3^9 Polypep t ides a nd Related Compounds 



Taiichi Ito, Sadao Miyamura, Seihachiro Niwayama, Masa- 

 nobu Oishi, Nobuhiro Igarashi, Hiromichi Hoshino and Shozo 

 Muto, ibid. 7B 147 (1954). 



Yasuo Kayama, Japanese Patent 1546 (1952). 



Takeshi Oda, Mitsuhiro Kinoshita, Osamu Yamanaka and 

 Fumio Ueda, /. Pharm. Soc. Japan 74 1234 (1954). 



Takeshi Oda and Fumio Ueda, ibid. 74 1246 (1954). 



772 Mycobactin, C^-H^.^Oi^N-, microcrystalline white powder with 

 pale green fluorescence, m.p. 165-166.5°, [a],,'' -19° (c 

 4.9 in chloroform). 



Mycobactin is a weak acid believed to have one of the 

 following structures: 



O— CH2 



/ 



ru C COOR OH 



^"^ \ II 



N— CH— CO— NH— CH— (CH2)4— N— CO— CH=CH(CH2)uCH3 



trans 



or 



CH3 



C OH COOR 



\ 



N— CH— CO— N— (CH.)4— CH— NH— CO— CH=CH(CH2),4CH3 



trans 



CH2— CH,— CH2 



I / 



R = CH3CH2CHCHCONH— CH 



I \ 

 CH3 CO N CH2 



OH 



Mycobacterium phlei 



The yield was about 67 g. from 41 kg. of moist cells. 

 G. A. Snow, J. Chem. Soc, 4080 (1954) and earlier papers 

 in the series. 



73 Geomycin (C,jHio02N2)8-i,„ HeHanthate red platelets, m.p. 205- 

 215° (dec). Hydrochloride [a],,-" +16°. 



A basic polypeptide. Acid hydrolysis yields: geamine, 

 /3-lysine, and an amino sugar, plus small amounts of 



