Synthesis and intramolecular reactions of Tyr-Gly and Tyr-Gly-Gly related 6-O-glucopyranose esters
作者:Lidija Varga-Defterdarović、Gorana Hrlec
DOI:10.1016/j.carres.2003.07.011
日期:2004.1
6-O-(L-Tyrosylglycyl)- and 6-O-(L-tyrosylglycylglycyl)-D-glucopyranose were synthesized by condensation of the pentachlorophenyl esters of the respective di- and tripeptide with fully unprotected D-glucose. The intramolecular reactivity of the sugar conjugates was studied in pyridine-acetic acid and in dry methanol, at various temperatures and for various incubation times. The composition of the incubation
通过各自二肽和三肽的五氯苯基酯与完全未保护的D-葡萄糖的缩合合成6-O-(L-酪氨酰糖基)-和6-O-(L-酪氨酰糖基)-D-吡喃葡萄糖。在吡啶-乙酸和无水甲醇中,在各种温度和不同的孵育时间下研究了糖缀合物的分子内反应性。通过反相HPLC方法监测孵育混合物的组成,该方法允许同时分析起始材料的消失以及重排和降解产物的出现。为了确定肽羧基的酯化对其氨基反应性的影响,进行了平行实验,其中在相同的反应条件下,将游离肽与D-葡萄糖(摩尔比为1:1和1:5)。取决于起始化合物,获得了不同类型的Amadori产物(环状和双环形式),肽的甲基酯和Tyr-Gly-二酮哌嗪。