Shanghai Key Laboratory of Green Chemistry and Chemical Process, School of Chemistry and Molecular Engineering, East China Normal University, 3663 North Zhongshan Road, Shanghai 200062, P. R. China.
State Key Laboratory of Element-organic Chemistry, Nankai University, Tianjin 300071, P. R. China.
Org Lett. 2021 Nov 19;23(22):8862-8866. doi: 10.1021/acs.orglett.1c03370. Epub 2021 Nov 11.
A sulfur-involved ligation for thioamide quasi-peptides was developed via amino acids and amino aldehydes coupling. The key to the transformation was the chelation of copper with imines for chiral activation and fixation. In this environment, linear polysulfur decreased the alkalinity of single sulfur anions to prevent racemization caused by the interaction between sulfur and sodium sulfide. Dipeptides, tripeptides, tetrapeptides, and the linkage between the drug and amino acids were successfully obtained.
一种涉及硫的硫代酰胺拟肽的连接方法是通过氨基酸和氨基酸醛缩合开发的。该转化的关键是亚胺与铜的螯合，以实现手性的激活和固定。在这种环境下，线性多硫降低了单硫阴离子的碱性，以防止由于硫与硫化钠之间的相互作用而导致的外消旋化。成功获得了二肽、三肽、四肽以及药物和氨基酸之间的连接物。
