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首页> 外文期刊>The Journal of Antibiotics: An International Journal >1,N'-(alpha-Aminoacyl)-and N'-alpha-(N~(alpha)-Alkylamino)acyl Derivatives of Vancomycin and Eremomycin I.Synthesis of N'-(alpha-aminoacyl)-and N'-alpha-(N~(alpha)-Alkylamino)acyl Derivatives of Vancomycin and Eremomycin by Selective Aminoacylation o
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1,N'-(alpha-Aminoacyl)-and N'-alpha-(N~(alpha)-Alkylamino)acyl Derivatives of Vancomycin and Eremomycin I.Synthesis of N'-(alpha-aminoacyl)-and N'-alpha-(N~(alpha)-Alkylamino)acyl Derivatives of Vancomycin and Eremomycin by Selective Aminoacylation o

机译：万古霉素和埃雷霉素的1，N'-（α-氨基酰基）-和N'-α-（N〜α-烷基氨基）酰基衍生物I.N'-（α-氨基酰基）-和N'-α的合成万古霉素和埃雷霉素的-（N〜（α）-烷基氨基）酰基衍生物的选择性氨基酰化反应

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摘要

The acylation of unprotected vancomycin or eremomycin with activated esters of N~(alpha)-protected amino acids or N~(alpha)-alkyl-N~(alpha)-Fmoc-amino acids is directed selectively to the amino group of the disaccharide branch (N') and after Fmoc-group removal leads to the corresponding N'-alpha-aminoacyl derivatives.A series of N'-alpha-aminoacyl and N'-alpha-(N~(alpha)-alkylamino)acyl derivatives of eremomycin and vancomycin containing hydrophobic moieties has been synthesized.The structures of all derivatives were confirmed by Electrospray Ionization mass-spectral (ESI MS) analysis,and by chemical degradation methods.Position of the introduced N'-a-aminoacyl-and N-(N~(alpha)-alkylamino)acyl groups were determined after Edman degradation and acidic hydrolysis.The structures of the synthesized starting reagents (N~(alpha)-alkylamino acids or N~(alpha)-alkyl-N~(alpha)-Fmocamino acids) were confirmed by NMR-spectra data.In general,N'-(N-alkylglycyl)-derivatives were more active than the corresponding N'-alpha-(N~(alpha)-alkylamino)acylated derivatives containing other amino acids (L-Lys,L-Met,L-Orn,L-and D-Ala,L-and D-Phe and benzyl-O-L-Tyr).
机译：未保护的万古霉素或埃雷霉素与N〜α-保护的氨基酸或N〜α-烷基-N〜α-Fmoc-氨基酸的活化酯的酰化作用选择性地指向二糖分支的氨基（N'）和Fmoc-基团去除后会产生相应的N'-α-氨基酰基衍生物和埃雷霉素的N'-α-氨基酰基和N'-α-（N〜（α-烷基氨基）酰基通过电子喷雾电离质谱（ESI MS）分析和化学降解方法确定了所有衍生物的结构。引入的N'-a-氨基酰基-和N-（N经Edman降解和酸水解后确定〜α-烷基氨基）酰基。合成的起始试剂（N〜α-烷基氨基酸或N〜α-烷基-N〜α-Fmocamino）的结构通常，N'-（N-烷基甘氨酰）衍生物的活性要比NMR高。相应的含有其他氨基酸（L-Lys，L-Met，L-Orn，L-和D-Ala，L-和D-Phe和苄基- OL-Tyr）。

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