Synonym
Lysine ketoisocaproate
IUPAC/Chemical Name
L-Lysine mono(4-methyl-2-oxovalerate)
InChi Key
AZOLWFLKEMTKDO-JEDNCBNOSA-N
InChi Code
InChI=1S/C6H14N2O2.C6H10O3/c7-4-2-1-3-5(8)6(9)10;1-4(2)3-5(7)6(8)9/h5H,1-4,7-8H2,(H,9,10);4H,3H2,1-2H3,(H,8,9)/t5-;/m0./s1
SMILES Code
N[C@@H](CCCCN)C(O)=O.CC(C)CC(C(O)=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
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
276.33
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: Renguet E, Ginion A, Gélinas R, Bultot L, Auquier J, Robillard Frayne I, Daneault C, Vanoverschelde JL, Des Rosiers C, Hue L, Horman S, Beauloye C, Bertrand L. Metabolism and acetylation contribute to leucine-mediated inhibition of cardiac glucose uptake. Am J Physiol Heart Circ Physiol. 2017 Aug 1;313(2):H432-H445. doi: 10.1152/ajpheart.00738.2016. Epub 2017 Jun 23. PubMed PMID: 28646031.
2: Kaneko Y, Kimura Y, Kimura H, Niki I. L-cysteine inhibits insulin release from the pancreatic beta-cell: possible involvement of metabolic production of hydrogen sulfide, a novel gasotransmitter. Diabetes. 2006 May;55(5):1391-7. PubMed PMID: 16644696.
3: Humbert B, Bleis P, Martin L, Dumon H, Darmaun D, Nguyen P. Effects of dietary protein restriction and amino acids deficiency on protein metabolism in dogs. J Anim Physiol Anim Nutr (Berl). 2001 Aug;85(7-8):255-62. PubMed PMID: 11686798.
4: Nair KS, Schwartz RG, Welle S. Leucine as a regulator of whole body and skeletal muscle protein metabolism in humans. Am J Physiol. 1992 Nov;263(5 Pt 1):E928-34. PubMed PMID: 1443126.
5: Nair KS, Matthews DE, Welle SL, Braiman T. Effect of leucine on amino acid and glucose metabolism in humans. Metabolism. 1992 Jun;41(6):643-8. PubMed PMID: 1640850.
6: Rabkin R, Tsao T, Shi JD, Mortimore G. Amino acids regulate kidney cell protein breakdown. J Lab Clin Med. 1991 Jun;117(6):505-13. PubMed PMID: 1904473.
7: Blachier F, Leclercq-Meyer V, Marchand J, Woussen-Colle MC, Mathias PC, Sener A, Malaisse WJ. Stimulus-secretion coupling of arginine-induced insulin release. Functional response of islets to L-arginine and L-ornithine. Biochim Biophys Acta. 1989 Sep 19;1013(2):144-51. PubMed PMID: 2504287.
8: Funk MA, Lowry KR, Baker DH. Utilization of the L- and DL-isomers of alpha-keto-beta-methylvaleric acid by rats and comparative efficacy of the keto analogs of branched-chain amino acids provided as ornithine, lysine and histidine salts. J Nutr. 1987 Sep;117(9):1550-5. PubMed PMID: 3116181.
9: Henquin JC, Nenquin M, Awouters P, Cogneau M. Magnesium uptake by pancreatic islet cells is modulated by stimulators and inhibitors of the B-cell function. Eur J Biochem. 1986 Mar 17;155(3):653-7. PubMed PMID: 3514212.
10: Tribble D, Shapira R. Myelin proteins: degradation in rat brain initiated by metabolites causative of maple syrup urine disease. Biochem Biophys Res Commun. 1983 Jul 29;114(2):440-6. PubMed PMID: 6411085.
11: Tachiki T, Tochikura T. Further characterization of L-leucine-pyruvate transaminase from Acetobacter suboxydans. Biochim Biophys Acta. 1975 Aug 26;397(2):342-6. PubMed PMID: 1156585.
12: Stieglitz B, Calvo JM. Effect of 4-azaleucine upon leucine metabolism in Salmonella typhimurium. J Bacteriol. 1971 Oct;108(1):95-104. PubMed PMID: 4330744; PubMed Central PMCID: PMC247037.
