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Dialdehydes lead to exceptionally fast bioconjugations at neutral pH by virtue of a cyclic intermediate

Abstract:

One of the open challenges in chemical biology is to identify reactions that proceed with large rate constants at neutral pH values. As shown here, dialdehydes react with O-alkylhydroxylamines at rates of 500 M(-1) s(-1) at neutral pH 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 appl...

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Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.1002/anie.201406132

Authors


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Institution:
University of Oxford
Division:
MSD
Department:
NDM
Role:
Author
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Role:
Author
ORCID:
0000-0002-3672-8699
Publisher:
Wiley Publisher's website
Journal:
Angewandte Chemie International Edition Journal website
Volume:
53
Issue:
41
Pages:
10928-10931
Place of publication:
Germany
Publication date:
2014-08-27
DOI:
EISSN:
1521-3773
ISSN:
1433-7851
Pmid:
25164607
Language:
English
Keywords:
Pubs id:
561249
Local pid:
pubs:561249
Deposit date:
2020-10-26

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