3-amino-5-hydroxybenzoic acid in antibiotic biosynthesis. XI. Biological origins and semisynthesis of thionaphthomycins, and the structures of naphthomycins I and j

被引:13
作者
Hooper, AM [1 ]
Rickards, RW [1 ]
机构
[1] Australian Natl Univ, Res Sch Chem, Canberra, ACT 0200, Australia
关键词
D O I
10.7164/antibiotics.51.845
中图分类号
Q81 [生物工程学(生物技术)]; Q93 [微生物学];
学科分类号
071005 ; 0836 ; 090102 ; 100705 ;
摘要
Fermentations of Streptomyces sp. E/784 produce low levels of the novel C-30 alkylthio-substituted ansamycin antibiotics naphthomycins J (9) and I(10), in addition to the more abundant C-30 hydroxylated analogues actamycin (1) and naphthomycin D (2) and C-30 chlorinated analogues naphthomycins H (3) and A (4). The addition of N-acetyl-L-cysteine to the fermentation medium substantially increases the production of the thionaphthomycins J and I at the expense of their chloro analogues H and A. Other thiols and thiol progenitors are similarly utilised, including N-acetyl-L-cysteine methyl ester which affords the known naphthomycin F (8) and its novel 2-demethyl homologue (7). The formation of thioansamycins from chloroansamycins and thiols in vivo is probably non-enzymic since similar conversions can be effected in vitro.
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页码:845 / 851
页数:7
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