Leu-Leu-Leu - ≥98% , CAS No.10329-75-6

CAS: 10329-75-6 Cat. No.: L121357 Molecular Weight: 357.49

GRADE & PURITY ≥98%

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- | AKOS027320356 | UNII-L6HEL5ZI2V | L6HEL5ZI2V | L-Leucine, N-

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

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.

Specifications

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- | AKOS027320356 | UNII-L6HEL5ZI2V | L6HEL5ZI2V | L-Leucine, N-

Specifications & Purity

≥98%

Storage

Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%

Names and Identifiers

• Canonical Smiles: CC(C)CC(C(=O)NC(CC(C)C)C(=O)NC(CC(C)C)C(=O)O)N
• IUPAC Name: (2S)-2-[[(2S)-2-[[(2S)-2-amino-4-methylpentanoyl]amino]-4-methylpentanoyl]amino]-4-methylpentanoic acid
• InChIKey: DNDWZFHLZVYOGF-KKUMJFAQSA-N
• 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
• 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
• Molecular Weight: 357.49
• Reaxy-Rn: 1729803
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1729803&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Not available
• Direct Parent: Peptides
• Alternative Parents: Leucine and derivatives N-acyl-alpha amino acids Methyl-branched fatty acids Amino acids Propargyl-type 1,3-dipolar organic compounds Monocarboxylic acids and derivatives Carboxylic acids Carboximidic acids Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Alpha peptide - Leucine or derivatives - N-acyl-alpha-amino acid - N-acyl-alpha amino acid or derivatives - Alpha-amino acid or derivatives - Branched fatty acid - Methyl-branched fatty acid - Fatty acyl - Fatty acid - Amino acid or derivatives - Amino acid - Carboximidic acid - Carboximidic acid derivative - Carboxylic acid - Monocarboxylic acid or derivatives - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Organic oxide - Organic oxygen compound - Primary aliphatic amine - Amine - Organic nitrogen compound - Hydrocarbon derivative - Organonitrogen compound - Organooxygen compound - Organopnictogen compound - Primary amine - Carbonyl group - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
• External Descriptors: tripeptide

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 357.500 g/mol
• XLogP3: -0.900
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 11
• Exact Mass: 357.263 Da
• Monoisotopic Mass: 357.263 Da
• Topological Polar Surface Area: 122.000 Ų
• Heavy Atom Count: 25
• Formal Charge: 0
• Complexity: 450.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 3
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

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,      [PMID:37793042] [10.1021/acs.jafc.3c04033]

2. Jiying Zhu, Wei Jia, Jian Peng.  (2024)  Dissecting the binding effect of Crocetin glucosyltransferase 2 in crocetin biotransformation in saffron (Crocus sativus L.) from different origins.  FOOD CHEMISTRY,      [PMID:38838622] [10.1016/j.foodchem.2024.139917]