2.02015-09-08 17:49:57 -06002015-09-08 17:49:57 -0600ECMDB24186M2MDB006303a sulfurated [sulfur carrier]a Sulphurated [sulphur carrier]C2H630.06930.046950192ethaneethaneCCInChI=1S/C2H6/c1-2/h1-2H3OTMSDBZUPAUEDD-UHFFFAOYSA-Nlogp1.44logs0.38solubility7.26e+01 g/llogp1.35iupacethaneaverage_mass30.069mono_mass30.046950192smilesCCformulaC2H6inchiInChI=1S/C2H6/c1-2/h1-2H3inchikeyOTMSDBZUPAUEDD-UHFFFAOYSA-Npolar_surface_area0refractivity11polarizability4.46rotatable_bond_count0acceptor_count0donor_count0physiological_charge0formal_charge0Biotin metabolismBiotin (vitamin H or vitamin B7) is the essential cofactor of biotin-dependent carboxylases, such as pyruvate carboxylase and acetyl-CoA carboxylase.In E. coli and many organisms, pimelate thioester is derived from malonyl-ACP. The pathway starts with a malonyl-[acp] interacting with S-adenosylmethionine through a biotin synthesis protein BioC resulting in a S-adenosylhomocysteine and a malonyl-[acp] methyl ester. The latter compound is then involved in the synthesis of a 3-ketoglutaryl-[acp] methyl ester through a 3-oxoacyl-[acyl-carrier-protein] synthase. The compound 3-ketoglutaryl-[acp] methyl ester is reduced by a NADPH mediated 3-oxoacyl-[acyl-carrier-protein] reductase resulting in a 3R-hydroxyglutaryl-[acp] methyl ester. This compound is then dehydrated through ad (3R)-hydroxymyristoyl-[acp] dehydratase producing a enoylglutaryl-[acp] methyl ester. This compound is then reduced through a NADPH mediated enoyl-acp-reductase [NADH] resulting in a glutaryl-[acp] methyl ester. This compound interacts with a malonyl-[acp] through a 3-oxoacyl-[acp] synthase 2 resulting in a 3-ketopimeloyl [acp] methyl ester. This compound is then reduced through a NADPH 3-oxoacyl [acp] reductase producing a 3-hydroxypimeloyl-[acp] methyl ester and then dehydrated by (3R)-hydroxymyristoyl-[acp] dehydratase to produce a enoylpimeloyl-[acp] methyl ester. This compound is then reduced by a NADPH dependent enoyl-[acp]reductase resulting in a pimeloyl-[acp] methyl ester. This compound then reacts with water through a carboxylesterase resulting in a pimeloyl-[acp] and a methanol. The pimeloyl-acp reacts with L-alanine through a 8-amino-7-oxononanoate synthase resulting in 8-amino-7-oxononanoate which in turn reacts with S-adenosylmethionine through a 7,8 diaminonanoate transaminase resulting in a S-adenosyl-4-methylthio-2-oxobutanoate and 7,8 diaminononanoate. The latter compound is then dephosphorylated through a dethiobiotin synthetase resulting in a dethiobiotin. This compound interacts with a sulfurated[sulfur carrier), a hydrogen ion and a S-adenosylmethionine through a biotin synthase to produce Biotin and releasing l-methionine and a 5-deoxyadenosine.
Biotin is then metabolized by a bifunctional protein resulting in pyrophosphate and Biotinyl-5-AMP which in turn reacts with the same protein (bifunctional protein birA resulting ina biotin caroxyl carrying protein.This product then enters the fatty acid biosynthesis.
PW000762ec00780MetabolicSpecdb::CMs132177Specdb::CMs139911Specdb::NmrOneD330782Specdb::NmrOneD330783Specdb::NmrOneD330784Specdb::NmrOneD330785Specdb::NmrOneD330786Specdb::NmrOneD330787Specdb::NmrOneD330788Specdb::NmrOneD330789Specdb::NmrOneD330790Specdb::NmrOneD330791Specdb::NmrOneD330792Specdb::NmrOneD330793Specdb::NmrOneD330794Specdb::NmrOneD330795Specdb::NmrOneD330796Specdb::NmrOneD330797Specdb::NmrOneD330798Specdb::NmrOneD330799Specdb::NmrOneD330800Specdb::NmrOneD330801Specdb::MsMs29717Specdb::MsMs29718Specdb::MsMs29719Specdb::MsMs36275Specdb::MsMs36276Specdb::MsMs36277Specdb::MsMs2445139Specdb::MsMs2445140Specdb::MsMs2445141Specdb::MsMs2516745Specdb::MsMs2516746Specdb::MsMs2516747Adenosylmethionine-8-amino-7-oxononanoate aminotransferaseP12995BIOA_ECOLIbioAhttp://ecmdb.ca/proteins/P12995.xmlBiotin synthaseP12996BIOB_ECOLIbioBhttp://ecmdb.ca/proteins/P12996.xml8-amino-7-oxononanoate synthaseP12998BIOF_ECOLIbioFhttp://ecmdb.ca/proteins/P12998.xmla sulfurated [sulfur carrier] + L-Alanine + L-Alanine > 8-Amino-7-oxononanoate + Coenzyme A + Carbon dioxidePW_R0024968-Amino-7-oxononanoate + S-adenosyl-L-methionine > a sulfurated [sulfur carrier] + 7,8-Diaminononanoate + 7,8-DiaminononanoatePW_R002497Dethiobiotin + 2 S-adenosyl-L-methionine + 2 Hydrogen ion + a sulfurated [sulfur carrier] > Biotin +2 L-Methionine +2 5'-DeoxyadenosinePW_R002499