A racemic mixture of 8(R)-KAPA and 8(S)-KAPA
Technical Support & Resources

Information provided in the product description is from published literature. Due to the nature of scientific experimentation, your results (e.g., selectivity and effective concentrations) or specific application for this product may differ. If you have questions about how this product fits your application, please contact our technical support staff.

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

(±)8-Amino-7-Oxononanoic Acid (hydrochloride)

Item No. 40973

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
8-amino-7-oxo-nonanoic acid, monohydrochloride
CAS Number
21286-96-4
Synonyms
  • (±)8-KAPA
Molecular Formula
C9H17NO3 • HCl
Formula Weight
223.7
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Sparingly soluble: 1-10 mg/mlEthanol: Slightly soluble: 0.1-1 mg/mlPBS (pH 7.2): Sparingly soluble: 1-10 mg/ml
SMILES
NC(C)C(CCCCCC(O)=O)=O.Cl
InChi Code
InChI=1S/C9H17NO3.ClH/c1-7(10)8(11)5-3-2-4-6-9(12)13;/h7H,2-6,10H2,1H3,(H,12,13);1H
InChi Key
ZGPOLJARQCHVLY-UHFFFAOYSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Recommended Products

Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    1 mg

    $28

    Add

    5 mg

    $104

    Add

    10 mg

    $193

    Add

    50 mg

    $413

    Add
    Product Description

    (±)8-Amino-7-Oxononanoic acid ((±)8-KAPA) is a racemic mixture of 8(R)-KAPA and the vitamer of biotin 8(S)-KAPA.1,2 It is biosynthesized as the 8(S) form but racemizes in culture media in a pH-dependent manner, with a higher racemization rate under very low (pH <2), physiological, and basic pH conditions.2 8(S)-KAPA increases proliferation in S. cerevisiae in a concentration-dependent manner and is an intermediate in the biosynthesis of biotin (Item No. 22582) in microbes. 8(S)-KAPA, but not 8(R)-KAPA, is a substrate for E. coli and M. tuberculosis 7,8-diaminopelargonic acid aminotransferase (DAPA AT), which leads to accumulation of 8(R)-KAPA in M. tuberculosis cultures after exogenous application of racemic KAPA.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lucet, D., Le Gall, T., Mioskowski, C., et al. First synthesis of both enantiomers of the biotin vitamer 8-amino-7-oxopelargonic acid. Tetrahedron-Asymmetr. 7(4), 985-988 (1996).

    2. Mann, S., Colliandre, L., Labesse, G., et al. Inhibition of 7,8-diaminopelargonic acid aminotransferase from Mycobacterium tuberculosis by chiral and achiral anologs of its substrate: biological implications. Biochimie 91(7), 826-834 (2009).