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Synfacts 2020; 16(06): 0741
DOI: 10.1055/s-0040-1707536
Peptide Chemistry
© Georg Thieme Verlag Stuttgart · New York

Chemical Ligation to Synthesize N-Hydroxy Peptides from O-Acyl Hydroxamic Acids

Contributor(s):
Hisahsi Yamamoto
,
Tomohiro Hattori
Braslau R. Axon JR, Lee B. University of California, Santa Cruz, USA
Synthesis of N-Hydroxy Peptides: Chemical Ligation of O-Acyl Hydroxamic Acids.

Org. Lett. 2000;
2: 1399-1401
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Further Information

Publication History

Publication Date:
15 May 2020 (online)

 
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Key words

chemical ligation - hydroxy peptides - O-acyl hydroxamic acids

Significance

Chemical ligation is an important bottleneck reaction in peptide chemistry. The ­authors have developed a synthesis of O-acyl hydroxamic acids, which can be converted into the corresponding N-hydroxy peptides.


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Comment

O-Acyl hydroxamic acids were prepared from amino acids and N-(tert-butyl)hydroxylamine. Furthermore, deprotection of an Fmoc group from the O-acyl hydroxamic acids with subsequent formation of a new peptide bond proceeds smoothly.


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