期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 56, 期 44, 页码 13847-13851出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201707933
关键词
amino acids; boron; chemical ligation; ozonolysis; peptides
资金
- MEXT (Japan) program (Strategic Molecular and Materials Chemistry through Innovative Coupling Reactions) of Hokkaido University
- JSPS [15K13633, 15H03804, 17H06370, 16J01384]
- Grants-in-Aid for Scientific Research [16J01384, 15K13633, 15H03804] Funding Source: KAKEN
A concise synthesis of acylborons was achieved by ozonolysis of alkenyl MIDA (N-methyliminodiacetic acid) boronates. This reaction exhibits excellent functional-group tolerance and is applicable to various acyl MIDA boronates and potassium acyltrifluroborates (KATs) which could not be synthesized by previous methods. In addition, alpha-amino acylborons, which would be essential for peptide ligations, were prepared for the first time. The acylboron of l-alanine was obtained in high enantiopurity and found to be configurationally stable. Oligopeptide synthesis between the alpha-amino KATs and amino acid in dilute aqueous media was studied.
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