Kononov L O, Kochetkov N K
N. D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the U.S.S.R., Moscow.
Carbohydr Res. 1991 Sep 2;216:381-98. doi: 10.1016/0008-6215(92)84175-r.
The disaccharides alpha-L-Rhap-(1----3)-beta-D-GlcpA and beta-D-GlcpA-(1----3)-alpha-L-Rhap bearing amide-linked L-serine or L-threonine, which represent the repeating unit(s) of the capsular polysaccharide from E. coli O6:K54:H10, have been synthesised. O-tert-Butyl-protected amino acid tert-butyl esters were condensed with the corresponding biouronic acid as the 2-acrylamidoethyl or 2-azidoethyl glycosides. The azido function was replaced by the acrylamido group by catalytic hydrogenation followed by N-acryloylation. The tert-butyl groups were removed by treatment with trifluoroacetic acid to give the target monomers which were copolymerised with acrylamide to give neoglycoconjugates that are potentially useful for immunochemical studies.
已合成了带有酰胺连接的L-丝氨酸或L-苏氨酸的二糖α-L-鼠李糖基-(1→3)-β-D-葡萄糖醛酸和β-D-葡萄糖醛酸基-(1→3)-α-L-鼠李糖，它们代表大肠杆菌O6:K54:H10荚膜多糖的重复单元。叔丁基保护的氨基酸叔丁酯与相应的双糖醛酸以2-丙烯酰胺基乙基或2-叠氮基乙基糖苷的形式缩合。通过催化氢化然后进行N-丙烯酰化，将叠氮基官能团替换为丙烯酰胺基。用三氟乙酸处理除去叔丁基，得到目标单体，其与丙烯酰胺共聚得到新糖缀合物，这些新糖缀合物可能对免疫化学研究有用。
