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Rapid additive-free selenocystine-selenoester peptide ligation.
Mitchell, Nicholas J; Malins, Lara R; Liu, Xuyu; Thompson, Robert E; Chan, Bun; Radom, Leo; Payne, Richard J.
Afiliação
  • Mitchell NJ; School of Chemistry, The University of Sydney , Sydney, NSW 2006, Australia.
  • Malins LR; School of Chemistry, The University of Sydney , Sydney, NSW 2006, Australia.
  • Liu X; School of Chemistry, The University of Sydney , Sydney, NSW 2006, Australia.
  • Thompson RE; School of Chemistry, The University of Sydney , Sydney, NSW 2006, Australia.
  • Chan B; School of Chemistry, The University of Sydney , Sydney, NSW 2006, Australia.
  • Radom L; School of Chemistry, The University of Sydney , Sydney, NSW 2006, Australia.
  • Payne RJ; School of Chemistry, The University of Sydney , Sydney, NSW 2006, Australia.
J Am Chem Soc ; 137(44): 14011-4, 2015 Nov 11.
Article em En | MEDLINE | ID: mdl-26487084
ABSTRACT
We describe an unprecedented reaction between peptide selenoesters and peptide dimers bearing N-terminal selenocystine that proceeds in aqueous buffer to afford native amide bonds without the use of additives. The selenocystine-selenoester ligations are complete in minutes, even at sterically hindered junctions, and can be used in concert with one-pot deselenization chemistry. Various pathways for the transformation are proposed and probed through a combination of experimental and computational studies. Our new reaction manifold is also showcased in the total synthesis of two proteins.
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Texto completo: 1 Base de dados: MEDLINE Assunto principal: Peptídeos / Proteínas de Bactérias / Corismato Mutase / Compostos Organosselênicos / Cistina Idioma: En Ano de publicação: 2015 Tipo de documento: Article
Texto completo
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Buscar no Google

Texto completo: 1 Base de dados: MEDLINE Assunto principal: Peptídeos / Proteínas de Bactérias / Corismato Mutase / Compostos Organosselênicos / Cistina Idioma: En Ano de publicação: 2015 Tipo de documento: Article