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Aldehyde-catalysed carboxylate exchange in α-amino acids with isotopically labelled CO2
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Aldehyde-catalysed carboxylate exchange in α-amino acids with isotopically labelled CO2
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Journal Article
Aldehyde-catalysed carboxylate exchange in α-amino acids with isotopically labelled CO2
2022
Overview
The isotopic labelling of small molecules is integral to drug development and for understanding biochemical processes. The preparation of carbon-labelled α-amino acids remains difficult and time consuming, with established methods involving label incorporation at an early stage of synthesis. This explains the high cost and scarcity of C-labelled products and presents a major challenge in
11
C applications (
11
C
t
1/2
= 20 min). Here we report that aldehydes catalyse the isotopic carboxylate exchange of native α-amino acids with *CO
2
(* = 14, 13, 11). Proteinogenic α-amino acids and many non-natural variants containing diverse functional groups undergo labelling. The reaction probably proceeds via the trapping of *CO
2
by imine-carboxylate intermediates to generate iminomalonates that are prone to monodecarboxylation. Tempering catalyst electrophilicity was key to preventing irreversible aldehyde consumption. The pre-generation of the imine carboxylate intermediate allows for the rapid and late-stage
11
C-radiolabelling of α-amino acids in the presence of [
11
C]CO
2
.
Carbon-labelled α-amino acids are valuable compounds in drug development and nuclear medicine, but are difficult and time consuming to prepare. Now, an aldehyde-catalysed method has been developed for the direct C1-labelling of α-amino acids using *CO
2
(* = 14, 13, 11), providing access to many proteinogenic and non-natural labelled α-amino acids.
Publisher
Nature Publishing Group UK,Nature Publishing Group
Subject
