2.0 2012-07-30 14:55:17 -0600 2015-06-03 17:21:08 -0600 ECMDB21313 M2MDB001715 Butanesulfonate Butanesulfonate is a member of the chemical class known as Sulfonic Acids. These are compounds containing the sulfonic acid group, which has the general structure RS(=O)2OH (R = H). 1-Butane sulfonate 1-Butane sulfonic acid 1-Butane sulphonate 1-Butane sulphonic acid 1-Butanesulfonate 1-Butanesulfonic acid 1-Butanesulphonate 1-Butanesulphonic acid Butane-1-sulfonate Butane-1-sulfonic acid Butane-1-sulphonate Butane-1-sulphonic acid Butanesulfonate Butanesulfonic acid Butanesulphonate Butanesulphonic acid N-Butyl-1-sulfonate N-Butyl-1-sulfonic acid N-Butyl-1-sulphonate N-Butyl-1-sulphonic acid C4H9O3S 137.177 137.027239844 butane-1-sulfonate 1-butanesulfonate CCCCS([O-])(=O)=O InChI=1S/C4H10O3S/c1-2-3-4-8(5,6)7/h2-4H2,1H3,(H,5,6,7)/p-1 QDHFHIQKOVNCNC-UHFFFAOYSA-M Cytosol Extra-organism Periplasm logp 0.32 ALOGPS logs -0.52 ALOGPS solubility 4.67e+01 g/l ALOGPS logp 0.52 ChemAxon pka_strongest_acidic -0.87 ChemAxon iupac butane-1-sulfonate ChemAxon average_mass 137.177 ChemAxon mono_mass 137.027239844 ChemAxon smiles CCCCS([O-])(=O)=O ChemAxon formula C4H9O3S ChemAxon inchi InChI=1S/C4H10O3S/c1-2-3-4-8(5,6)7/h2-4H2,1H3,(H,5,6,7)/p-1 ChemAxon inchikey QDHFHIQKOVNCNC-UHFFFAOYSA-M ChemAxon polar_surface_area 57.2 ChemAxon refractivity 29.41 ChemAxon polarizability 13.12 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 3 ChemAxon donor_count 0 ChemAxon physiological_charge -1 ChemAxon formal_charge -1 ChemAxon sulfur metabolism (butanesulfonate) The sulfur metabolism pathway starts in three possible ways. The first is the uptake of sulfate through an active transport reaction via a sulfate transport system containing an ATP-binding protein which hydrolyses ATP. Sulfate is converted by the sulfate adenylyltransferase enzymatic complex to adenosine phosphosulfate through the addition of adenine from a molecule of ATP, along with one phosphate group. Adenosine phosphosulfate is further converted to phoaphoadenosine phosphosulfate through an ATP hydrolysis and dehydrogenation reaction by the adenylyl-sulfate kinase. Phoaphoadenosine phosphosulfate is finally dehydrogenated and converted to sulfite by phosphoadenosine phosphosulfate reductase. This reaction requires magnesium, and adenosine 3',5'-diphosphate is the bi-product. A thioredoxin is also oxidized. Sulfite can also be produced from the dehydrogenation of cyanide along with the conversion of thiosulfate to thiocyanate by the thiosulfate sulfurtransferase enzymatic complex. Sulfite next undergoes a series of reactions that lead to the production of pyruvic acid, which is a precursor for pathways such as gluconeogenesis. The first reaction in this series is the conversion of sulfite to hydrogen sulfide through hygrogenation and the deoxygenation of sulfite to form a water molecule. The reaction is catalyzed by the sulfite reductase [NADPH] flavoprotein alpha and beta components. Siroheme, 4Fe-4S, flavin mononucleotide, and FAD function as cofactors or prosthetic groups. Hydrogen sulfide next undergoes dehydrogenation in a reversible reaction to form L-Cysteine and acetic acid, via the cysteine synthase complex and the coenzyme pyridoxal 5'-phosphate. L-Cysteine is dehydrogenated and converted to 2-aminoacrylic acid (a bronsted acid) and hydrogen sulfide(which may be reused) by a larger enzymatic complex composed of cysteine synthase A/B, protein malY, cystathionine-β-lyase, and tryptophanase, along with the coenzyme pyridoxal 5'-phosphate. 2-aminoacrylic acid isomerizes to 2-iminopropanoate, which along with a water molecule and a hydrogen ion is lastly converted to pyruvic acid and ammonium in a spontaneous fashion. The second possible initial starting point for sulfur metabolism is the import of taurine(an alternate sulfur source) into the cytoplasm via the taurine ABC transporter complex. Taurine, oxoglutaric acid, and oxygen are converted to sulfite by the alpha-ketoglutarate-dependent taurine dioxygenase. Carbon dioxide, succinic acid, and aminoacetaldehyde are bi-products of this reaction. Sulfite next enters pyruvic acid synthesis as already described. The third variant of sulfur metabolism starts with the import of an alkyl sulfate, in this case 1-butanesulfonate, into the cytoplasm via an aliphatic sulfonate ABC transporter complex which hydrolyses ATP. 1-butanesulfonate is dehydrogenated and along with oxygen is converted to sulfite and betaine aldehyde by the FMNH2-dependent alkanesulfonate monooxygenase enzyme. Water and flavin mononucleotide(which is used in a subsequent reaction as a prosthetic group) are also produced. Sulfite is next converted to pyruvic acid by the process already described. PW000923 Metabolic Specdb::NmrOneD 252048 Specdb::NmrOneD 252049 Specdb::NmrOneD 252050 Specdb::NmrOneD 252051 Specdb::NmrOneD 252052 Specdb::NmrOneD 252053 Specdb::NmrOneD 252054 Specdb::NmrOneD 252055 Specdb::NmrOneD 252056 Specdb::NmrOneD 252057 Specdb::NmrOneD 252058 Specdb::NmrOneD 252059 Specdb::NmrOneD 252060 Specdb::NmrOneD 252061 Specdb::NmrOneD 252062 Specdb::NmrOneD 252063 Specdb::NmrOneD 252064 Specdb::NmrOneD 252065 Specdb::NmrOneD 252066 Specdb::NmrOneD 252067 Specdb::MsMs 25808 Specdb::MsMs 25809 Specdb::MsMs 25810 Specdb::MsMs 32366 Specdb::MsMs 32367 Specdb::MsMs 32368 3704751 2936321 61911 CPD-3744 Alkanesulfonate monooxygenase P80645 SSUD_ECOLI ssuD http://ecmdb.ca/proteins/P80645.xml Putative aliphatic sulfonates transport permease protein ssuC P75851 SSUC_ECOLI ssuC http://ecmdb.ca/proteins/P75851.xml Taurine transport system permease protein tauC Q47539 TAUC_ECOLI tauC http://ecmdb.ca/proteins/Q47539.xml Putative aliphatic sulfonates-binding protein P75853 SSUA_ECOLI ssuA http://ecmdb.ca/proteins/P75853.xml Taurine import ATP-binding protein TauB Q47538 TAUB_ECOLI tauB http://ecmdb.ca/proteins/Q47538.xml Taurine-binding periplasmic protein Q47537 TAUA_ECOLI tauA http://ecmdb.ca/proteins/Q47537.xml Aliphatic sulfonates import ATP-binding protein SsuB P0AAI1 SSUB_ECOLI ssuB http://ecmdb.ca/proteins/P0AAI1.xml Putative aliphatic sulfonates transport permease protein ssuC P75851 SSUC_ECOLI ssuC http://ecmdb.ca/proteins/P75851.xml Taurine transport system permease protein tauC Q47539 TAUC_ECOLI tauC http://ecmdb.ca/proteins/Q47539.xml Putative aliphatic sulfonates-binding protein P75853 SSUA_ECOLI ssuA http://ecmdb.ca/proteins/P75853.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml Taurine import ATP-binding protein TauB Q47538 TAUB_ECOLI tauB http://ecmdb.ca/proteins/Q47538.xml Taurine-binding periplasmic protein Q47537 TAUA_ECOLI tauA http://ecmdb.ca/proteins/Q47537.xml Aliphatic sulfonates import ATP-binding protein SsuB P0AAI1 SSUB_ECOLI ssuB http://ecmdb.ca/proteins/P0AAI1.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml Adenosine triphosphate + Water + Butanesulfonate > ADP + Butanesulfonate + Hydrogen ion + Phosphate Adenosine triphosphate + Water + Butanesulfonate > ADP + Butanesulfonate + Hydrogen ion + Phosphate Butanesulfonate + FMNH + Oxygen > Butanal + Flavin Mononucleotide + Hydrogen ion + Water + Sulfite RXN0-6973 Butanesulfonate + Oxygen + FMNH > Butanal + Sulfite + Water + Flavin Mononucleotide + Hydrogen ion RXN0-6973 Butanesulfonate + Oxygen + FMNH2 > Hydrogen ion + Water + Sulfite + Flavin Mononucleotide + Betaine aldehyde + Sulfite PW_R003467 Adenosine triphosphate + Water + Butanesulfonate > Adenosine diphosphate + Phosphate + Hydrogen ion + Butanesulfonate + ADP PW_RCT000147 Adenosine triphosphate + Water + Butanesulfonate > Adenosine diphosphate + Phosphate + Hydrogen ion + Butanesulfonate + ADP PW_RCT000147