MedKoo Cat#: 597456 | Name: Leucyl-leucyl-leucine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Leucyl-leucyl-leucine is an endosome escape moiety, may be used for pH-dependent endosomal membrane disruption to release agents such as antisense oligonucleotides (AONs) inside cells. Trileucine is used to evaluate the absorption characteristics of reversed phase liquid chromatography (HPLC) media.

Chemical Structure

Leucyl-leucyl-leucine
CAS#10329-75-6

Theoretical Analysis

MedKoo Cat#: 597456

Name: Leucyl-leucyl-leucine

CAS#: 10329-75-6

Chemical Formula: C18H35N3O4

Exact Mass: 357.2628

Molecular Weight: 357.49

Elemental Analysis: C, 60.48; H, 9.87; N, 11.75; O, 17.90

Price and Availability

Size Price Availability Quantity
500mg USD 340.00
1g USD 550.00
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Related CAS #
No Data
Synonym
Leucyl-leucyl-leucine; Trileucine;
IUPAC/Chemical Name
L-leucyl-L-leucyl-L-leucine
InChi Key
DNDWZFHLZVYOGF-KKUMJFAQSA-N
InChi Code
InChI=1S/C18H35N3O4/c1-10(2)7-13(19)16(22)20-14(8-11(3)4)17(23)21-15(18(24)25)9-12(5)6/h10-15H,7-9,19H2,1-6H3,(H,20,22)(H,21,23)(H,24,25)/t13-,14-,15-/m0/s1
SMILES Code
CC(C)C[C@@H](C(O)=O)NC([C@H](CC(C)C)NC([C@H](CC(C)C)N)=O)=O
Appearance
Solid powder
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 357.49 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.

Recalculate based on batch purity %
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: Go K, Parthasarathy R. Crystal structure and a twisted beta-sheet conformation of the tripeptide L-leucyl-L-leucyl-L-leucine monohydrate trimethanol solvate: conformation analysis of tripeptides. Biopolymers. 1995 Nov;36(5):607-14. PubMed PMID: 7578952. 2: Strauch KL, Carter TH, Miller CG. Overproduction of Salmonella typhimurium peptidase T. J Bacteriol. 1983 Nov;156(2):743-51. PubMed PMID: 6313618; PubMed Central PMCID: PMC217891. 3: Felsenberg J, Dyck Y, Kloß A, Dahlmann B, Kloetzel PM, Eisenhardt D. Two inhibitors of the ubiquitin proteasome system enhance long-term memory formation upon olfactory conditioning in the honeybee (Apis mellifera). J Exp Biol. 2014 Oct 1;217(Pt 19):3441-6. doi: 10.1242/jeb.108142. Epub 2014 Jul 25. PubMed PMID: 25063852. 4: Ding H, Portilla-Arias J, Patil R, Black KL, Ljubimova JY, Holler E. Distinct mechanisms of membrane permeation induced by two polymalic acid copolymers. Biomaterials. 2013 Jan;34(1):217-25. doi: 10.1016/j.biomaterials.2012.08.016. Epub 2012 Oct 9. PubMed PMID: 23063368; PubMed Central PMCID: PMC3487713. 5: Bosman BW, Tan PS, Konings WN. Purification and Characterization of a Tripeptidase from Lactococcus lactis subsp. cremoris Wg2. Appl Environ Microbiol. 1990 Jun;56(6):1839-43. PubMed PMID: 16348224; PubMed Central PMCID: PMC184519. 6: Adibi SA, Johns BA. Utilization of intravenously infused tripeptides in baboons: effect on plasma concentration and urinary excretion of amino acids. Metabolism. 1983 Feb;32(2):103-5. PubMed PMID: 6827980. 7: Andrzejewska A, Gritti F, Guiochon G. Investigation of the adsorption mechanism of a peptide in reversed phase liquid chromatography, from pH controlled and uncontrolled solutions. J Chromatogr A. 2009 May 1;1216(18):3992-4004. doi: 10.1016/j.chroma.2009.03.014. Epub 2009 Mar 13. PubMed PMID: 19328489. 8: Nakamura K, Fujita Y, Itoh Y, Yamane K. Modification of length, hydrophobic properties and electric charge of Bacillus subtilis alpha-amylase signal peptide and their different effects on the production of secretory proteins in B. subtilis and Escherichia coli cells. Mol Gen Genet. 1989 Mar;216(1):1-9. PubMed PMID: 2471921. 9: Kabashima T, Yu Z, Tang C, Nakagawa Y, Okumura K, Shibata T, Lu J, Kai M. A selective fluorescence reaction for peptides and chromatographic analysis. Peptides. 2008 Mar;29(3):356-63. doi: 10.1016/j.peptides.2007.11.014. Epub 2007 Nov 29. PubMed PMID: 18179843. 10: Kawakami K, Takeshita F, Puri RK. Identification of distinct roles for a dileucine and a tyrosine internalization motif in the interleukin (IL)-13 binding component IL-13 receptor alpha 2 chain. J Biol Chem. 2001 Jul 6;276(27):25114-20. Epub 2001 May 14. PubMed PMID: 11352909. 11: Kolstad J, Law BA. Comparative peptide specificity of cell wall, membrane and intracellular peptidases of group N streptococci. J Appl Bacteriol. 1985 May;58(5):449-55. PubMed PMID: 3924874. 12: Steverding D, Spackman RW, Royle HJ, Glenn RJ. Trypanocidal activities of trileucine methyl vinyl sulfone proteasome inhibitors. Parasitol Res. 2005 Jan;95(1):73-6. Epub 2004 Dec 1. PubMed PMID: 15578221. 13: Conconi M, Petropoulos I, Emod I, Turlin E, Biville F, Friguet B. Protection from oxidative inactivation of the 20S proteasome by heat-shock protein 90. Biochem J. 1998 Jul 15;333 ( Pt 2):407-15. PubMed PMID: 9657982; PubMed Central PMCID: PMC1219599. 14: Lechuga-Ballesteros D, Charan C, Stults CL, Stevenson CL, Miller DP, Vehring R, Tep V, Kuo MC. Trileucine improves aerosol performance and stability of spray-dried powders for inhalation. J Pharm Sci. 2008 Jan;97(1):287-302. PubMed PMID: 17823950. 15: Yamasaki S, Kawakami A, Nakashima T, Nakamura H, Kamachi M, Honda S, Hirai Y, Hida A, Ida H, Migita K, Kawabe Y, Koji T, Furuichi I, Aoyagi T, Eguchi K. Importance of NF-kappaB in rheumatoid synovial tissues: in situ NF-kappaB expression and in vitro study using cultured synovial cells. Ann Rheum Dis. 2001 Jul;60(7):678-84. PubMed PMID: 11406522; PubMed Central PMCID: PMC1753739. 16: Ullah I, Chung K, Beloor J, Kim J, Cho M, Kim N, Lee KY, Kumar P, Lee SK. Trileucine residues in a ligand-CPP-based siRNA delivery platform improve endosomal escape of siRNA. J Drug Target. 2017 Apr;25(4):320-329. doi: 10.1080/1061186X.2016.1258566. Epub 2016 Nov 22. PubMed PMID: 27820977.