Synonym
Trimethionine; Met-met-met;
IUPAC/Chemical Name
L-methionyl-L-methionyl-L-methionine
InChi Key
VWWGEKCAPBMIFE-SRVKXCTJSA-N
InChi Code
InChI=1S/C15H29N3O4S3/c1-23-7-4-10(16)13(19)17-11(5-8-24-2)14(20)18-12(15(21)22)6-9-25-3/h10-12H,4-9,16H2,1-3H3,(H,17,19)(H,18,20)(H,21,22)/t10-,11-,12-/m0/s1
SMILES Code
CSCC[C@@H](C(O)=O)NC([C@H](CCSC)NC([C@H](CCSC)N)=O)=O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
Preparing Stock Solutions
The following data is based on the
product
molecular weight
411.59
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Parker DD, Naider F, Becker JM. Separation of peptide transport and hydrolysis in trimethionine uptake by Saccharomyces cerevisiae. J Bacteriol. 1980 Aug;143(2):1066-9. PubMed PMID: 7009548; PubMed Central PMCID: PMC294421.
2: Barak Z, Gilbarg C. Specialized peptide transport system in Escherichia coli. J Bacteriol. 1975 Jun;122(3):1200-7. PubMed PMID: 1097394; PubMed Central PMCID: PMC246177.
3: Bekcer JM, Naider F. Peptide transport in yeast: uptake of radioactive trimethionine in Saccharomyces cerevisiae. Arch Biochem Biophys. 1977 Jan 15;178(1):245-55. PubMed PMID: 13720.
4: Logan DA, Becker JM, Naider F. Peptide transport in Candida albicans. J Gen Microbiol. 1979 Sep;114(1):179-86. PubMed PMID: 392049.
5: Becker JM, Dunsmore KP, Steinfeld AS, Naider F. Photoinactivation of peptide transport in Saccharomyces cerevisiae. Biochemistry. 1982 Nov 9;21(23):5967-71. PubMed PMID: 6758840.
6: Sarthou P, Gonneau M, Le Goffic F. Photoaffinity inhibition of peptide transport in yeast. Biochem Biophys Res Commun. 1983 Feb 10;110(3):884-9. PubMed PMID: 6340670.
7: Becker JM, Naider F. Stereospecificity of tripeptide utilization in a methionine auxotroph of Escherichia coli K-12. J Bacteriol. 1974 Oct;120(1):191-6. PubMed PMID: 4608021; PubMed Central PMCID: PMC245749.
8: Khare RK, Becker JM, Naider FR. Synthesis and anticandidal properties of polyoxin L analogues containing alpha-amino fatty acids. J Med Chem. 1988 Mar;31(3):650-6. PubMed PMID: 3279209.
9: Gajewski E, Dizdaroglu M, Krutzsch HC, Simic MG. OH radical-induced crosslinks of methionine peptides. Int J Radiat Biol Relat Stud Phys Chem Med. 1984 Jul;46(1):47-55. PubMed PMID: 6611320.
10: Naider F, Becker JM. Multiplicity of oligopeptide transport systems in Escherichia coli. J Bacteriol. 1975 Jun;122(3):1208-15. PubMed PMID: 1097395; PubMed Central PMCID: PMC246178.
11: Smith HA, Shenbagamurthi P, Naider F, Kundu B, Becker JM. Hydrophobic polyoxins are resistant to intracellular degradation in Candida albicans. Antimicrob Agents Chemother. 1986 Jan;29(1):33-9. PubMed PMID: 3524423; PubMed Central PMCID: PMC180359.
12: Hessler HJ, Pufahl C, Christophers E. Decreased releasability of basophils from patients with cold urticaria after cold exposure. Int Arch Allergy Appl Immunol. 1989;89(2-3):236-41. PubMed PMID: 2474511.
13: Ti JS, Steinfeld AS, Naider F, Gulumoglu A, Lewis SV, Becker JM. Anticandidal activity of pyrimidine-peptide conjugates. J Med Chem. 1980 Aug;23(8):913-8. PubMed PMID: 6995613.
