A Biomimetic Approach to Lanthionines

The asymmetric sulfa-Michael additions of appropriately protected l- and d-cysteine derivatives to new chiral dehydroamino acid derivatives have been developed as key steps in the synthesis of biologically important cysteine derivatives, such as lanthionine (Lan) and β-methyllanthionine (MeLan), which are unusual bis-α-amino acids found in the emerging lantibiotics such as nisin.

以适当保护的L-型与D-型半胱氨酸衍生物为底物，与新型手性脱氢氨基酸衍生物进行不对称硫杂迈克尔加成反应，该反应已被开发为合成具有重要生物活性的半胱氨酸衍生物的关键步骤。此类目标衍生物包括羊毛硫氨酸（Lan）与β-甲基羊毛硫氨酸（MeLan），二者均为在乳链菌肽等新兴羊毛硫抗生素中发现的罕见双α-氨基酸。