Leupeptin hemisulfate salt - Moligand™, ≥90%(HPLC) , CAS No.103476-89-7

CAS: 103476-89-7 Cat. No.: L111765 Molecular Weight: 475.59 EC Number: 600-443-5 PubChem CID: 2733491

GRADE & PURITY Moligand™, ≥90%(HPLC)

Synonyms

Acetyl-L-leucyl-L-leucyl-L-argininal hemisulfate | Acetyl-Leu-Leu-Arg-al

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Leupeptin, or N-acetyl-L-leucyl-L-leucyl-L-argininal, is a naturally occurring tripeptide that acts particularly as a serine protease inhibitor and as a cysteine protease inhibitor. Its mechanism of action involves structurally similar covalent binding reactions: In the active site of serine proteases, leupeptin forms a covalent hemiacetal adduct between the aldehyde group of leupeptin and the hydroxyl group of a serine residue in the enzyme active site. In the active site of cysteine proteases, the electrophilic (aldehyde) carbon of leupeptin forms a comparable bond with the sulfur atom of a cysteine residue in the enzyme active site.

Specifications

Synonyms

Acetyl-L-leucyl-L-leucyl-L-argininal hemisulfate | Acetyl-Leu-Leu-Arg-al

Specifications & Purity

Moligand™, ≥90%(HPLC)

Biochemical and Physiological Mechanisms

Reversible, competitive serine/cysteine protease inhibitor. Inhibits cathepsins B, H, L and S, calpain and trypsin. Orally active. Antioxidant and anti-inflammatory agent. Active in vivo and in vitro .

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

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

Grade

Moligand™

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one week. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Toxic, refer to SDS for further information. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥90%(HPLC)

Names and Identifiers

• Canonical Smiles: CC(C)CC(C(=O)NC(CC(C)C)C(=O)NC(CCCN=C(N)N)C=O)NC(=O)C.CC(C)CC(C(=O)NC(CC(C)C)C(=O)NC(CCCN=C(N)N)C=O)NC(=O)C.OS(=O)(=O)O
• IUPAC Name: (2S)-2-acetamido-N-[(2S)-1-[[(2S)-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]-4-methylpentanamide;sulfuric acid
• InChIKey: CIPMKIHUGVGQTG-VFFZMTJFSA-N
• INCHI: 1S/2C20H38N6O4.H2O4S/c2*1-12(2)9-16(24-14(5)28)19(30)26-17(10-13(3)4)18(29)25-15(11-27)7-6-8-23-20(21)22;1-5(2,3)4/h2*11-13,15-17H,6-10H2,1-5H3,(H,24,28)(H,25,29)(H,26,30)(H4,21,22,23);(H2,1,2,3,4)/t2*15-,16-,17-;/m00./s1
• Isomeric SMILES: CC(C)C[C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCN=C(N)N)C=O)NC(=O)C.CC(C)C[C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCN=C(N)N)C=O)NC(=O)C.OS(=O)(=O)O
• PubChem CID: 2733491
• Molecular Weight: 475.59

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Peptides
          • Level6 Dipeptides

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Peptides
• Direct Parent: Dipeptides
• Alternative Parents: Leucine and derivatives N-acyl-alpha amino acids and derivatives Alpha amino acid amides Organic sulfuric acids N-acyl amines Acetamides Secondary carboxylic acid amides Guanidines Propargyl-type 1,3-dipolar organic compounds Carboximidamides Organopnictogen compounds Organic oxides Hydrocarbon derivatives Aldehydes
• Molecular Framework: Not available
• Substituents: Alpha-dipeptide - Leucine or derivatives - N-acyl-alpha amino acid or derivatives - Alpha-amino acid amide - N-substituted-alpha-amino acid - Alpha-amino acid or derivatives - Sulfuric acid - Fatty amide - Fatty acyl - N-acyl-amine - Acetamide - Organic sulfuric acid or derivatives - Carboxamide group - Guanidine - Secondary carboxylic acid amide - Carboximidamide - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Aldehyde - Organonitrogen compound - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Carbonyl group - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
• External Descriptors: Not available

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

• Solubility: Soluble in water, ethanol, dimethyl formamide and acetic acid.
• Sensitivity: Moisture sensitive
• Molecular Weight: 951.200 g/mol
• Hydrogen Bond Donor Count: 12
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 28
• Exact Mass: 950.558 Da
• Monoisotopic Mass: 950.558 Da
• Topological Polar Surface Area: 421.000 Ų
• Heavy Atom Count: 65
• Formal Charge: 0
• Complexity: 683.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 6
• 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: 3

XLogP3

References

1. Jing Jin, Qiao‑Yun Hu, Wen‑Wen Xu, Wen‑Jia Zhu, Bei Liu, Jing Liu, Wei Wang, Hui‑Fang Zhou.  (2019)  Tanshinone IIA attenuates estradiol‑induced polycystic ovarian syndrome in mice by ameliorating FSHR expression in the ovary.  Experimental and Therapeutic Medicine,  17  (5): (3501-3508).  [PMID:30988730] [10.3892/etm.2019.7352]

2. Yunhua Zhang, Jinyun Ji, Xiao Zhao, Ruoheng Jin, Jianhong Li, Hu Wan.  (2017)  Expression, purification and enzymatic properties of a β-N-acetylhexosaminidase from brown planthopper, Nilaparvata lugens.  JOURNAL OF ASIA-PACIFIC ENTOMOLOGY,      [PMID:] [10.1016/j.aspen.2017.10.005]

3. Rongrong He, Ziwei Lv, Yinan Li, Shuchao Ren, Jiaqi Cao, Jun Zhu, Xinrong Zhang, Huimin Wu, Lihao Wan, Ji Tang, Shutong Xu, Xiao-Lin Chen, Zhipeng Zhou.  (2024)  tRNA-m1A methylation controls the infection of Magnaporthe oryzae by supporting ergosterol biosynthesis.  DEVELOPMENTAL CELL,      [PMID:39191251] [10.1016/j.devcel.2024.08.002]

4. Bangbang Li, Yanchen Wang, Pengzhao Chang, Hao Chen, Yangang Zhu, Nanxin Zhao, Zhimou Yang, Jingjing Li.  (2025)  In situ enzyme instructed peptide assembly favoring a three-target sequentially responsive fluorescence probe for the early identification of atherosclerotic plaque in vivo.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2025.167162]