S-Adenosylmethioninamine
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| Names | |
|---|---|
| IUPAC name
S-(3-Aminopropyl)-S-methyl-5′-thioadenosin-5′-ium | |
| Systematic IUPAC name
(3-Aminopropyl){[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}methylsulfanium | |
| Other names
S-Adenosyl-(5′)-3-methylthiopropylamine decarboxylated S-adenosyl methionine decarboxy-S-adenosyl methionine (5-Deoxy-5-adenosyl)(3-aminopropyl)methylsulfonium cation | |
| Identifiers | |
3D model (JSmol) |
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| Abbreviations | dAdoMet, dc-SAM |
| ChEBI | |
| ChemSpider | |
| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C14H23N6O3S+ | |
| Molar mass | 355.43582 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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S-Adenosylmethioninamine is a substrate that is required for the biosynthesis of polyamines including spermidine, spermine, and thermospermine.[1] It is produced by decarboxylation of S-adenosyl methionine.
This reaction is catalyzed by S-adenosylmethionine decarboxylase.[2] The enzyme binds to S-adenosylmethionine (SAM) and removes the carboxyl group from the methionine. Once formed, S-adenosylmethioninamine donates its aminopropyl group to synthesize polyamines.[3] Polyamines are important for DNA stability, RNA function, and cell growth.[4]
S-Adenosylmethioninamine is used for regulating metabolic pathways. It is important for the synthesis of metabolites and cofactors, and for the absorption and digestion of proteins.[5] In addition, S-adenosylmethioninamine can be used as a biomarker in metabolic pathways. This is important because it helps in early detection of various cancers and can help minimize metabolic disorders.[6] For instance, recent data shows that in low concentrations of methionine, S-adenosylmethioninamine is unable to produce the polyamines, spermine and spermidine.[7] S-Adenosylmethioninamine can be utilized in cancer research and further testing can be done to better understand its mechanism and its role in the body.
See also
[edit]References
[edit]- ↑ Takahashi, Taku; Kakehi, Jun-Ichi (2009-10-13). "Polyamines: Ubiquitous polycations with unique roles in growth and stress responses". Annals of Botany. 105 (1): 1–6. doi:10.1093/aob/mcp259. PMC 2794062. PMID 19828463.
- ↑ Campbell, Mary K.; Farrell, Shawn O.; McDougal, Owen M. (2016). Biochemistry (9th ed.). Boston, MA: Cengage Learning. ISBN 978-1-305-96113-5.
- ↑ Sirasunthorn, Nichanun; Jailwala, Anuj; Gerber, Anna; Comstock, Lindsay R. (2019-09-18). "Evaluation of N-Mustard Analogues of S-Adenosyl-L-methionine with Eukaryotic DNA Methyltransferase 1". ChemistrySelect. 4 (35): 10525–10531. doi:10.1002/slct.201902940. ISSN 2365-6549.
- ↑ Takahashi, Taku; Kakehi, Jun-Ichi (2009-10-13). "Polyamines: Ubiquitous polycations with unique roles in growth and stress responses". Annals of Botany. 105 (1): 1–6. doi:10.1093/aob/mcp259. PMC 2794062. PMID 19828463.
- ↑ Hu, Zhigang; Liu, Xiaolin (2023-03-08). "Integration of Transcriptomics and Non-Targeted Metabolomics Reveals the Underlying Mechanism of Skeletal Muscle Development in Duck during Embryonic Stage". International Journal of Molecular Sciences. 24 (6): 5214. doi:10.3390/ijms24065214. ISSN 1422-0067. PMC 10049352. PMID 36982289.
- ↑ Choi, Seong Ji; Choi, Hyuk Soon; Kim, Hyunil; Lee, Jae Min; Kim, Seung Han; Yoon, Jai Hoon; Keum, Bora; Kim, Hyo Jung; Chun, Hoon Jai; Park, Youngja H. (2024-09-01). "Gastric Cancer and Intestinal Metaplasia: Differential Metabolic Landscapes and New Pathways to Diagnosis". International Journal of Molecular Sciences. 25 (17): 9509. doi:10.3390/ijms25179509. ISSN 1422-0067. PMC 11395121. PMID 39273456.
- ↑ Massaro, Chelsea; Thomas, Jenna; Ikhlef, Houssine; Dinara, Sharifa; Cronk, Sara; Moots, Holly; Phanstiel, Otto (2020-03-26). "Serendipitous Discovery of Leucine and Methionine Depletion Agents during the Search for Polyamine Transport Inhibitors". Journal of Medicinal Chemistry. 63 (6): 2814–2832. doi:10.1021/acs.jmedchem.9b00568. ISSN 1520-4804. PMID 32069402.