Rapid sodium periodate cleavage of an unnatural amino acid enables unmasking of a highly reactive α-oxo aldehyde for protein bioconjugation

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Research output: Contribution to journal › Article › peer-review

Full text download(s)

Rapid sodium periodate cleavage of an unnatural amino acid enables unmasking of a highly reactive α-oxo aldehyde for protein bioconjugation
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Published copy (DOI)

10.1039/d0ob00972e

Author(s)

Robin Brabham
Tessa Keenan
Annika Husken
Jacob Bilsborrow
Ryan McBerney
Vajinder Kumar
W. Bruce Turnbull
Martin Anthony Fascione

Department/unit(s)

Chemistry

Publication details

Journal	Organic and Biomolecular Chemistry
Date	Accepted/In press - 14 May 2020
Date	E-pub ahead of print (current) - 14 May 2020
Early online date	14/05/20
Original language	English

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