中山大学学报（自然科学版）（中英文）2024，Vol.63Issue(2)：168-180,13.DOI:10.13471/j.cnki.acta.snus.2023C008
水液相下两性组氨酸分子对映异构的密度泛函理论
DFT study on the enantiotropy of amphoteric His molecule in water-liquid phase environment
摘要
Abstract
The title reaction was performed using the M06-2X and MN15 methods of DFT combined with the Slovation Model Density(SMD)model method based on self-consistent reaction field theory.The results showed that,His molecule can be transferred when the carbonyl O atom as the only bridge of α-H proton,and α-H transfers with amino group N and carbonyl O atom as bridges after the proton of protonated amino group N transfers to carbonyl O atom,respectively;Also,α-H achieves enantiotropy in five channels using amino group N and carbonyl group O as bridges after the proton transfers from the protonated amino group N to the N of the imidazole ring,respectively.Investigation on the potential energy surface showed that the free energy barriers of rate-determining step for each of the five channels are 245.6,238.1,297.3,270.9 and 257.7 kJ/mol under the effect of recessive solvent;the energy barriers are reduced to about 139.9,120.7,161.7,142.7 and 157.3 kJ/mol under the effect of dominant solvent.The results show that His can racemize with a small amount in the water-liquid environment,and it is relatively safe to be used to supply His for life.关键词
组氨酸/对映异构/密度泛函理论/过渡态/吉布斯自由能垒Key words
histidine/enantiotropy/density functional theory/transition state/Gibbs free energy分类
化学化工引用本文复制引用
牛鹤丽,徐岩,杨应,孙艳雨,郝成欣,姜春旭,王佐成,杨晓翠..水液相下两性组氨酸分子对映异构的密度泛函理论[J].中山大学学报（自然科学版）（中英文）,2024,63(2):168-180,13.基金项目
白城医学高等专科学校高层次人才团队建设项目(BCYZ20220302) （BCYZ20220302）
吉林省科技厅自然科学基金(20130101131JC) （20130101131JC）
