Specifications
- Purity
- ≥95% (NMR)
- Appearance
- White top off-white powder
- Identity
- 1H-NMR
Properties
- Solvents
- Soluble in water (20mg/ml) or DMSO (20mg/ml).
Available from stock
S-Adenosylmethionine
- SKU
- A0247
Category: Metabolites
- Synonyms
- SAM, SAMe, AdoMet, Ademethionine, S-Adenosyl-L-Methionine
- 29908-03-0
- CAS-Number
- C15H22N6O5S
- Molecular Formula
- 398.44
- Molecular Weight
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
- Shipping
- AMBIENT
- Short Term Storage
- -20°C
- Long Term Storage
- -20°C
- Handling Advice
- Protect from light and moisture.
- Use / Stability
- Stable for at least 2 years after receipt when stored at -20°C.
- Transportation
- Not dangerous goods
- Description
- S-Adenosylmethionine (SAM) is the first product of the “methionine cycle” and is implicated in the synthesis of polyamines and in the transsulfuration pathway leading to homocysteine and reduced glutathione (GSH) biosynthesis. SAM is synthesized from methionine and ATP in a reaction catalyzed by methionine adenosyltransferases (MATs). These enzymes are encoded by two genes, MAT1A and MAT2A. SAM plays an essential role as methyl-donor for the methylation reactions during which it is transformed to S-adenosylhomocysteine (SAH). SAH, a strong inhibitor of transmethylations, is transformed to homocysteine (HCY) by a specific hydroxylase. The methionine cycle plays a fundamental role in the cellular metabolism and the alteration of its functionality causes important disorders linked to modification of DNA methylation and gene expression, redox imbalance and metabolic reprogramming in liver and brain. More than 40 methyl transfers from SAM are known, to various substrates such as nucleic acids, proteins, lipids and secondary metabolites. In bacteria, SAM is bound by the SAM riboswitch, which regulates genes involved in methionine or cysteine biosynthesis. In eukaryotic cells, SAM serves as a regulator of a variety of processes including DNA, tRNA, and rRNA methylation
- Smiles
- C[S+](C[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C=NC3=C(N)N=CN=C32)O1)CC[C@H](N)C([O-])=O
- InChi Key
- MEFKEPWMEQBLKI-AIRLBKTGSA-N
- References
- [1] S.C. Lu, et al., Physiol. Rev. 92, 1515 (2012) , [2] R.M. Pascale, et al., Cells 11, 409 (2022)
- InChi
- InChI=1S/C15H22N6O5S/c1-27(3-2-7(16)15(24)25)4-8-10(22)11(23)14(26-8)21-6-20-9-12(17)18-5-19-13(9)21/h5-8,10-11,14,22-23H,2-4,16H2,1H3,(H2-,17,18,19,24,25)/t7-,8+,10+,11+,14+,27?/m0/s1
S-Adenosylmethionine (SAM) is the first product of the “methionine cycle” and is implicated in the synthesis of polyamines and in the transsulfuration pathway leading to homocysteine and reduced glutathione (GSH) biosynthesis. SAM is synthesized from methionine and ATP in a reaction catalyzed by methionine adenosyltransferases (MATs). These enzymes are encoded by two genes, MAT1A and MAT2A. SAM plays an essential role as methyl-donor for the methylation reactions during which it is transformed to S-adenosylhomocysteine (SAH). SAH, a strong inhibitor of transmethylations, is transformed to homocysteine (HCY) by a specific hydroxylase. The methionine cycle plays a fundamental role in the cellular metabolism and the alteration of its functionality causes important disorders linked to modification of DNA methylation and gene expression, redox imbalance and metabolic reprogramming in liver and brain. More than 40 methyl transfers from SAM are known, to various substrates such as nucleic acids, proteins, lipids and secondary metabolites. In bacteria, SAM is bound by the SAM riboswitch, which regulates genes involved in methionine or cysteine biosynthesis. In eukaryotic cells, SAM serves as a regulator of a variety of processes including DNA, tRNA, and rRNA methylation
Additional information
| Synonyms | SAM, SAMe, AdoMet, Ademethionine, S-Adenosyl-L-Methionine |
|---|---|
| Purity | ≥95% (NMR) |
| Appearance | White top off-white powder |
| CAS-Number | 29908-03-0 |
| Molecular Formula | C15H22N6O5S |
| Molecular Weight | 398.44 |
| Identity | 1H-NMR |
| Solvents | Soluble in water (20mg/ml) or DMSO (20mg/ml). |
| Smiles | C[S+](C[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C=NC3=C(N)N=CN=C32)O1)CC[C@H](N)C([O-])=O |
| InChi Key | MEFKEPWMEQBLKI-AIRLBKTGSA-N |
| Shipping | AMBIENT |
| Short Term Storage | -20°C |
| Long Term Storage | -20°C |
| Handling Advice | Protect from light and moisture. |
| Use / Stability | Stable for at least 2 years after receipt when stored at -20°C. |
| Transportation | Not dangerous goods |
| References | [1] S.C. Lu, et al., Physiol. Rev. 92, 1515 (2012), [2] R.M. Pascale, et al., Cells 11, 409 (2022) |
| InChi | InChI=1S/C15H22N6O5S/c1-27(3-2-7(16)15(24)25)4-8-10(22)11(23)14(26-8)21-6-20-9-12(17)18-5-19-13(9)21/h5-8,10-11,14,22-23H,2-4,16H2,1H3,(H2-,17,18,19,24,25)/t7-,8+,10+,11+,14+,27?/m0/s1 |
| Quantity | 50 mg, 100 mg, Bulk |
