427 Thiophenes, Imidazoles, Thiazoles, Isoxazoles 



Junipal appears to be related to the acetylenic* sub- 

 stances typical of basidiomycetes which were listed in an 

 earlier section. In some way sulfur seems to have been 

 added, in effect across two acetylenic bonds to form a 

 thiophene ring. It has been suggested" that junipal and 

 anisaldehyde, occurring in the same culture and with the 

 same number of carbon atoms, may be derivatives of a 

 common acetylenic aldehyde precursor, perhaps C7H4O: 



CHO 

 HC = C— C = C— CH=CH— CHO 



CHO 



OCH 



Azomycin seems to incorporate a modified guanidine 

 group. 



893 Azomycin (2-Nitroimidazole), C3H3O2N3, white needles, m.p. 

 283° (dec). 



N NH 



I 



N02 



Nocardia sp. resembling N. mesenterica 

 Shoshlro Nakamura and Hamao Umezawa, /. Antibiotics 

 (Japan) 8A 66 (1955) and other papers in this series. 



894 Oxamycin (Cycloserine, Orientomycin D-4-Amino-3-isoxazoli- 

 done, PA-94), CsHgOoNo, colorless crystals, m.p. 156° 

 (dec), [a]546i 25° +137° ±2° (c 5 in 2 N sodium hydrox- 

 ide). 



CH2 CH— NH2 



I I 



o c=o 



H 



Streptomyces garyphalus, S. orchidaceus, S. lavendulae, 

 S. nagasakiensie nov. sp., S. K-300, etc. 



^-i J. H. Birkinshaw and P. Chaplen, Biochem. J. 60 255 (1955). 



