Insights into Fast Amide Couplings in Aqueous Nanomicelles

被引:24
作者
Sharma, Sudripet [1 ]
Kaur, Gaganpreet [1 ]
Handa, Sachin [1 ]
机构
[1] Univ Louisville, Dept Chem, Louisville, KY 40292 USA
基金
美国国家科学基金会;
关键词
amide couplings; micellar catalysis; chemistry in water; sustainability; PEPTIDE THERAPEUTICS; BOND FORMATION; REAGENTS; GREEN; SUSTAINABILITY; PERSPECTIVE; SOLVENT; WATER;
D O I
10.1021/acs.oprd.1c00203
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
1-Ethyl-3-(3-(dimethylamino)propyl)-carbodiimide (EDC center dot HCl) has both lipophilic and hydrophilic regions, causing self-aggregation (also called nanoparticle formation) in an aqueous medium containing PS-750-M amphiphile. Kinetic and proton nuclear magnetic resonance studies were used to probe the effect of different organic bases on the potential nanoparticle formation of EDC center dot HCl. It also reveals why the pyridine base works better under micellar conditions. The methodology was examined on the multigram scale synthesis of bioactive molecules, where excellent reaction yields were obtained without product epimerization while maintaining a shorter reaction time.
引用
收藏
页码:1960 / 1965
页数:6
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