Non-Canonical Amino Acid for Site-Specific Antibody Modification via Diels-Alder Reaction with Maleimide

N6-[(Spiro[2.4]hept-4,6-dien-1-ylmethoxy)carbonyl]-L-lysine (1) is useful for preparing site-specifically modified antibody-drug conjugates (ADCs).¹) The spiroheptadiene (SCp) moiety of 1, introduced into a specific protein site by genetic code expansion, selectively reacts with maleimide 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 in both mouse serum and in vivo.²)

Related products

• TCI H1840 2253967-13-2 N6-[(Spiro[24]hepta-4,6-dien-1-ylmethoxy)carbonyl]-L-lysine

References

1. Click chemistry in the synthesis of antibody-drug conjugates. R. Dudchak et al., Bioorg Chem. 2024, 143, 106982.
2. A Reactive Antibody Platform for One-Step Production of Antibody-Drug Conjugates through a Diels-Alder Reaction with Maleimide. A. H. St. Amant et al., R. J. Christie, Bioconjugate Chem. 2019, 30, 2340.

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Source

• TCI Product Highlights: www.tcichemicals.com/ID/en/product/tci-topics/ProductHighlights_20240422
• TCI product page H1840: tcichemicals.com/ID/en/p/H1840

For research and laboratory use only, not for human consumption.