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Synthesis of N-Glyoxylyl Peptides Enabled by a Lossen Rearrangement-Induced Intramolecular Redox Reaction of N-Terminal Glycyl Hydroxamic Acid
Organic Letters ( IF 5.2 ) Pub Date : 2024-05-13 , DOI: 10.1021/acs.orglett.4c01126
Junya Hayashi 1 , Daishiro Kobayashi 1 , Chizuru Namikawa 2 , Masaya Denda 1 , Akira Otaka 1
Affiliation  

An oxidant-free approach to the synthesis of N-glyoxylyl peptides has been developed that utilizes the Lossen rearrangement of the N-terminal glycyl hydroxamic acid residue. The synthesis proceeds via an intramolecular redox mechanism to yield the glyoxylyl peptides, which are then subjected to various peptide cyclization procedures. The reaction scheme is suitable for oxidation-sensitive moieties including amino acids.

中文翻译:


N-末端甘氨酰异羟肟酸的Lossen重排诱导的分子内氧化还原反应合成N-乙醛酰肽



已经开发出一种无氧化剂合成 N-乙醛酰肽的方法,该方法利用 N 末端甘氨酰异羟肟酸残基的 Lossen 重排。合成通过分子内氧化还原机制进行,产生乙醛酰肽,然后对其进行各种肽环化程序。该反应方案适用于包括氨基酸在内的氧化敏感部分。
更新日期:2024-05-13
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