A carboxypeptidase inhibitor
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2-Guanidinoethylmercaptosuccinic Acid

Item No. 19354

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-[[2-[(aminoiminomethyl)amino]ethyl]thio]-butanedioic acid
CAS Number
77482-44-1
Synonyms
  • GEMSA
Molecular Formula
C7H13N3O4S
Formula Weight
235.3
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Water: Soluble
SMILES
OC(C(CC(O)=O)SCCNC(N)=N)=O
InChi Code
InChI=1S/C7H13N3O4S/c8-7(9)10-1-2-15-4(6(13)14)3-5(11)12/h4H,1-3H2,(H,11,12)(H,13,14)(H4,8,9,10)
InChi Key
VKVCLXDFOQQABP-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $202

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    Product Description

    2-Guanidinoethylmercaptosuccinic acid (GEMSA) is a potent inhibitor of enkephalin convertase (Ki = 8.8 nM) that is functional in vivo.1,2 It is a peptidomimetic inhibitor, occupying the specificity pocket of the enzyme.3 GEMSA can also inhibit other carboxypeptidases, including thrombin-activatable fibrinolysis inhibitor.4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Przewlocka, B., Dziedzicka, M., Silberring, J., et al. Analgesic and convulsant effects of guanidinoethylmercaptosuccinic acid (GEMSA)--a potent enkephalin convertase inhibitor. Neuropeptides 8(4), 359-365 (1986).

    2. Bommer, M., Nikolarakis, K., Noble, E.P., et al. In vivo modulation of rat hypothalamic opioid peptide content by intracerebroventricular injection of guanidinoethylmercaptosuccinic acid (GEMSA): Possible physiological role of enkephalin convertase. Brain Res. 492(1-2), 305-313 (1989).

    3. Aloy, P., Companys, V., Vendrell, J., et al. The crystal structure of the inhibitor-complexed carboxypeptidase D domain II and the modeling of regulatory carboxypeptidases. The Journal of Biological Chemisty 276(19), 16177-16184 (2001).

    4. Bajzar, L., Manuel, R., and Nesheim, M.E. Purification and characterization of TAFI, a thrombin-activable fibrinolysis inhibitor. The Journal of Biological Chemisty 270(24), 14477-14484 (1995).

    5. Ore, F.D., Ajandouz, E.H., Giardina, T., et al. The membrane-bound basic carboxypeptidase from hog intestinal mucosa. Biochim. Biophys. Acta 1421(2), 234-248 (2016).