葡萄糖醛酸衍生物的合成及结构鉴定

Investigation about the synthesis and structure determination of glycopeptide containing glucuronic acid

目的研究用N,N-二环己基羰二亚胺和N-羟基苯并三唑催化葡萄糖醛酸与精氨酰-甘氨酰-天冬氨酰-苯丙氨酸反应合成四肽的方法。方法葡萄糖醛酸在四氢呋喃中与精氨酰-甘氨酰-天冬氨酰-苯丙氨酸反应,所得产物经柱层析分离纯化后,运用核磁共振氢谱、核磁共振碳谱、质谱对其结构进行鉴定。结果四-乙酰基葡萄糖醛酸50 mg通过反应制得目标化合物59 mg,产率为43%,结构确定为含葡萄糖醛酸的四肽产物。结论建立了葡萄糖醛酸和精氨酰-甘氨酰-天冬氨酰-苯丙氨酸合成四肽的方法,达到了预期目的。

Objective To research tetra- peptide synthesis glucuronic acid and arginine- glycine- asparagine- phenylalanine peptide sequence were reacted using the standard coupling method dicyclohexylcar—bodiimide and 1- hydroxybenzotriazole in solution.Methods Glucuronic acid was reacted with arginine- glycine- asparagine- phenylalanine peptide sequence in tetrahydrofuran to give tetra- peptide.The product obtained was purified by silica gel column chromatography and the structure of product was determined by nuclear magnetic resonance and mass spectroscopy.Results The product was afforded 59 mg in 43%yield using50 mg tetraacetyl glucuronic acid and the structure of tetra- peptide containing glycosylation was determined.Conclusion The reaction of glucuronic acid with peptide was explored and an effective procedure for the preparation peptide mimetic containing glucuronic acid was established.