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Selective N-terminal acylation of peptides and proteins with a Gly-His tag sequence.

Abstract：

:Methods for site-selective chemistry on proteins are in high demand for the synthesis of chemically modified biopharmaceuticals, as well as for applications in chemical biology, biosensors and more. Inadvertent N-terminal gluconoylation has been reported during expression of proteins with an N-terminal His tag. Here we report the development of this side-reaction into a general method for highly selective N-terminal acylation of proteins to introduce functional groups. We identify an optimized N-terminal sequence, GHHHn- for the reaction with gluconolactone and 4-methoxyphenyl esters as acylating agents, facilitating the introduction of functionalities in a highly selective and efficient manner. Azides, biotin or a fluorophore are introduced at the N-termini of four unrelated proteins by effective and selective acylation with the 4-methoxyphenyl esters. This Gly-Hisn tag adds the unique capability for highly selective N-terminal chemical acylation of expressed proteins. We anticipate that it can find wide application in chemical biology and for biopharmaceuticals.

journal_name

Nat Commun

journal_title

Nature communications

authors

Martos-Maldonado MC,Hjuler CT,Sørensen KK,Thygesen MB,Rasmussen JE,Villadsen K,Midtgaard SR,Kol S,Schoffelen S,Jensen KJ

doi

10.1038/s41467-018-05695-3

subject

Has Abstract

pub_date

2018-08-17 00:00:00

pages

3307

issue

1

issn

2041-1723

pii

10.1038/s41467-018-05695-3

journal_volume

9

pub_type

杂志文章

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