SUBSTANCES PRODUCED BY ACTINOMYCETES 



197 



CnHasNAs + H.O- 



Streptomycin - 



NH + C.jH.jNO, 



CHNHC - NH2 

 CHOH 



-> Streptidine 



Streptobiosamine 



C,3H,3NO, + H,0 



H 

 HOC 



I 

 HOCH 



I 

 HOC - CHO 



I 

 HC 



H,C 



Streptobiosamine >■ Streptose 



CHOH 



I 

 CH3NHCH 



O HCOH 



I 

 HOCH 



I 

 CH 



I 

 CH,OH 



N-methyl/glucosamine 



Streptidine was characterized by the following crystalline salts: 

 dipicrate, sulfate, carbonate, dihydrochloride, dihydroiodide, dihelian- 

 thate, di-<:^-camphorsulfonate, and chloroplatinate. Streptidine appears 

 to contain one or more hydroxyl groups, but no primary amino, car- 

 boxy, methoxy, or carbonyl groups. It formed an octaacetyl derivative 



(713). 



Streptidine has the molecular formula C8H18N6O4. A further study 

 of this compound has been made by Carter et al. (114). Streptomycin 

 hydrochloride was completely inactivated on standing 24 hours in an- 

 hydrous i.O N methanolic hydrogen chloride without forming a new 

 basic group. The addition of two volumes of ether completely precipi- 

 tated the guanidine, which was previously reported by Carter et al. 

 (115) as one of the functional groups of streptomycin. From the 

 supernatant solution there is readily obtained an amorphous, optically 

 active hydrochloride of a nonguanidine base whose properties agree 



