550 



THE BIOCHEMISTRY OF B VITAMINS 



biological action of oxybiotin is a property of the molecule. Since it is 

 not converted by the organisms into biotin, it must be utilized per se in 

 the formation of the necessary coenzyme (s), which in turn can function 



Table 13. Growth-promoting Activities of Analogues of Biotin and Oxybiotin. 



Compound 



(+)-Desthiobiotin°' 8 



DL-Desthiobiotin" •' 



DL-Desthioallobiotin 

 Biotin methyl ester' 



DL-Oxybiotin methyl ester' 

 Biotin sulfoxide methyl ester 8 



Biotin sulfone* 



«s-3,4-Diamino-2-tetra- 

 hydrothiophenevaleric acid' 



Organism 



Saccharomyces cerevisiae 



Lactobacillus casei 



Saccharomyces cerevisiae 



Rats* 



Saccharomyces cerevisiae 



Saccharomyces cerevisiae 



Lactobacillus casei 



Saccharomyces cerevisiae 



Saccharomyces cerevisiae 



Lactobacillus casei 



Saccharomyces cerevisiae 



Rats c 



Lactobacillus casei 



Saccharomyces cerevisiae 



Saccharomyces cerevisiae F.B. 



Lactobacillus casei 



Rats 



Lactobacillus arabinosus 



Lactobacillus casei 



Rats 



Lactobacillus arabinosus 



Lactobacillus casei 



Lactobacillus arabinosus 

 Lactobacillus casei 



Saccharomyces cerevisiae 

 Lactobacillus arabinosus 

 Lactobacillus casei 

 Saccharomyces cerevisiae 

 Lactobacillus casei 

 Saccharomyces cerevisiae 

 Lactobacillus casei 



DL-ct's-3,4-Diamino-2- 



tetrahydrothiophenevaleric 



acid' 

 DL-as-3,4-Diamino-2- 



tetrahydrofuranvaleric 



acid' 

 DL-Hexahy dro-2-oxo-l H- 



furo[3,4]imidazole-4- 



pentanol' 

 DL-Hexahydro-2-oxo-4- 



methyl-lH-furo[3,4]imid- 



azole 

 ( + )-f ,77-Diaminopelargonic 



acid* 

 DL-5-Methyl-2-thiono-4- 



imidazolidinecaproic acid 



■Active for Saccharomyces cerevisiae (25 strains), Saccharomyces chodati, Saccharomyces macedoniensis, 

 Endomycopsisfibuliger,Debaryomyces matruchoti v subglobosus, Mycoderma valida, Mycotorula lactis, Schizo- 

 saccharomyces pombe, Torula lactosa, Zygosaccharomyces lactis, Zygosaccharomyces marxianus, Neuro- 

 spora crassa, Neurospora sitophila, Ceratostomella ips 438, Ceratostomella montium, Leuconostoc mesenteroides, 

 Penicillium notatum 21464, Escherichia coli 58, Ceratostomella reukanfi, Schwanniomyces occidentalis 116. 14,51 

 54. 55 Inactive for Ceratostomella pini 416, Sordaria fimicola, Lactobacillus arabinosus, amd Rhizobium trifolii 

 205," Penicillium chrysogenum 62078."- " 



• Compound competitively inhibits utilization of biotin for this organism. 



• Biotin deficiency induced with raw egg white. 



d Only 35-50 per cent of optimal growth obtained with biotin is attained; inactive in the absence of 

 aspartic acid. 



• Configuration analogous to (+) biotin. 

 / Configuration analogous to Di^-biotin. 



rather efficiently in place of the natural coenzyme. It appears that the 

 sulfur atom of biotin is not essential for its biological action. 



Desthiobiotin. In the course of structural studies, 10 natural biotin was 

 treated with Raney's nickel to remove the sulfur atom of the tetrahydro- 



