Site-specific modification of peptides and proteins is ak ey aspect of protein engineering.W ed eveloped am ethod for modification of the Nterminus of proteins using 1H-1,2,3-triazole-4-carbaldehyde( TA4C) derivatives, which can be prepared in one step. The N-terminal specific labelingo fb ioactive peptides and proteins with the TA4C derivatives proceeds under mild reactionc onditions in excellent conversion (angiotensinI: 92 %, ribonuclease A: 90 %). This method enables site-specific conjugation of various functional molecules such as fluorophores,b iotin, and polyethylene glycol attached to the triazole ring to the Nterminus. Furthermore, af unctional molecule modified with ap rimary amine moiety can be directly converted into aT A4C derivativethrough aDimroth rearrangement reaction with 1-(4-nitrophenyl)-1H-1,2,3-triazole-4-carbaldehyde. This methodc an be used to obtain N-terminal-modifiedp roteins via only two steps:1 )convenient preparation of aT A4C derivativew ith af unctional group and 2) modification of the Nterminus of the protein with the TA4C derivative.
Hitting the target of the N terminus for protein modification is of paramount importance for constructing protein conjugates. An N‐terminal‐targeting molecule, 1H‐1,2,3‐triazole‐4‐carbaldehyde (T4AC) represented by an arrow in the Kyudo‐styled cover artwork, enables specific modification of the protein. The T4AC molecule can be prepared from structures with an amine group by a single step Dimroth rearrangement. This method provides the N‐terminal protein modification with a wide variety of functional molecules in a two‐step process. More information can be found in the communication by A. Onoda, T. Hayashi, et al. on page 1274 in Issue 9, 2020 (DOI: 10.1002/cbic.201900692).
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