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Allyl esters and their application to the construction of solid phase systems for solid phase reactions

机译:烯丙基酯及其在固相反应固相体系构建中的应用

摘要

Allyl esters of the general formula I… X-CH2-CR1=CR2-CO-Y-R3-A (1 in which R1 and R2 are identical or different and are hydrogen, alkyl, aryl or halogen, R3 is a linker group (spacer), X is an acyloxy group, where acyl in the acyloxy group is the radical of an aliphatic carboxylic acid or is the radical RCO- in which R is an organic radical, Y has the meaning O, S or, in particular, NH and A is a group which is able to react with a solid support material F which contains suitable functional groups B, where A and B are atomic groups which react with one another by condensation and/or addition and formation of a link between the solid support material and the radical… X-CH2-CR1=CR2-CO-Y-R3-… can be used to construct solid phase systems which contain allylic side chains. The allyl esters I can be prepared in a straightforward manner in solution and then bonded to a solid support. The solid phase system prepared in this way is suitable for the solid phase synthesis of peptides and glycopeptides in which the peptides and glycopeptides can be selectively eliminated from the polymeric support under sufficiently mild conditions for there to be no cleavage of the glycosidic linkages or anomerisation.
机译:通式I的烯丙基酯…X-CH 2 -CR 1 = CR 2 -CO-YR 3 -A(1>其中R 1和R 2相同或不同并且为氢,烷基,芳基或卤素,R 3是连接基团(间隔基),X是酰氧基,其中酰氧基中的酰基是脂族羧酸的基团或是基团RCO-,其中R是在一个有机基团中,Y的含义为O,S或尤其是NH,并且A是能够与包含合适官能团B的固体载体材料F反应的基团,其中A和B是与通过在固体载体材料和基团之间的缩合和/或添加和形成键彼此相互连接... X-CH2-CR 1 = CR 2 -CO-YR 3 -...可用于构建固体含烯丙基侧链的固相体系,可以直接在溶液中制备烯丙基酯I,然后将其键合到固相载体上,以这种方式制备的固相体系适用于pe的固相合成肽和糖肽,其中可以在足够温和的条件下从聚合物载体上选择性地除去肽和糖肽,以使糖苷键不断裂或不异构化。

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