2.0 2012-05-31 14:27:57 -0600 2015-09-17 15:41:56 -0600 ECMDB20109 M2MDB000957 7,8-Diaminononanoate 7,8-diaminononanoate (or DAPA) is an intermediate in biotin biosynthesis. It is a substrate for Adenosylmethionine-8-amino-7-oxononanoate aminotransferase (or bioA). This enzyme catalyzes the transfer of the alpha-amino group from S-adenosyl-L-methionine (SAM) to 7-keto-8-aminopelargonic acid (KAPA) to form 7,8-diaminopelargonic acid (DAPA). The reaction is S-adenosyl-L-methionine + 8-amino-7-oxononanoate = S-adenosyl-4-methylthio-2-oxobutanoate + 7,8-diaminononanoate. DAPA is a simple intercalator, much like the widely studied 9-aminoacridine. (PMID 16180206; 16984394) (7R,8S)-7,8-diaminononanoate (7R,8S)-7,8-diaminononanoic acid 7,8-Diamino-Nonanoate 7,8-Diamino-Nonanoic Acid 7,8-Diaminononanoate 7,8-Diaminononanoic acid 7,8-Diaminopelargonate 7,8-Diaminopelargonic acid 7,8DANA DAPA Diaminononanoate Diaminononanoic acid DNN C9H19N2O2 187.264 187.14520144 7,8-diaminononanoic acid 7,8-diaminopelargonic acid 21738-21-6 CC(N)C(N)CCCCCC([O-])=O InChI=1S/C9H20N2O2/c1-7(10)8(11)5-3-2-4-6-9(12)13/h7-8H,2-6,10-11H2,1H3,(H,12,13)/p-1 KCEGBPIYGIWCDH-UHFFFAOYSA-M Cytosol logp -2.11 ALOGPS logs -1.58 ALOGPS solubility 4.94e+00 g/l ALOGPS logp -1.9 ChemAxon pka_strongest_acidic 4.73 ChemAxon pka_strongest_basic 9.97 ChemAxon iupac 7,8-diaminononanoic acid ChemAxon average_mass 187.264 ChemAxon mono_mass 187.14520144 ChemAxon smiles CC(N)C(N)CCCCCC([O-])=O ChemAxon formula C9H19N2O2 ChemAxon inchi InChI=1S/C9H20N2O2/c1-7(10)8(11)5-3-2-4-6-9(12)13/h7-8H,2-6,10-11H2,1H3,(H,12,13)/p-1 ChemAxon inchikey KCEGBPIYGIWCDH-UHFFFAOYSA-M ChemAxon polar_surface_area 89.34 ChemAxon refractivity 51.3 ChemAxon polarizability 21.87 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon Biotin metabolism Biotin (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. PW000762 ec00780 Metabolic Metabolic pathways eco01100 biotin biosynthesis from 7-keto-8-aminopelargonate PWY0-1507 Specdb::CMs 3470 Specdb::NmrOneD 305171 Specdb::NmrOneD 305172 Specdb::NmrOneD 305173 Specdb::NmrOneD 305174 Specdb::NmrOneD 305175 Specdb::NmrOneD 305176 Specdb::NmrOneD 305177 Specdb::NmrOneD 305178 Specdb::NmrOneD 305179 Specdb::NmrOneD 305180 Specdb::NmrOneD 305181 Specdb::NmrOneD 305182 Specdb::NmrOneD 305183 Specdb::NmrOneD 305184 Specdb::NmrOneD 305185 Specdb::NmrOneD 305186 Specdb::NmrOneD 305187 Specdb::NmrOneD 305188 Specdb::NmrOneD 305189 Specdb::NmrOneD 305190 Specdb::MsMs 28199 Specdb::MsMs 28200 Specdb::MsMs 28201 Specdb::MsMs 34757 Specdb::MsMs 34758 Specdb::MsMs 34759 Specdb::MsMs 3608344 Specdb::MsMs 3608345 Specdb::MsMs 3608346 Specdb::MsMs 3608347 Specdb::MsMs 3608348 Specdb::MsMs 3608349 652 632 C01037 2247 DIAMINONONANOATE Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. 17765195 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 Hoffmann, G. R., Yin, C. C., Terry, C. E., Ferguson, L. R., Denny, W. A. (2006). "Frameshift mutations induced by four isomeric nitroacridines and their des-nitro counterpart in the lacZ reversion assay in Escherichia coli." Environ Mol Mutagen 47:82-94. 16180206 Mann, S., Ploux, O. (2006). "7,8-Diaminoperlargonic acid aminotransferase from Mycobacterium tuberculosis, a potential therapeutic target. Characterization and inhibition studies." FEBS J 273:4778-4789. 16984394 Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A Putative dethiobiotin synthetase P0A6E9 BIOD2_ECOLI ynfK http://ecmdb.ca/proteins/P0A6E9.xml Adenosylmethionine-8-amino-7-oxononanoate aminotransferase P12995 BIOA_ECOLI bioA http://ecmdb.ca/proteins/P12995.xml Dethiobiotin synthetase P13000 BIOD_ECOLI bioD http://ecmdb.ca/proteins/P13000.xml 8-Amino-7-oxononanoate + S-Adenosylmethionine <> S-Adenosyl-4-methylthio-2-oxobutanoate + 7,8-Diaminononanoate R03231 DAPASYN-RXN Adenosine triphosphate + Carbon dioxide + 7,8-Diaminononanoate <> ADP + Dethiobiotin +3 Hydrogen ion + Phosphate R03182 DETHIOBIOTIN-SYN-RXN Adenosine triphosphate + 7,8-Diaminononanoate + Carbon dioxide <> ADP + Phosphate + Dethiobiotin R03182 S-Adenosylmethionine + 8-Amino-7-oxononanoate > S-Adenosyl-4-methylthio-2-oxobutanoate + 7,8-Diaminononanoate DAPASYN-RXN Carbon dioxide + 7,8-Diaminononanoate + Adenosine triphosphate > Hydrogen ion + Dethiobiotin + Phosphate + ADP DETHIOBIOTIN-SYN-RXN S-adenosyl-L-methionine + 8-Amino-7-oxononanoate > S-Adenosyl-4-methylthio-2-oxobutanoate + 7,8-Diaminononanoate Adenosine triphosphate + 7,8-Diaminononanoate + Carbon dioxide > ADP + Inorganic phosphate + Dethiobiotin 8-Amino-7-oxononanoate + S-adenosyl-L-methionine > a sulfurated [sulfur carrier] + 7,8-Diaminononanoate + 7,8-Diaminononanoate PW_R002497 7,8-Diaminononanoate + Adenosine triphosphate + Carbon dioxide + 7,8-Diaminononanoate > Dethiobiotin + Adenosine diphosphate + Phosphate + ADP PW_R002498 8 8-Amino-7-oxononanoate + S-Adenosylmethionine <> S-Adenosyl-4-methylthio-2-oxobutanoate +7 7,8-Diaminononanoate Adenosine triphosphate + Carbon dioxide + 7 7,8-Diaminononanoate <> ADP + Dethiobiotin +3 Hydrogen ion + Phosphate 8 8-Amino-7-oxononanoate + S-Adenosylmethionine <> S-Adenosyl-4-methylthio-2-oxobutanoate +7 7,8-Diaminononanoate Adenosine triphosphate + Carbon dioxide + 7 7,8-Diaminononanoate <> ADP + Dethiobiotin +3 Hydrogen ion + Phosphate