An internal standard for the quantification of 5’-deoxy-5’-methylthioadenosine
Related Products
Unlabeled Version(s)
155935'-Deoxy-5'-methylthioadenosine
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5'-Deoxy-5'-methylthioadenosine-d3

Item No. 27836

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
7-[5-S-(methyl-d3)-5-thio-β-D-ribofuranosyl]-7H-purin-6-amine
CAS Number
174838-38-1
Synonyms
  • 5'-S-Methylthioadenosine-d3
  • MTA-d3
  • Vitamin L2-d3
Molecular Formula
C11H12D3N5O3S
Formula Weight
300.3
Purity
≥99% deuterated forms (d1-d3)
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMF: solubleDMSO: slightly solubleMethanol: slightly soluble
SMILES
O[C@H]1[C@H](N2C=NC3=C2N=CN=C3N)O[C@H](CSC([2H])([2H])[2H])[C@H]1O
InChi Code
InChI=1S/C11H15N5O3S/c1-20-2-5-7(17)8(18)11(19-5)16-4-15-6-9(12)13-3-14-10(6)16/h3-5,7-8,11,17-18H,2H2,1H3,(H2,12,13,14)/t5-,7-,8-,11-/m1/s1/i1D3
InChi Key
WUUGFSXJNOTRMR-YZLHILBGSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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.

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    1 mg

    $63

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    5 mg

    $289

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    Product Description

    5'-Deoxy-5'-methylthioadenosine-d3 (MTA-d3) is intended for use as an internal standard for the quantification of MTA (Item No. 15593) by GC- or LC-MS. MTA is an intermediate in the generation of adenine and methionine that is produced by the decarboxylation of S-adenosylmethionine.1 This nucleoside is a potent agonist of adenosine receptors (Kis = 0.15, 1.13, 13.9, and 0.68 μM for A1, A2A, A2B, and A3, respectively).2 At higher concentrations, MTA inhibits several enzymes, including protein carboxylmethyltransferase (Ki = 41 μM), S-adenosylhomocysteine hydrolase, SET methyltransferases, and spermidine and spermine synthases.3,1,4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Huang, S. Histone methyltransferases, diet nutrients and tumour suppressors. Nat. Rev. Cancer 2(6), 469-476 (2002).

    2. Kehraus, S., Gorzalka, S., Hallmen, C., et al. Novel amino acid derived natural products from the ascidian Atriolum robustum: Identification and pharmacological characterization of a unique adenosine derivative. J. Med. Chem. 47(9), 2243-2255 (2004).

    3. Oliva, A., Galletti, P., Zappia, V., et al. Studies on substrate specificity of S-adenosylmethionine: Protein-carboxyl methyltransferase from calf brain. Eur. J. Biochem. 104(2), 595-602 (1980).

    4. Cole, P.A. Chemical probes for histone-modifying enzymes. Nat. Chem. Biol. 4(10), 590-597 (2008).

    5. Lee, S.H., and Cho, Y.D. Induction of apoptosis in leukemia U937 cells by 5'-deoxy-5'-methylthioadenosine, a potent inhibitor of protein carboxylmethyltransferase. Exp. Cell Res. 240(2), 282-292 (1998).