1-L-色氨酸-1-脱氧-D-果糖的合成及其热裂解

摘要

The aim of this article is to discuss feasibility of synthesis of 1-L-tryptophan-1-deoxy-D-fructose with D-mannose and L-tryptophan as raw materials. The synthesis condition was optimized through single factor experiment and orthogonal experiment. The objective product's structure was characterized by IR, NMR and HR-MS, and the pyrolysis behavior was investigated via pyrolysis-GC/MS. Results showed that the optimal synthetic conditions were confi rmed as follows: when the dosage of L-tryptophan was 30 mmol, reaction temperature was 65℃, reaction time was 6.0 h, reaction molar ratio of D-mannose and L-tryptophan was 1:1, catalyst dosage was 0.5mmol and solvent dosage was 80mL. Under optimal conditions, the yield reached 45.2%. The quantity of pyrolysis product increased with the rise of temperature,and pyrolysis produced more products in aerobic conditions than in anaerobic conditions.The pyrolysis product under the temperature of 600℃ and aerobic conditions possessed floral aroma, roasted aroma, nut aroma and caramel aroma. It's indicated that the synthesis route was feasible and eff ective.%为探索以D-甘露糖与氨基酸的美拉德反应制备Amadori化合物的可行性问题,以D-甘露糖和L-色氨酸为原料合成了1-L-色氨酸-1-脱氧-D-果糖,利用IR、NMR和HR-MS对产物进行了结构表征,采用单因素试验和正交试验优化了合成工艺,利用在线裂解气相色谱/质谱联用(Py-GC/MS)法研究了产物的热裂解行为.结果表明:①最佳合成条件为:当L-色氨酸投料量为30 mmol时,反应温度65℃、反应时间6.0 h、物料比1:1(D-甘露糖与L-色氨酸的物质的量比)、催化剂用量0.5 mmol及溶剂用量80 Ml,此条件下产率达到45.2%;②无论有氧或无氧条件下裂解,产物种类均随温度升高而增加,有氧条件裂解产物种类多于无氧条件;在600℃有氧条件下,1-L-色氨酸-1-脱氧-D-果糖裂解生成具有花香、烘烤香、坚果香、焦糖香等香韵的产物;③以D-甘露糖和L-色氨酸为原料合成1-L-色氨酸-1-脱氧-D-果糖的技术方法可行,产品收率较高.