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Bioconjugation via Hetero-Selective Clamping of Two Different Amines with ortho-Phthalaldehyde.

Xin ChuBo LiHao-Yang LiuXiaowei SunXiaochen YangGang HeChuanzheng ZhouWeimin XuanShu-Lin LiuGong Chen
Published in: Angewandte Chemie (International ed. in English) (2022)
Amino groups are common in both natural and synthetic compounds and offer a very attractive class of endogenous handles for bioconjugation. However, the ability to differentiate two types of amino groups and join them with high hetero-selectivity and efficiency in a complex setting remains elusive. Herein, we report a new method for bioconjugation via one-pot chemoselective clamping of two different amine nucleophiles using a simple ortho-phthalaldehyde (OPA) reagent. Various α-amino acids, aryl amines, and secondary amines can be crosslinked to the ϵ-amino side chain of lysine on peptides or proteins with high efficiency and hetero-selectivity. This method offers a simple and powerful means to crosslink small molecule drugs, imaging probes, peptides, proteins, carbohydrates, and even virus particles without any pre-functionalization.
Keyphrases
  • small molecule
  • amino acid
  • high efficiency
  • protein protein
  • high resolution
  • fluorescence imaging
  • single molecule
  • living cells
  • mass spectrometry
  • drug induced