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Mal-Dap(Boc)-Val-Cit-PAB-PNP
Chemical name: N-alpha-Maleimido-N-beta-t-butyloxycarbonyl-L-2,3-diaminopropionyl-valyl-citrullyl-(4-aminobenzyl)-(4-nitrophenyl)-carbonate // Synonyms: Mal-Dap(Boc)-Val-Cit-PAB-pNC, tert-butyl(S)-2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-3-((S)-3-methyl-1-((S)-1-(4-(((4-nitrophenoxy)carbonyloxy)methyl)phenylamino)-1-oxo-5-ureidopentan-2-ylamino)-1-o xobutan-2-ylamino)-3-oxopropylcarbamate
- Product code:ADC1090
- CAS No.:2281797-57-5
- Formula:C37H46N8O13
- Molecular weight:810.81 g/mol
from $312.50
description
Linker for Antibody-Drug-Conjugation (ADC). The Val-Cit will specifically be cleaved by catepsin B. As this enzyme is only present in the lysosome the ACD payload will be release in the cell, only. MAL-Dap(Boc) building blocks are ideal tools for persistent conjugation with thiol groups: After removal of the Boc protecting group and conjugation with the mercaptane function, the free methylamino side chain will open the maleimide ring under aqueous conditions. While the conjugation reaction between thiol and cyclic maleimide is reversible, it turns completely stable in the open ring structure. This becomes particularly important in the formation of conjugates with high value components.
Please note the patent WO2013173337 for use of this compound in commercial applications, particular for antibody-drug conjugates.
references
Laurent Ducry (ed.), Antibody-Drug Conjugates, Methods in Molecular Biology, vol. 1045, DOI 10.1007/978-1-62703-541-5_5, # Springer Science+Business Media, LLC 2013.
Self-hydrolyzing maleimides improve the stability and pharmacological properties of antibody-drug conjugates; R.P. Lyon, J.R. Setter, T.D. Bovee, S.O. Doronia, J.H. Hunter, M.E. Anderson, C.L. Balasubramanian, S.M. Duniho, C.I. Leiske, F. Li, P.D. Senter; Nature Biotechnology 2014; 32(10): 1059-1062. DOI:10.1038/nbt.2968.
WO2013173337
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