Dialdehydes lead to exceptionally fast bioconjugations at neutral pH by virtue of a cyclic intermediate.
Angew Chem Int Ed Engl
; 53(41): 10928-31, 2014 Oct 06.
Article
em En
| MEDLINE
| ID: mdl-25164607
ABSTRACT
One of the open challenges in chemical biology is to identify reactions that proceed with large rate constants at neutral pHâ
values. As shown here, dialdehydes react with O-alkylhydroxylamines at rates of 500 M(-1) s(-1) at neutral pHâ
values in the absence of catalysts. The key to these conjugations is an unusually stable cyclic intermediate, which ultimately undergoes dehydration to yield an oxime. The scope and limitations of the method are outlined, as well as its application in bioconjugation and a mechanistic interpretation that will facilitate further developments of reactions with alkylhydroxylamines at low substrate concentrations.
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Base de dados:
MEDLINE
Assunto principal:
Aldeídos
/
Hidroxilaminas
Idioma:
En
Ano de publicação:
2014
Tipo de documento:
Article