8-Amino-7-oxononanoic acid | CAS:4707-58-8

8-Amino-7-oxononanoic acid

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Description:

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.

In vitro:

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.

8-Amino-7-oxononanoic acid Description

Source:	From Penicillium chrysogenum
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Storage:	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. Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com
After receiving:	The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.

Structure Identification:

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.

Product Name	8-Amino-7-oxononanoic acid
Price:
CAS No.:	4707-58-8
Catalog No.:	CFN00051
Molecular Formula:	C₉H₁₇NO₃
Molecular Weight:	187.24 g/mol
Purity:	>=98%
Type of Compound:	Alkaloids
Physical Desc.:	Powder
Source:	From Penicillium chrysogenum
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Download:	COA MSDS SDF
Similar structural:	Comparison (Web) (SDF)
Guestbook:

Size /Price /Stock	10 mM * 100 uL in DMSO / Inquiry / In-stock 10 mM * 1 mL in DMSO / Inquiry / In-stock
Related Libraries	Precursors Compound Library Alkaloids Compound Library

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	5.3407 mL	26.7037 mL	53.4074 mL	106.8148 mL	133.5185 mL
5 mM	1.0681 mL	5.3407 mL	10.6815 mL	21.363 mL	26.7037 mL
10 mM	0.5341 mL	2.6704 mL	5.3407 mL	10.6815 mL	13.3518 mL
50 mM	0.1068 mL	0.5341 mL	1.0681 mL	2.1363 mL	2.6704 mL
100 mM	0.0534 mL	0.267 mL	0.5341 mL	1.0681 mL	1.3352 mL

CFN00013	Nitrosostromelin	182064-61-5	320.43	C₁₅H₃₂N₂O₅
CFN00017	2-Amino-3-dodecanol	N/A	201.35	C₁₂H₂₇NO
CFN00018	Halaminol B	389125-59-1	199.34	C₁₂H₂₅NO
CFN00035	(2S,3R,4E)-2-Amino-4-heptadecene-1,3-diol	6918-48-5	285.47	C₁₇H₃₅NO₂
CFN00036	Obscuraminol B	350485-82-4	253.43	C₁₆H₃₁NO
CFN00042	Streptenol E	N/A	227.30	C₁₂H₂₁NO₃
CFN00051	8-Amino-7-oxononanoic acid	4707-58-8	187.24	C₉H₁₇NO₃
CFN00063	Halaminol A	389125-56-8	227.39	C₁₄H₂₉NO