Pfizer Handbook of Microbial Metabolites 1 08 



CH3(CH=CH) 



OH 



Auroglaucin 



It is likely that both polyenes and polyynes are acetate-de- 

 rived. It has been demonstrated^ that nemotinic acid with 11 

 carbon atoms is formed from 6 moles of an acetic acid deriva- 

 tive, with head to tail Hnkage and elimination of the terminal 

 methyl group. 



HC^C— C=C— CH=C=CH— CH— CHj— CH2— COOH 



OH 



Nemotinic Acid 



CH3— C=C— C=C— CH=C=CH— CH— CH2— CHo— COOH 



OH 

 Odyssic Acid 



Odyssic acid was presumed to be formed similarly, but with 

 terminal methyl group retention. 



In the examples available the acetylenic acids with an odd 

 number of carbon atoms terminate in an acetylenic bond. This 

 seems to indicate elimination of the terminal methyl group by 

 oxidation and decarboxylation. It is interesting to note that the 

 reverse process has been demonstrated in the conversion of 

 propynoic acid to acetylenedicarboxylic acid by a soil isolate.^ 



CO2 + HC^C— COOH -^ HOOC— C=C— COOH 



The xyloside of nemotinic acid also has been isolated.^ When 

 isolated from a culture grown on glucose with l-C"-labeled 

 acetic acid added to the medium, labeling is found in the poly- 

 acetylenes but not in the xylose moiety. When isolated from 



1 J. D. Bu'Lock and H. Gregory, Biochem. J. 72 322 (1959). 



2 Akira Hanaoka, Tokuya Harada and Takeo Takizawa, /. Agr. 

 Chem. Soc. Japan 26 151 (1952). 



3 J. D. Bu'Lock and H. Gregory, Experientia 15 420 (1959). 



