Table 4 Selected apparent second order rate constants for reaction of HOCl with amino acid side chains, backbone amides and models of these structures

Data from [278,281,282].

Side chain (model compound examined)Apparent second order rate constant (M−1·s−1)
Cysteine side chain (cysteine)3.6×108
Glutathione (GSH)1.2×108
Methionine side chain (N-acetyl-Met-OMe)3.4×107
Cystine disulfide (3,3′-dithiodipropionic acid)1.6×105
Histidine side chain (4-imidazoleacetic acid)1.2×105
α-Amino group (Gly)1.0×105
Lysine side-chain amine (N-α-acetyl-Lys)7.9×103
Tryptophan side chain (N-acetyl-Trp)7.8×103
Tyrosine (N-acetyl-Tyr)47
Arginine side chain (ethyl guanidine)19
Amide bond [Cyclo-(Gly)2]25
Amide bond [Cyclo-(Ala)2]8.2
Glutamine/asparagine (propionamide)0.041