通过脯氨酸催化甘氨酸席夫碱的羟醛缩合反应合成α,β-脱氢氨基酸
α,β-Dehydroamino Acid Synthesis through Proline-Catalyzed Aldol Condensation with a Glycine Schiff Base.
作者信息
Sawamura Jun, Ieiri Daikan, Yazaki Ryo, Ohshima Takashi
机构信息
Graduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka 812-8582, Japan.
出版信息
Precis Chem. 2023 Jun 8;2(1):14-20. doi: 10.1021/prechem.3c00048. eCollection 2024 Jan 22.
A general protocol for the synthesis of α,β-dehydroamino acids and their peptides was developed. Proline efficiently catalyzed an aldol condensation reaction of a glycine Schiff base with a variety of aldehydes. The hydroxy group on the benzophenone imine was crucial for high / selectivity and further transimination for protecting group-free α,β-dehydroamino esters. Peptide elongation of both the C- and N-terminals highlighted the usefulness of our present protocol.
开发了一种合成α,β-脱氢氨基酸及其肽的通用方案。脯氨酸有效地催化了甘氨酸席夫碱与多种醛的羟醛缩合反应。二苯甲酮亚胺上的羟基对于高选择性以及进一步的转亚胺化以制备无保护基的α,β-脱氢氨基酸酯至关重要。C端和N端的肽延伸突出了我们当前方案的实用性。
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