新产品编号:870609
Chemical Name: N-Decanoyl-L-tryptophyl-L-asparaginyl-L-aspartyl-L-threonyl-glycyl-Ndelta-(DL-tryptophyl)-L-ornithyl-L-aspartyl-D-alanyl-L-aspartyl-glycyl-D-seryl-threo-3-methyl-L-glutamyl-gamma-(2-aminophenyl)-gamma-oxo-L-alpha-aminobutyric acid C-1.13-O-2.4-lactone; 6-(N5-DL-Tryptophyl-L-ornithine)daptomycin
CAS No. 345643-58-5 (L-isomer)
项目整合开发状态: Preclinical
项目研究机构: Cubist (Originator)
合成路线:Daptomycin (I) was obtained as a fermentation product from Streptomyces roseosporus.Selective acylation of (I) at the lysine side-chain amino group by means of N-Boc-tryptophan activated as either the pentafluorophenyl (II) or the p-nitrophenyl ester (III) furnished the corresponding tryptophan amide (IV).
合成路线:The N-Boc group of (IV) was then removed by treatment with trifluoroacetic acid in the presence of thioanisole or in the presence of ethanedithiol and triethylsilane to furnish the desired lipodepsipeptide.
合成路线:The title compound is prepared by reductive alkylation of daptomycin (I) with 2 imidazolecarboxaldehyde (II) in the presence of NaBH(OAc)3 in DMF.
📌 参考资料/链接：
参考文献标题:Lipopeptides as antibacterial agents
文献作者:Watson,A.D.; Hill,J.; Zhang,Y.; Finn,J.; Yu,X.Y.; Keith,D.; Morytko,M.; Parr,I.; Siedlecki,J.; Silverman,J.; Christensen,D.; Lazarova,T.(Cubist Pharmaceuticals,Inc.)
参考来源:WO 0144274
📄 详细内容
合成路线:Daptomycin (I) was obtained as a fermentation product from Streptomyces roseosporus.Selective acylation of (I) at the lysine side-chain amino group by means of N-Boc-tryptophan activated as either the pentafluorophenyl (II) or the p-nitrophenyl ester (III) furnished the corresponding tryptophan amide (IV).
合成路线:The N-Boc group of (IV) was then removed by treatment with trifluoroacetic acid in the presence of thioanisole or in the presence of ethanedithiol and triethylsilane to furnish the desired lipodepsipeptide.
参考文献标题:Novel lipopeptides 1: Synthesis and biological activity of ornithine amino amide analogs of daptomycin
文献作者:Silverman,J.; Finn,J.; Keith,T.L.D.; Hill,J.M.; Parr,I.; Morytko,M.; Oliver,N.; Laganas,V.; Yu,X.
参考来源:41st Intersci Conf Antimicrob Agents Chemother (Dec 16 2001,Chicago) 2001,Abst F-1150
合成路线:Daptomycin (I) was obtained as a fermentation product from Streptomyces roseosporus.Selective acylation of (I) at the lysine side-chain amino group by means of N-Boc-tryptophan activated as either the pentafluorophenyl (II) or the p-nitrophenyl ester (III) furnished the corresponding tryptophan amide (IV).
参考文献标题:Synthesis and biological activity of N-Acylated ornithine analogues of daptomycin
文献作者:Hill,J.; Siedlecki,J.; Parr,I.; Morytko,M.; Yu,X.; Zhang,Y.; Silverman,J.; Controneo,N.; Laganas,V.; Li,T.; Lai,J.-J.; Keith,D.; Shimer,G.; Finn,J.
参考来源:Bioorg Med Chem Lett 2003,13(23),4187