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. 2020 Jan 28;5(5):2069–2080. doi: 10.1021/acsomega.9b04078

Table 1. Chemical Reagents Commonly Used to Target Amino Acid Residues of Membrane Transport Proteins.

reagent type target AA
N-ethylmaleimide (NEM) maleimides Cys
N-pyrene maleimide    
N-pyrroloisomaleimide    
N,N′-phenylene-bismaleimides    
N-(4-dimethylamino-3,5-dinitrophenyl)-maleimde    
N,N′-hexamethylene-bismaleimide    
4-chloroacetylphenylmaleimide    
4-azidophenylmaleimide    
iodoacetate alkylating reagents Cys
iodoacetamide    
bromoacetate    
chloroacetate    
bromopyruvate    
ethylene oxide and -imine    
methyl iodide    
dimethylsulfate    
fluorodinitrobenzene (FDNB) arylating reagents Cys
chlorodinitrobenzene (CDNB)    
Ag +, Cu+, Au+, Hg2+, Pb2+, Cu2+, Cd2+, Zn2+, Sb3+ metal ions Cys
p-chloromercuribenzoate (pCMB) organic mercurials Cys
p-chloromercuriphenylsulfonate (pCMBS)    
phenylmercuryacetate    
methylmercury iodide    
methylmercury bromide    
O-(3-hydroxymercuri-2-methoxypropyl)carbamylphenoxyacetate (mersalyl)    
chloromercurinitrophenols    
S-mercuric N-dansyl cysteine    
arsenite arsenic reagents Cys
arsenoxides    
iodine oxidizing reagents Cys
ferricyanide    
tetrathionate    
Na2S406    
H2O2    
sulfoxides    
benzofuroxan    
dansyl chloride    
thiocyanogen    
(SCN)2    
tetranitromethane    
1,1′-azobis(N,N-dimethylformamide) (diamide)    
5,5′-dithio-bis(2-nitrobenzoic acid) (DTNB) disulfides Cys
n-propyl-2-pyridyl disulfide    
N-succinimidyl-3-(2-pyridyldithio)proprionate (SPDP)    
β-hydroxyethyl-2,4-dinitrophenyl disulfide    
oxidized glutathione (GSSG)    
cystamine    
cystamine monosulfoxide    
di-N-(2-nitro-4-azidophenyl)-cystamine-S,S-dioxide (DNCO)    
sodium (2-sulfonatoethyl)methanethiosulfonate (MTSES) methanethiosulfonates Cys
2-aminoethyl methanethiosulfonate hydrobromide (MTSEA)    
(2-(trimethylammonium)ethyl)methanethiosulfonate bromide (MTSET)    
methyl methanethiosulfonate (MMTS)    
1-ethyl-3-(3′-dimethylan1inopropyl)carbodiimide (EDC) various Asp/Glu
2-hydroxy-5-nitrobenzyl bromide (Koshland’s Reagent)   Trp
sulfo-NHS-SS-biotin   Lys
4,4′-diisothiocyanatostilbene-2,2′-disulfonate (DIDS)   Lys
4-acetamido-4′-isothiocyanato-stilben-2,2′-disulfonate (SITS)   Lys
pyridoxal phosphate (PLP)   Lys
Woodward’s reagent K (2-ethyl-5-phenylisoxazolium-3′-sulfonate)   Asp/Glu
phenylglyoxal   Arg
phenylmethylsulfonyl fluoride (PMSF)   Ser
diethyl pyrocarbonate (DEPC)   His
N-bromosuccinimide (NBS)   Trp