433 Thiophenes, Imidazoles, Thiazoles, Isoxazoles 



910 Penicillin F (Flavicidin, Flavicin) Ci4H.o04N.,S, m.p. (Na salt) 



204° (dec), [oc]v-"-' +276-316° (c 0.821 in water). 



R = n-Pentenyl CH3CH,— CH=CH— CH2— 



The A"-pentenyl variant is also known. 



Penicillium species, especially P. chrysogenum and 

 P. notatum Westling, and aspergillus species, especially 

 A. fiaviis from which Penicillin F was obtained. 



H. Clarke, J. Johnson and R. Robinson, "The Chemistry of 

 Penicilhn," Princeton University Press, Princeton, 1949. (A 

 review ) 



911 Cephalosporin C, proposed molecular formula CigHsiOgNgS, Na 



salt: [aW +103°. 



Structural features: 



Acid hydrolysis yields 1 D-a-aminoadipic acid, 1 CO2 

 and 2 NH3. No penicillamine is produced in contrast to 

 cephalosporin N. 



Cephalosporium salmosynnematum 



G. G. F. Newton and E. P. Abraham, Biochem. J. 62 651 

 (1956). 



912 Biocytin, C16H08O4N4S, colorless crystals, m.p. 228-230° (dec.) 



(245-252°). 



O 



/K 



HN NH 



I I 



CH CH 



I I 



CH2 CH— (CH2)4— CO— NH— (CH2)4— CH— COOH 



^ NH2 



Yeast 



Lemuel D. Wright, Emlen J. Cresson, Helen R. Skeggs, 

 Thomas R. Wood, Robert L. Peck, Donald E. Wolf and Karl 

 Folkers, /. Am. Chem. Soc. 72 1048 (1950). (Isolation) 



Robert L. Peck, Donald E. Wolf and Karl Folkers, ibid. 74 

 1999 (1952). (Structure) 



Donald E. Wolf, John Valiant, Robert L. Peck and Karl 

 Folkers, ibid. 74 1002 (1952). (Synthesis) 



