54518-92-2

Basic information

• Product Name: L-LEUCINE CHLOROMETHYL KETONE HYDROCHLORIDE
• Synonyms: H-Leu-CMK.HClL-Leucine chloroMethyl ketone hydr;(S)-3-AMino-1-chloro-5-Methylhexan-2-one hydrochloride;2-Hexanone,3-aMino-1-chloro-5-Methyl-, hydrochloride, (3S)- (9CI);(S)-3-Amino-1-chloro-5-methyl-2-hexanone hydrochloride;Leu-CMK HCl;L-Leu-CMK·HCl;H-LEU-CHLOROMETHYLKETONE HCL;H-LEU-CMK HCL
• CAS NO: 54518-92-2
• Molecular Formula: C₇H₁₄ClNO*ClH
• Molecular Weight: 200.11
• Product Categories: Amino Acids;I - Z;Modified Amino Acids
• Mol File: 54518-92-2.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Storage Temp.: -15°C
• CAS DataBase Reference: L-LEUCINE CHLOROMETHYL KETONE HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: L-LEUCINE CHLOROMETHYL KETONE HYDROCHLORIDE(54518-92-2)
• EPA Substance Registry System: L-LEUCINE CHLOROMETHYL KETONE HYDROCHLORIDE(54518-92-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 54518-92-2(Hazardous Substances Data)

Usage

Chemical Properties

White solid

Uses

L-Leucine chloromethyl ketone HCl

Biochem/physiol Actions

L-Leucine chloromethyl ketone (Leu-CMK) is used as a lysosomal cysteine protease inhibitor and as an insulin-like stimulator of lipid synthesis. L-Leucine chloromethyl ketone (Leu-CMK) may be acetylated to generate acetylleucine chloromethyl ketone, an inhibitor of acylpeptide hydrolase.

Upstream product

• 75899-20-6 (C₅H₉O₂)(NHCHCOO)(CH₂C₃H₇)(CO₂C₂H₅) 
• 102123-85-3 (S)-1-chloro-2-oxo-3-(Boc-amino)-5-methylhexane 

Downstream Products

• 77076-37-0 {(S)-1-[(S)-1-(2-Chloro-acetyl)-3-methyl-butylcarbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester 
• 137150-30-2 C₄₆H₇₆N₈O₁₁ 
• 127231-48-5 Ac-Ser-Leu-Asn--Ile-Val-OMe 
• 127231-49-6 Ac-Leu-Asn--Ile-Val-OMe 
• 137150-38-0 [(S)-2-Benzyloxy-1-((S)-1-{(S)-2-carbamoyl-1-[(S)-1-(2-chloro-acetyl)-3-methyl-butylcarbamoyl]-ethylcarbamoyl}-3-methyl-butylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester 
• 137150-39-1 (S)-2-[(S)-2-((S)-2-Acetylamino-3-benzyloxy-propionylamino)-4-methyl-pentanoylamino]-N¹-[(S)-1-(2-chloro-acetyl)-3-methyl-butyl]-succinamide 
• 170028-11-2 Boc-D-Phe-Leu-CH₂Cl 

Relevant articles and documents

Amino Acids and Peptides. Part 48. Studies on the Structure of an Unexpected Reaction Product from Dipeptidyl Chloromethyl Ketone during Acid Hydrolysis

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Amino acids and peptides. XXXVI. Synthesis of enkephalin chloromethyl ketone and evaluation of its inhibitory activity against endopeptidase 22.19

Boc-Tyr-Gly-Gly-Phe-Leu-CH2Cl was synthesized by the conventional solution method. During the course of acid hydrolysis (6N HCl, 110°C, 18h) of Boc-Phe-Leu-CH2Cl, side reaction occurred, resulting in low recovery of Phe residue on amino acid analysis. The inhibitory activity of the synthesized Boc-Tyr-Gly-Gly-Phe-Leu-CH2Cl against endopeptidase 22.19, an enzyme related to the metabolism of opioid peptides, was examined.