Fryth, B. L. Hutchings, and J. H. Williams, /. Am. Chem. Soc. 



75, 2025 (1953). 

 "" G. B. Elion, E. Burgi, and G. H. Hitchings, J. Am. Chem. Soc. 74, 411 (1952). 

 1" Barreswill, Ann. 122, 128 (1862). 

 >« A. Bethe, Z. physiol. Chem. 20, 472 (1895). 



'" G. H. Hitchings and E. A. Falco, Proc. Natl. Acad. Sci. U. S. 30, 294 (1944). 

 '■•^ D. K. Tressler and J. MacW. Lemon, "Marine Products of Commerce," 2nd ed., 



p. 117. Reinhold, New York, 1951. 

 '■•^ H. F. Taylor, in "Marine Products of Commerce" (D. K. Tressler, ed.), p. 161. 



Chemical Catalog Co. New York, 1923. 

 "« A. Pirie and D. M. Simpson, Biochem. J. 40, 14 (1946). 

 1" F. G. Hopkins, Proc. Roy. Soc. (London) B130, 359 (1941-42). 

 "8 E. Gorup-Besanez and F. Will, Ann. 67, 117 (1849). 

 i^« E. C. Shorey, /. Am. Chem. Soc. 21, 609 (1899). 

 ISO K. Miyake, /. Biol. Chem. 21, 507 (1915). 



"1 R. Virchow, Arch, pathol. Anat. u. Physiol. (Virchow's) 35, 358 (1866) ; 36 , 147 (1866). 

 1" W. Mendelson, Am. J. Med. Sci. 95, 109 (1888). 



