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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Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to
24 months(2-8C).
Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour.
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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.
