A self-immolative
bioorthogonal conditionally cleavable linker
based on Grob fragmentation is described. It is derived from 1,3-aminocyclohexanols
and allows the release of sulfonate-containing compounds in aqueous
media. Modulation of the amine p
K
a
promotes
fragmentation even at slightly acidic pH, a common feature of several
tumor environments. The Grob fragmentation can also occur under physiological
conditions in living cells, highlighting the potential bioorthogonal
applicability of this reaction.
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