Acetylthiocholine
Synthetic substrate for the Ellman reaction (the free thiol product of reaction is detected colorimetrically with the DTNB reagent). Entry of reference human-ACHE. Acetylthiocholine is an agent used as a substrate in assays for cholinesterases, especially to discriminate among enzyme types.
General
Type : Acetate, Trimethylammonium, Choline ester, Chromogen
Chemical_Nomenclature : 2-acetylsulfanylethyl(trimethyl)azanium
Canonical SMILES : CC(=O)SCC[N+](C)(C)C
InChI : InChI=1S\/C7H16NOS\/c1-7(9)10-6-5-8(2,3)4\/h5-6H2,1-4H3\/q+1
InChIKey : GFFIJCYHQYHUHB-UHFFFAOYSA-N
Other name(s) : 2-(Thioacetyloxy)-N,N,N,-trimethylethanaminium (bromide or chloride) || S-Acetylthiocholine || 2ha5 || AC1L2GHM || Lopac-A-5626
Target
Structures : 2HA5, 2C4H, 2C58, 2C5G
Families : ACHE, BCHE, Cholinesterase, Cholinesterase-like
References (13)
| Title : Substrate and product trafficking through the active center gorge of acetylcholinesterase analyzed by crystallography and equilibrium binding - Bourne_2006_J.Biol.Chem_281_29256 |
| Author(s) : Bourne Y , Radic Z , Sulzenbacher G , Kim E , Taylor P , Marchot P |
| Ref : Journal of Biological Chemistry , 281 :29256 , 2006 |
| Abstract : |
| PubMedSearch : Bourne_2006_J.Biol.Chem_281_29256 |
| PubMedID: 16837465 |
| Gene_locus related to this paper: mouse-ACHE |
| Title : Structural insights into substrate traffic and inhibition in acetylcholinesterase - Colletier_2006_EMBO.J_25_2746 |
| Author(s) : Colletier JP , Fournier D , Greenblatt HM , Stojan J , Sussman JL , Zaccai G , Silman I , Weik M |
| Ref : EMBO Journal , 25 :2746 , 2006 |
| Abstract : |
| PubMedSearch : Colletier_2006_EMBO.J_25_2746 |
| PubMedID: 16763558 |
| Gene_locus related to this paper: torca-ACHE |
| Title : Substrate binding to the peripheral site of acetylcholinesterase initiates enzymatic catalysis. Substrate inhibition arises as a secondary effect - Szegletes_1999_Biochemistry_38_122 |
| Author(s) : Szegletes T , Mallender WD , Thomas PJ , Rosenberry TL |
| Ref : Biochemistry , 38 :122 , 1999 |
| Abstract : |
| PubMedSearch : Szegletes_1999_Biochemistry_38_122 |
| PubMedID: 9890890 |
| Title : Electrostatic influence on the kinetics of ligand binding to acetylcholinesterase. Distinctions between active center ligands and fasciculin - Radic_1997_J.Biol.Chem_272_23265 |
| Author(s) : Radic Z , Kirchhoff PD , Quinn DM , McCammon JA , Taylor P |
| Ref : Journal of Biological Chemistry , 272 :23265 , 1997 |
| Abstract : |
| PubMedSearch : Radic_1997_J.Biol.Chem_272_23265 |
| PubMedID: 9287336 |
| Title : Cloning and expression of acetylcholinesterase from Bungarus fasciatus venom. A new type of cooh-terminal domain\; involvement of a positively charged residue in the peripheral site - Cousin_1996_J.Biol.Chem_271_15099 |
| Author(s) : Cousin X , Bon S , Duval N , Massoulie J , Bon C |
| Ref : Journal of Biological Chemistry , 271 :15099 , 1996 |
| Abstract : |
| PubMedSearch : Cousin_1996_J.Biol.Chem_271_15099 |
| PubMedID: 8662867 |
| Gene_locus related to this paper: bunfa-ACHE |
| Title : [Conformational differences in the sorption of choline ligands at the active site of acetylcholinesterase]. [Russian] - Shestakova_1995_Bioorg.Khim_21_323 |
| Author(s) : Shestakova NN , Rozengart EV |
| Ref : Bioorganicheskaia Khimiia , 21 :323 , 1995 |
| Abstract : |
| PubMedSearch : Shestakova_1995_Bioorg.Khim_21_323 |
| PubMedID: 7661856 |
| Title : Characterization of monoclonal antibodies that strongly inhibit Electrophorus electricus acetylcholinesterase - Remy_1995_Eur.J.Biochem_231_651 |
| Author(s) : Remy MH , Frobert Y , Grassi J |
| Ref : European Journal of Biochemistry , 231 :651 , 1995 |
| Abstract : |
| PubMedSearch : Remy_1995_Eur.J.Biochem_231_651 |
| PubMedID: 7649165 |
| Title : Acetylcholinesterase peripheral anionic site degeneracy conferred by amino acid arrays sharing a common core - Barak_1994_J.Biol.Chem_269_6296 |
| Author(s) : Barak D , Kronman C , Ordentlich A , Ariel N , Bromberg A , Marcus D , Lazar A , Velan B , Shafferman A |
| Ref : Journal of Biological Chemistry , 269 :6296 , 1994 |
| Abstract : |
| PubMedSearch : Barak_1994_J.Biol.Chem_269_6296 |
| PubMedID: 8119978 |
| Title : The back door hypothesis for product clearance in acetylcholinesterase challenged by site-directed mutagenesis - Kronman_1994_J.Biol.Chem_269_27819 |
| Author(s) : Kronman C , Ordentlich A , Barak D , Velan B , Shafferman A |
| Ref : Journal of Biological Chemistry , 269 :27819 , 1994 |
| Abstract : |
| PubMedSearch : Kronman_1994_J.Biol.Chem_269_27819 |
| PubMedID: 7961709 |
| Title : Electrostatic attraction by surface charge does not contribute to the catalytic efficiency of acetylcholinesterase - Shafferman_1994_EMBO.J_13_3448 |
| Author(s) : Shafferman A , Ordentlich A , Barak D , Kronman C , Ber R , Bino T , Ariel N , Osman R , Velan B |
| Ref : EMBO Journal , 13 :3448 , 1994 |
| Abstract : |
| PubMedSearch : Shafferman_1994_EMBO.J_13_3448 |
| PubMedID: 8062821 |
| Title : Three distinct domains in the cholinesterase molecule confer selectivity for acetyl- and butyrylcholinesterase inhibitors - Radic_1993_Biochemistry_32_12074 |
| Author(s) : Radic Z , Pickering NA , Vellom DC , Camp S , Taylor P |
| Ref : Biochemistry , 32 :12074 , 1993 |
| Abstract : |
| PubMedSearch : Radic_1993_Biochemistry_32_12074 |
| PubMedID: 8218285 |
| Title : Polymorphism of pseudocholinesterase in Torpedo marmorata tissues: comparative study of the catalytic and molecular properties of this enzyme with acetylcholinesterase - Toutant_1985_J.Neurochem_44_580 |
| Author(s) : Toutant JP , Massoulie J , Bon S |
| Ref : Journal of Neurochemistry , 44 :580 , 1985 |
| Abstract : |
| PubMedSearch : Toutant_1985_J.Neurochem_44_580 |
| PubMedID: 2578181 |
| Title : Hydrolysis of electronically and sterically defined substrates of acetylcholinesterase - |
| Author(s) : Hillman GR , Mautner HG |
| Ref : Biochemistry , 9 :2633 , 1970 |
| PubMedID: 5465354 |