| Field | Specification |
|---|---|
| Alternative names | Met-met-met |
| CAS no. | |
| Applications | |
| Molecular weight | |
| Molecular formula | C15H29N3O4S3 |
| SMILES | |
| Storage | |
| Shipping | |
| Catalog no. (Mfr.) | |
| Main SKU |
Compound Overview
Trimethionine, also known as Met-met-met, is an orally active tripeptide substrate of peptide transport systems. It interacts with the triple-leucine-triple-threonine transport system and the oligopeptide permease (Opp) system in Escherichia coli, competing for uptake and transport, and it antagonizes the toxicity of threonine tripeptide and ornithine tripeptide while competing with peptide-supported growth and amino-acid-source utilization in E. coli strains. It is taken up by Candida albicans through a carrier-mediated, energy-dependent process and is then hydrolyzed intracellularly to free methionine, and it can be used in studies of Candida albicans infections[3]. It has the molecular formula C15H29N3O4S3 and a molecular weight of 411.59 g/mol.
Physical & Chemical Properties
| CAS Number | 14486-15-8 |
|---|---|
| Molecular Formula | C15H29N3O4S3 |
| Molecular Weight | 411.59 g/mol |
| SMILES | [C@H](C(N[C@@H](CCSC)C(O)=O)=O)(NC([C@H](CCSC)N)=O)CCSC |
| Storage | Please store the product under the recommended conditions in the Certificate of Analysis. |
| Shipping | Room temperature in continental US; may vary elsewhere. |
Literature Cited
Sources cited in this description and in the In Vitro & In Vivo Data tab. Peer-reviewed publications that used this product are listed under References.
Safety
For Research Use Only. Not for use in diagnostic or therapeutic procedures, and not for human or veterinary use. Handle in accordance with your institution's chemical hygiene plan.
In Vitro
Trimethionine competes with trileucine for use in the Escherichia coli K-12 TD-V Opp+ and Opp- strains, indicating that the trileucine-threonine transport system can recognize it[1]. In Escherichia coli W M-26-26, Trimethionine can be transported through the general oligopeptide transport system (Opp), since it relieves triornithine toxicity by competitive uptake inhibition[1]. In Escherichia coli W M-26-26, Trimethionine competes with tetra-lysine for utilization, confirming it as a substrate for the general oligopeptide transport system (Opp)[1]. Candida albicans WD 18-4 takes up Trimethionine through a saturable, energy-dependent carrier-mediated system, and intracellular peptidases immediately and rapidly hydrolyze it to free methionine after uptake[3]. The Trimethionine transport system in Candida albicans WD 18-4 is highly specific and strongly recognizes tripeptides that have an N-terminal acetyl group, a D-type residue at the first position, or hydrophobic side chains[3].
In Vivo
In young male Wistar rats, an SPI-based diet delivering Trimethionine (diet feeding; daily; 14 days; 3.00% methionine level in nitrogen source) gives a significantly high protein efficiency ratio (3.21) and supports healthy growth across 14 days[2].
| Animal Model | Wistar (male, 4 weeks old)[2] |
|---|---|
| Dosage | 3.00% (methionine level in nitrogen source) |
| Administration | diet feeding; daily; 14 days |
| Result | Achieved a protein efficiency ratio (PER) of 3.21. Supported a growth rate comparable to that of rats fed diets supplemented with free methionine or dimethionine over the 14-day feeding period. |
Data provided by the manufacturer. Numbered citations refer to the Literature Cited list in the product description.
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