One Step Synthesis of Fmoc-Aminoacyl-N-alkylcysteine via the Ugi Four-Component Condensation Reaction
One Step Synthesis of Fmoc-Aminoacyl-N-alkylcysteine via the Ugi Four-Component Condensation Reaction
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Ugi四组分缩合反应一步合成Fmoc-氨基酰基-N-烷基半胱氨酸
DOI：
10.1021/acs.joc.9b02433
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发表时间：
2019
期刊：
影响因子：
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通讯作者：
Hojo Hironobu
中科院分区：
文献类型：
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作者：
Asahina Yuya;Hojo Hironobu
介绍了用Ugi四组分缩合反应快速制备fmoc -氨基酰基- n -烷基半胱氨酸二肽的方法。通过与市售的fmoc氨基酸、胺类、异氰化物和巯基乙醛衍生物的反应，一步合成了含有20种天然氨基酸残基的二肽，避免了s -三酰基半胱氨酸n -烷基化及其偶联反应的问题。将该二肽应用于fmoc固相合成多肽，并通过烷基半胱氨酸（NAC）辅助硫代酯化高效制备了多肽硫酯。
A prompt preparation method of the Fmoc-aminoacyl-N-alkylcysteine dipeptide by an Ugi four-component condensation reaction is described. Through a reaction with a commercially available Fmoc-amino acid, an amine, an isocyanide, and a mercaptoacetaldehyde derivative, one step synthesis of dipeptides containing 20 kinds of natural amino acid residues was achieved, which avoided the problematic N-alkylation ofS-tritylcysteine and its coupling reaction. The dipeptide was applied to the Fmoc-solid-phase peptide synthesis, and peptide thioesters were successfully obtained in high efficiency viaN-alkylcysteine (NAC)-assisted thioesterification.