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Non-Canonical Amino Acid Which Rapidly Reacts with Maleimide to Allow Site-Specific Modifications into Antibodies
N6-[(Spiro[2.4]hept-4,6-dien-1-ylmethoxy)carbonyl]-L-lysine (1) is useful for the preparation of site-specifically modified antibody-drug conjugates (ADCs).1) The spiroheptadiene (SCp) moiety of 1, introduced into a specific site of the protein by genetic code expansion, selectively reacts with maleimide moiety at a rate of 1.8-5.4 M-1 s-1 via the Diels-Alder reaction.2) ADCs generated by reacting 1-incorporated antibodies with drug-conjugated maleimides exhibit better stability and efficacy than cysteine-maleimide conjugates both in mouse serum and in vivo.
Related Products
- H1840
- N6-[(Spiro[2.4]hept-4,6-dien-1-ylmethoxy)carbonyl]-L-lysine
- T4126
- N-(4E)-TCO-L-lysine
- A3550
- L-Azidohomoalanine
Related Product Category Pages
References
- 1) Click chemistry in the synthesis of antibody-drug conjugates
- 2) A Reactive Antibody Platform for One-Step Production of Antibody-Drug Conjugates through a Diels-Alder Reaction with Maleimide
