8-Amino-7-oxononanoic acid
8-Amino-7-oxononanoic acid is a precursor of 7,8-Diaminopelargonic acid (DAPA), and 7,8-diaminopelargonic acid aminotransferase (DAPA AT) is a potential drug target in Mycobacterium tuberculosis.
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Biochimie. 2009 Jul;91(7):826-34
Inhibition of 7,8-diaminopelargonic acid aminotransferase from Mycobacterium tuberculosis by chiral and achiral anologs of its substrate: biological implications.[Pubmed:
19345718 ]
7,8-Diaminopelargonic acid aminotransferase (DAPA AT), a potential drug target in Mycobacterium tuberculosis, transforms 8-Amino-7-oxononanoic acid (KAPA) into DAPA.
METHODS AND RESULTS:
We have designed an analytical method to measure the enantiomeric excess of KAPA, based on the derivatization of its amine function, by ortho-phtalaldehyde and N-acetyl-l-cysteine, followed by high pressure liquid chromatography separation. Using this methodology and enantiopure samples of KAPA it appeared that racemization of KAPA occurs rapidly (half-lives from 1 to 8 h) not only in 4 M HCl but more importantly in the usual pH range, from 7 to 9. Furthermore, we showed that racemic KAPA, and not enantiopure KAPA, was used in all previous studies. The only valid enantioselective synthesis of KAPA is that reported by Lucet et al. (1996) Tetrahedron: Asymmetry 7, 985-988. KAPA is produced as a pure (S)-enantiomer by KAPA synthase and by microbial production and DAPA AT only uses (S)-KAPA as substrate. However, (R)-KAPA is an inhibitor of this enzyme. It binds to the pyridoxal 5'-phosphate form (K(i1) = 5.9 +/- 0.2 microM) and to the pyridoxamine 5'-phosphate form (K(i2) = 1.7 +/- 0.2 microM) of M. tuberculosis DAPA AT.
CONCLUSIONS:
Molecular modeling showed that (R)-KAPA forms specific hydrogen bonds with T309 and the phosphate group of the cofactor of DAPA AT. Desmethyl-KAPA (8-amino-7-oxooctanoic acid), an achiral analog of KAPA, is also a potent inhibitor of M. tuberculosis DAPA AT.
This molecule binds to the enzyme in a similar way than (R)-KAPA with the following constants: K(i1) = 4.2 +/- 0.2 microM, and K(i2) = 0.9 +/- 0.2 microM. These findings pave the way to the design of new antimycobacterial drugs.
The FEBS Journal,2006,273,(20):4778–4789.
7,8-Diaminoperlargonic acid aminotransferase from Mycobacterium tuberculosis, a potential therapeutic target[Reference:
WebLink]
METHODS AND RESULTS:
Diaminopelargonic acid aminotransferase (DAPA AT), which is involved in biotin biosynthesis, catalyzes the transamination of 8-Amino-7-oxononanoic acid (KAPA) using S-adenosyl-l-methionine (AdoMet) as amino donor. Mycobacterium tuberculosis DAPA AT, a potential therapeutic target, has been overproduced in Escherichia coli and purified to homogeneity using a single efficient step on a nickel-affinity column.
CONCLUSIONS:
The enzyme shows an electronic absorption spectrum typical of pyridoxal 5′-phosphate-dependent enzymes and behaves as a homotetramer in solution.
