期刊
BIOCHEMISTRY
卷 44, 期 12, 页码 4949-4956出版社
AMER CHEMICAL SOC
DOI: 10.1021/bi047303g
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资金
- NIAID NIH HHS [AI0-54007-01] Funding Source: Medline
- NIGMS NIH HHS [GM20011] Funding Source: Medline
- PHS HHS [66174] Funding Source: Medline
Simocyclinone D-8 consists of an anguicycline C-glycoside tethered by a tetraene diester linker to an aminocoumarin. Unlike the antibiotics novobiocin, clorobiocin, and coumermycin A,, the phenolic hydroxyl group of the aminocoumarin in simocyclinone is not glycosylated with a decorated noviosyl moiety that is the pharmacophore for targeting bacterial DNA gyrase. We have expressed the Streptomyces antibioticus simocyclinone ligase SimL, purified it from Escherichia coli, and established its ATP-dependent amide bond forming activity with a variety of polyenoic acids including retinoic acid and fumagillin. We have then used the last three enzymes from the novobiocin pathway, NovM, NovP, and NovN, to convert a SimL product to a novel novobiocin analogue, in which the 3-prenyl-4-hydroxybenzoate of novobiocin is replaced with a tetraenoate moiety, to evaluate antibacterial activity.
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