Basic Description

Synonyms	CHEBI:74541 \| Trileucine \| l-leucyl-l-leucyl-l-leucine \| (S)-2-((S)-2-((S)-2-Amino-4-methylpentanamido)-4-methylpentanamido)-4-methylpentanoic acid \| Leu-leu-leu \| L-Leucine,L-leucyl-L-leucyl- \| CS-W011832 \| AKOS027320356 \| UNII-L6HEL5ZI2V \| L6HEL5ZI2V \|
Specifications & Purity	≥98%
Storage Temp	Store at -20°C,Argon charged
Shipped In	Ice chest + Ice pads
Product Description	Leu-Leu-Leu, 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.

Mechanisms of Action

Mechanism of Action	Action Type	target ID	Target Name	Target Type	Target Organism	Binding Site Name	References

Names and Identifiers

IUPAC Name	(2S)-2-[[(2S)-2-[[(2S)-2-amino-4-methylpentanoyl]amino]-4-methylpentanoyl]amino]-4-methylpentanoic acid
INCHI	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
InChi Key	DNDWZFHLZVYOGF-KKUMJFAQSA-N
Canonical SMILES	CC(C)CC(C(=O)NC(CC(C)C)C(=O)NC(CC(C)C)C(=O)O)N
Isomeric SMILES	CC(C)C[C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)O)N
WGK Germany	3
PubChem CID	82546
Molecular Weight	357.49

Certificates

Certificate of Analysis(COA)

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Lot Number	Certificate Type	Date	Item
I1525094	Certificate of Analysis	Jun 05, 2023	L121357

Safety and Hazards(GHS)

WGK Germany	3

Citations of This Product

How to Cite Aladdin Scientific Products?

1. Wei Jia, Jiying Zhu. (2023) Molecular Mechanism of ε-Polylysine Treatment of Animal-Derived Foods: Glycine Amidinotransferase Activity Implicates Upregulation of l-Arginine and Creatine. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 71 (41): (15106–15120). [PMID:37793042] [10.1021/acs.jafc.3c04033]

References

1. J Kolstad,B A Law. (1985-05-01) Comparative peptide specificity of cell wall, membrane and intracellular peptidases of group N streptococci.. The Journal of applied bacteriology, 58 ((5)): (449-455). [PMID:3924874]
2. K L Strauch,T H Carter,C G Miller. (1983-11-01) Overproduction of Salmonella typhimurium peptidase T.. Journal of bacteriology, 156 ((2)): (743-751). [PMID:6313618]
3. K Go,R Parthasarathy. (1995-11-01) 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, 36 ((5)): (607-614). [PMID:7578952]
4. M Conconi,I Petropoulos,I Emod,E Turlin,F Biville,B Friguet. (1998-07-11) Protection from oxidative inactivation of the 20S proteasome by heat-shock protein 90.. The Biochemical journal, 333 (( Pt 2)): (407-415). [PMID:9657982]
5. David Lechuga-Ballesteros,Chatan Charan,Cheryl L M Stults,Cynthia L Stevenson,Danforth P Miller,Reinhard Vehring,Vathana Tep,Mei-Chang Kuo. (2007-09-08) Trileucine improves aerosol performance and stability of spray-dried powders for inhalation.. Journal of pharmaceutical sciences, 97 ((1)): (287-302). [PMID:17823950]
6. Tsutomu Kabashima,Zhiqiang Yu,Chenhong Tang,Yoshiki Nakagawa,Kyosuke Okumura,Takayuki Shibata,Jianzhong Lu,Masaaki Kai. (2008-01-09) A selective fluorescence reaction for peptides and chromatographic analysis.. Peptides, 29 ((3)): (356-363). [PMID:18179843]
7. Anna Andrzejewska,Fabrice Gritti,Georges Guiochon. (2009-03-31) Investigation of the adsorption mechanism of a peptide in reversed phase liquid chromatography, from pH controlled and uncontrolled solutions.. Journal of chromatography. A, 1216 ((18)): (3992-4004). [PMID:19328489]
8. Hui Ding,Satoshi Inoue,Alexander V Ljubimov,Rameshwar Patil,Jose Portilla-Arias,Jinwei Hu,Bindu Konda,Kolja A Wawrowsky,Manabu Fujita,Natalya Karabalin,Takako Sasaki,Keith L Black,Eggehard Holler,Julia Y Ljubimova. (2010-10-06) Inhibition of brain tumor growth by intravenous poly (β-L-malic acid) nanobioconjugate with pH-dependent drug release [corrected].. Proceedings of the National Academy of Sciences of the United States of America, 107 ((42)): (18143-18148). [PMID:20921419]
9. Nicholas B Carrigy,Lu Liang,Hui Wang,Samuel Kariuki,Tobi E Nagel,Ian F Connerton,Reinhard Vehring. (2019-12-18) Trileucine and Pullulan Improve Anti-Campylobacter Bacteriophage Stability in Engineered Spray-Dried Microparticles.. Annals of biomedical engineering, 48 ((4)): (1169-1180). [PMID:31845128]
10. Gomez, et al.. (2021) Development of a formulation platform for a spray-dried, inhalable tuberculosis vaccine candidate.. International Journal of Pharmaceutics, 593 (120121-120121). [PMID:33278492]
11. S A Adibi,B A Johns. (1983-02-01) Utilization of intravenously infused tripeptides in baboons: effect on plasma concentration and urinary excretion of amino acids.. Metabolism: clinical and experimental, 32 ((2)): (103-105). [PMID:6827980]
12. K Kawakami,F Takeshita,R K Puri. (2001-05-16) 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.. The Journal of biological chemistry, 276 ((27)): (25114-25120). [PMID:11352909]
13. S Yamasaki,A Kawakami,T Nakashima,H Nakamura,M Kamachi,S Honda,Y Hirai,A Hida,H Ida,K Migita,Y Kawabe,T Koji,I Furuichi,T Aoyagi,K Eguchi. (2001-06-19) Importance of NF-kappaB in rheumatoid synovial tissues: in situ NF-kappaB expression and in vitro study using cultured synovial cells.. Annals of the rheumatic diseases, 60 ((7)): (678-684). [PMID:11406522]
14. Dietmar Steverding,Robert W Spackman,Howard J Royle,Robert J Glenn. (2004-12-04) Trypanocidal activities of trileucine methyl vinyl sulfone proteasome inhibitors.. Parasitology research, 95 ((1)): (73-76). [PMID:15578221]
15. Rameshwar Patil,José Portilla-Arias,Hui Ding,Satoshi Inoue,Bindu Konda,Jinwei Hu,Kolja A Wawrowsky,Paul K Shin,Keith L Black,Eggehard Holler,Julia Y Ljubimova. (2010-04-14) Temozolomide delivery to tumor cells by a multifunctional nano vehicle based on poly(β-L-malic acid).. Pharmaceutical research, 27 ((11)): (2317-2329). [PMID:20387095]
16. L Braiterman,L Nyasae,F Leves,A L Hubbard. (2011-04-02) Critical roles for the COOH terminus of the Cu-ATPase ATP7B in protein stability, trans-Golgi network retention, copper sensing, and retrograde trafficking.. American journal of physiology. Gastrointestinal and liver physiology, 301 ((1)): (G69-G81). [PMID:21454443]
17. Hui Ding,Jose Portilla-Arias,Rameshwar Patil,Keith L Black,Julia Y Ljubimova,Eggehard Holler. (2012-10-16) Distinct mechanisms of membrane permeation induced by two polymalic acid copolymers.. Biomaterials, 34 ((1)): (217-225). [PMID:23063368]
18. Mohammad Tanvir Sarwar,Yuko Ohara-Nemoto,Takeshi Kobayakawa,Mariko Naito,Takayuki K Nemoto. (2020-01-09) Characterization of substrate specificity and novel autoprocessing mechanism of dipeptidase A from Prevotella intermedia.. Biological chemistry, 401 ((5)): (629-642). [PMID:31913843]
19. Wei Jia, Jiying Zhu. (2023) Molecular Mechanism of ε-Polylysine Treatment of Animal-Derived Foods: Glycine Amidinotransferase Activity Implicates Upregulation of l-Arginine and Creatine. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 71 (41): (15106–15120). [PMID:37793042] [10.1021/acs.jafc.3c04033]

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SKU	Size	Availability	Price	Qty
L121357-250mg	250mg	Available within 4-8 weeks(?) Items will be manufactured post-order and can take 4-8 weeks. Thank you for your patience!	$88.90
L121357-1g	1g	Available within 4-8 weeks(?) Items will be manufactured post-order and can take 4-8 weeks. Thank you for your patience!	$272.90

Leu-Leu-Leu - 98%, high purity , CAS No.10329-75-6