Institute of Chemistry, Center for Glycomics, GLYCOMED, Slovak Academy of Sciences, SK-84538 Bratislava, Slovakia.
Carbohydr Res. 2011 May 1;346(6):715-21. doi: 10.1016/j.carres.2011.02.007. Epub 2011 Mar 1.
Sodium methoxide-promoted methanolysis of 7-deoxy-7-nitro-L-glycero-L-galacto-heptitol peracetate rapidly and nearly quantitatively accumulates 7-deoxy-6-O-methyl-7-nitro-L-glycero-L-galacto-heptitol. The prolonged treatment then provides 76% of D-galactofuranosyl nitromethanes and finally results in the equilibrium of 77% of β-D-galactopyranosyl nitromethane and 7-9% of three other tautomeric D-galactosyl nitromethanes. Thermal treatment of 7-deoxy-7-nitro-L-glycero-L-galacto-heptitol in boiling water peaks at a 58% content of D-galactofuranosyl nitromethanes and ends in a similar equilibrium mixture of four D-galactosyl tautomers. The relevant kinetic parameters of the latter transformation are determined by a curve fitting using the nonlinear least-squares Marquardt-Levenberg algorithm.
甲醇钠促进的 7-去氧-7-硝基-L-甘油-L-半乳糖庚糖五乙酸酯的甲醇解反应迅速且近乎定量地积累了 7-去氧-6-O-甲基-7-硝基-L-甘油-L-半乳糖庚醇。然后，长时间处理提供了 76%的 D-半乳糖呋喃糖基硝甲烷，最终达到了β-D-半乳糖吡喃糖基硝甲烷的平衡含量为 77%，以及 7-9%的三种其他互变异构的 D-半乳糖硝甲烷。在沸水浴中加热 7-去氧-7-硝基-L-甘油-L-半乳糖庚醇，其 D-半乳糖呋喃糖基硝甲烷的含量峰值为 58%，最终得到了四种 D-半乳糖互变异构体的类似平衡混合物。后一种转化的相关动力学参数通过使用非线性最小二乘 Marquardt-Levenberg 算法进行曲线拟合来确定。
