Triazolecarbaldehyde Reagents for One-step N-Terminal Protein Modification*.
Summary of "Triazolecarbaldehyde Reagents for One-step N-Terminal Protein Modification*."
Site-specific modification of peptides and proteins is a key aspect of protein engineering. We developed a method for modification of the N-terminus of proteins using 1 H -1,2,3-triazole-4-carbaldehyde (TA4C) derivatives, which can be prepared in one step. The N-terminal specific labeling of bioactive peptides and proteins with the TA4C derivatives proceeds under mild reaction conditions in excellent conversion (angiotensin
I:
92%, ribonuclease
A:
90%). This method enables site-specific conjugation of various functional molecules such as fluorophores, biotin, and polyethylene glycol attached to the triazole ring to the N-terminus. Furthermore, a functional molecule modified with a primary amine moiety can be directly converted to a TA4C derivative through a Dimroth rearrangement reaction with 1-(4-nitrophenyl)-1 H -1,2,3-triazole-4-carbaldehyde. This method can be used to obtain N-terminal modified proteins via only two steps; (i) convenient preparation of a TA4C derivative with a functional group and (ii) modification of the N-terminus of the protein with the TA4C derivative.
Affiliation
Journal Details
This article was published in the following journal.
Name: Chembiochem : a European journal of chemical biology
ISSN: 1439-7633
Pages:
Links
- PubMed Source: http://www.ncbi.nlm.nih.gov/pubmed/31794069
- DOI: http://dx.doi.org/10.1002/cbic.201900692
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