Rapid sodium periodate cleavage of an unnatural amino acid enables unmasking of a highly reactive α-oxo aldehyde for protein bioconjugation†
Robin L.
Brabham, 
‡a
Tessa
Keenan,
‡a
Jacob
Bilsborrow,
a
W. Bruce
Turnbull
b
and
Martin A.
Fascione
*a
‡a
Tessa
Keenan,
‡a
Jacob
Bilsborrow,
a
W. Bruce
Turnbull
b
and
Martin A.
Fascione
*a
Abstract
The α-oxo aldehyde is a highly reactive aldehyde for which many protein bioconjugation strategies exist. Here, we explore the genetic incorporation of a threonine-lysine dipeptide into proteins, harbouring a “masked” α-oxo aldehyde that is rapidly unveiled in four minutes. The reactive aldehyde could undergo site-specific protein modification by SPANC ligation.
- This article is part of the themed collections: Editor’s Collection, Chemical Biology in OBC and Methodology development for protein modifications
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