Studies on the reductive amination of 3-deoxy-D-manno-octulosonic acid (Kdo)
Studies on the reductive amination of 3-deoxy-D-manno-octulosonic acid (Kdo)
复制标题
3-脱氧-D-甘露辛糖酸(Kdo)的还原胺化研究
作者：
H. Grimmecke;H. Brade
3-脱氧-d -甘露辛酮酸（Kdo）与烯丙胺（AllN）或2-（4-氨基苯基）乙胺（APEA）还原胺化反应生成2- n -烯丙胺和2- n -[2-（4-氨基苯基）乙胺]-2,3-二脱氧-d -甘油-d -半乳糖-和2,3-二脱氧-d -甘油-d -talo-辛酮酸的外聚体对。由于Kdo还原成相应的多元醇作为副反应产物，产率为50-60%。质谱分析证实了胺化衍生物是预期的氨基。利用核磁共振（NMR）对2- n -烯丙基氨基-2,3-二脱氧辛酸进行了研究，该酸代表了由细菌脂多糖（LPS）经酸水解和还原烯丙基氨基化而得到的烯丙基层合寡糖的链端。
Reductive amination of 3-deoxy-D-manno-octulosonic acid (Kdo) with allylamine (AllN) or 2-(4-aminophenyl)ethylamine (APEA) yields epimer pairs of 2-N-allylamino and 2-N-[2-(4-aminophenyl)ethylamino]-2,3-dideoxy-D-glycero-D-galacto- and-2,3-dideoxy-D-glycero-D-talo-octonic acid. The yields were 50–60% due to reduction of Kdo to the respective polyols as side reaction products. Mass spectrometric analyses proved the amination derivatives to be the expected glycamines. Nuclear magnetic resonance (NMR) studies were performed on 2-N-allylamino-2,3-dideoxyoctonic acid which represents the chain terminus of allylaminated oligosaccharides derived from bacterial lipopolysaccharides (LPS) after acid hydrolysis and reductive allylamination.