BIOTIN 



oxybiotin with S. cerevisiae, L. arabinosus and Streptococcus haemo- 

 lyticus ; most of the compounds were extremely potent with oxybiotin 

 as growth factor, but almost inactive with biotin.^^ Homo-oxybiotin 

 (w = 5) had no protective effect on mice infected with S. hcBmolyticus. 

 The sulphonic acid analogues of oxybiotin and homo-oxybiotin : 



CO 



NH NH 



I I 



CH— CH 



I I 



CH2 CH. (CH^j^.SOjH 



\/ 

 O 



were synthesised by Hofmann et al.^^> ^* The ^/-oxybiotin sulphonic 

 acid and the corresponding thiol and benzylthioether had pronounced 

 antibiotin and anti-oxybiotin activity for a number of micro-organisms. 

 The <^/-homo-oxybiotin sulphonic acid, however, had slight growth- 

 promoting activity, although the corresponding thiol and benzyl- 

 thioether were inhibitory to S. cerevisiae. 



4-Methyl-5-(e-sulphoamyl)-2-imidazolidone, the sulphonic acid 

 analogue of desthiobiotin also inhibited the growth of S. cerevisiae, 

 especially when oxybiotin or desthiobiotin was the growth factor ; 

 the compound had no effect on L. helveticus.^^ 



References to Section 19 



1. J. H. Mueller, K. S. Klise, E. F. Porter and A. Graybiel, /. Bad., 



1933. 25, 509 ; J. H. Mueller, ibid., 1935. 29, 515 > I935. 30, 513 ; 

 J. H. Mueller and I. Kapnick, ibid., 525 ; J. H. Mueller, ibid., 

 1936, 32, 207 ; J. H. Mueller and Y. SubbaRow, ibid., 1937, 34, 



153- 



2. J. H. Mueller, Science, 1937, 85, 502 ; /. Biol. Chem., 1937, 119» 



124 ; /. Bact., 1937, 34, 163. 



3. W. C. Evans. F. C. Happold and W. R. C. Handley, Brit. J. Exp. 



Path., 1939, 20, 41. 



4. V. du Vigneaud, K. Dittmer, E. Hague and B. Long, Science, 



1942, 96, 186. 



5. W. J. Robbins and R. Ma, ibid., 406. 



6. J. L. Stokes and M. Gunness, /, Biol. Chem., 1945, 157, 121. 



7. G. A. Emerson, ibid., 127. 



8. W. H. Ott. ihid., 131. 



8a. M. R. Belcher and H. C. Lichstein, /. Bad., 1949, 58, 565. 



9. L. C. Cheney and J. R. Piening, /. Anier, Chem. Soc, i945. 67, 



729, 731, 2213. 

 10. S. R. Safir, S. Bernstein, B. R. Baker, W. L. McEwen and Y. 

 SubbaRow, /. Org. Chem., 1947, 12, 475. 



454 



