Glucosamine condensation catalyzed by 1-ethyl-3-methylimidazolium acetate: mechanistic insight from NMR spectroscopy.
The basic ionic liquid 1-ethyl-3-methylimidazolium acetate ([C2C1Im][OAc]) could efficiently catalyze the conversion of 2-amino-2-deoxy-d-glucose (GlcNH2) into deoxyfructosazine (DOF) and fructosazine (FZ). Mechanistic investigation by NMR studies disclosed that [C2C1Im][OAc], exhibiting strong hydrogen bonding basicity, could coordinate with the hydroxyl and amino groups of GlcNH2via the promotion of hydrogen bonding in bifunctional activation of substrates and further catalyzing product formation, based on which a plausible reaction pathway involved in this homogeneous base-catalyzed reaction was proposed. Hydrogen bonding as an activation force, therefore, is responsible for the remarkable selectivity and rate enhancement observed.
The Biorefinery Research and Engineering Center, Institute of Coal Chemistry, Chinese Academy of Sciences, Taiyuan, People's Republic of China. houxl@sxicc.ac.cn wangyx@sxicc.ac.cn.
Lingyu
L
Jia
Christian Marcus
CM
Pedersen
Yan
Y
Qiao
Tiansheng
T
Deng
Pingping
P
Zuo
Wenzhi
W
Ge
Zhangfeng
Z
Qin
Xianglin
X
Hou
Yingxiong
Y
Wang
D002384:Catalysis; D005944:Glucosamine / Q000138:chemical synthesis* / Q000737:chemistry; D007093:Imidazoles / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
D007093:Imidazoles; D005944:Glucosamine; C518739:1-ethyl-3-methylimidazolium