200123-51-9

Basic information

• Product Name: H-DL-LEU-OBZL P-TOSYLATE
• Synonyms: H-DL-LEU-OBZL P-TOSYLATE;H-DL-Leu-OBzl.TosOH;H-DL-Leu-OBzl;benzyl 2-amino-4-methylpentanoate
• CAS NO: 200123-51-9
• Molecular Formula: C₇H₈O₃S*C₁₃H₁₉NO₂
• Molecular Weight: 393.5
• Mol File: 200123-51-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: H-DL-LEU-OBZL P-TOSYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: H-DL-LEU-OBZL P-TOSYLATE(200123-51-9)
• EPA Substance Registry System: H-DL-LEU-OBZL P-TOSYLATE(200123-51-9)

Safety Data

• Hazardous Substances Data: 200123-51-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
H-DL-LEU-OBZL P-TOSYLATE is used as a research tool for investigating the role of aminopeptidases in various biological pathways. Its reversible inhibition of these enzymes allows for the study of their functions and the impact of their inhibition on different physiological processes.
Used in Therapeutic Intervention:
H-DL-LEU-OBZL P-TOSYLATE has potential as a target for therapeutic intervention in diseases such as cancer and cardiovascular disorders. By inhibiting aminopeptidases, it may help regulate the activity of these enzymes and contribute to the treatment or management of these conditions.
Used in Drug Development:
As a reversible inhibitor of aminopeptidases, H-DL-LEU-OBZL P-TOSYLATE can be utilized in the development of drugs that target these enzymes. Its ability to modulate the activity of aminopeptidases may lead to the creation of novel therapeutic agents for the treatment of various diseases.

Upstream product

• 104-15-4 toluene-4-sulfonic acid 
• 328-39-2 LEUCINE 
• 100-51-6 benzyl alcohol 

Downstream Products

• 14390-37-5 N-Diphenylphosphoro-DL-leucin-benzylester 
• 246506-79-6 (S)-benzyl 2-((2S,3R)-3-((tert-butoxycarbonyl)amino)-2-hydroxy-4-phenylbutanamido)-4-methylpentanoate 

Relevant articles and documents

One-step preparation of enantiopure l- or d-amino acid benzyl esters avoiding the use of banned solvents

The enantiomers of amino acid benzyl esters are very important synthetic intermediates. Many of them are currently prepared by treatment with benzyl alcohol and p-toluenesulfonic acid in refluxing benzene or carbon tetrachloride, to azeotropically remove water, and then precipitated as tosylate salt by adding diethyl ether. Here, we report a very efficient preparation of eight l- or d-amino acid benzyl esters (Ala, Phe, Tyr, Phg, Val, Leu, Lys, Ser), in which these highly hazardous solvents are dismissed using cyclohexane as a water azeotroping solvent and ethyl acetate to precipitate the tosylate salt. With some work-up modifications and lower yield, the procedure can be applied also to methionine. Chiral HPLC analysis shows that all the benzyl esters, including the highly racemizable ones such as those of phenylglycine, tyrosine and methionine, are formed enantiomerically pure under these new reaction conditions thus validating the solvents replacement. Contrariwise, toluene cannot be used in place of benzene or carbon tetrachloride because leading to partially or totally racemized amino acid benzyl esters depending on the polar effect of the amino acid α-side chain as expressed by Taft’s substituent constant (σ*).

Threonyl-valyline leucine containing peptides and pharmaceutical compositions

Polypeptides, omega-N-acylated and/or hydrocarbon-containing esters or amides of polypeptides are useful in the treatment of schizophrenia. The polypeptide-containing materials have a characteristic T-V-L structure, i.e., STR1 The preferred compositions are N-acylated T-V-L containing polypeptides, especially amides.