24959-68-0

Basic information

• Product Name: Z-ALA-LEU-OH
• Synonyms: CBZ-L-ALA-LEU;N-CBZ-ALA-LEU;N-BENZYLOXYCARBONYL-L-ALANYL-L-LEUCINE;N-CARBOBENZOXY-L-ALANYL-L-LEUCINE;Z-L-ALANYL-L-LEUCINE;Z-ALA-LEU-OH;Z-ALA-LEU;N-carbobenzyloxy-Ala-Leu
• CAS NO: 24959-68-0
• Molecular Formula: C₁₇H₂₄N₂O₅
• Molecular Weight: 336.38
• Product Categories: Amino Acid Derivatives;Dipeptides;Dipeptides and Tripeptides;Peptides
• Mol File: 24959-68-0.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 581.7±45.0 °C(Predicted)
• Appearance: /
• Density: 1.181
• Storage Temp.: −20°C
• PKA: 3.49±0.10(Predicted)
• CAS DataBase Reference: Z-ALA-LEU-OH(CAS DataBase Reference)
• NIST Chemistry Reference: Z-ALA-LEU-OH(24959-68-0)
• EPA Substance Registry System: Z-ALA-LEU-OH(24959-68-0)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 24959-68-0(Hazardous Substances Data)

Usage

General Description

Z-ALA-LEU-OH, also known as N-acetyl-L-tyrosine ethyl ester, is a synthetic chemical compound with potential biological and pharmaceutical applications. It is a peptide derived from the amino acids alanine and leucine, and is typically used as a building block in the synthesis of larger peptides or proteins. Z-ALA-LEU-OH is commonly employed in research and development of new drug compounds, particularly as part of drug formulation studies or as a reference standard in chemical analysis. Additionally, this chemical may have potential therapeutic uses due to its ability to interact with biological systems, such as in the development of targeted drug delivery systems or in the study of enzyme-substrate interactions. Overall, Z-ALA-LEU-OH is a versatile chemical tool with diverse applications in the fields of pharmaceuticals and biomedical research.

Upstream product

• 203640-41-9 Z-L-Ala 2,2,2-trifluoroethyl ester 
• 1142-20-7 N-Cbz-Ala 
• 2443-71-2 benzyl (S)-(1-hydrazineyl-3-methyl-1-oxobutan-2-yl)carbamate 
• 2743-60-4 L-Leucine ethyl ester 
• 41041-70-7 Benzyloxycarbonyl-L-alanyl-L-leucinethylester 

Downstream Products

• 167414-27-9 (2S,3R)-3-Benzyloxy-2-((S)-2-{(S)-2-[(S)-2-((S)-2-benzyloxycarbonylamino-propionylamino)-4-methyl-pentanoylamino]-3-carboxy-propionylamino}-4-methyl-pentanoylamino)-butyric acid allyl ester 
• 269079-86-9 (N-Benzyloxycarbonyl-L-alanyl-L-leucyl)diazomethane 
• 1803-60-7 (3S,6S)-3-methyl-6-(2-methylpropyl)piperazine-2,5-dione 
• 4864-39-5 N-carbobenzoxy-L-alanyl-L-leucine methyl ester 
• 204992-90-5 (2S,3R)-3-Benzyloxy-2-{(S)-2-[(S)-2-[(S)-2-((S)-2-benzyloxycarbonylamino-propionylamino)-4-methyl-pentanoylamino]-3-(4-methoxy-benzyloxycarbonyl)-propionylamino]-4-methyl-pentanoylamino}-butyric acid allyl ester 
• 204992-89-2 (S)-N-[(S)-1-((S)-1-Allyloxycarbonyl-2-benzyloxy-ethylcarbamoyl)-3-methyl-butyl]-3-[(S)-2-((S)-2-benzyloxycarbonylamino-propionylamino)-4-methyl-pentanoylamino]-succinamic acid 4-methoxy-benzyl ester 
• 128228-44-4 [(S)-1-((S)-4-Isobutyl-5-oxo-4,5-dihydro-oxazol-2-yl)-ethyl]-carbamic acid benzyl ester 

Relevant articles and documents

Enzymatic synthesis of activated esters and their subsequent use in enzyme-based peptide synthesis

Chemoenzymatic peptide synthesis is potentially the most cost-efficient technology for the synthesis of short and medium-sized peptides. However, there are still some limitations when challenging peptides, e.g. containing sterically demanding acyl donors, non-proteinogenic amino acids or proline residues, are to be synthesized. To remedy these limitations, special ester moieties have been used that are specifically recognized by the enzyme, e.g. guanidinophenyl, carboxamidomethyl (Cam) or trifluoroethyl (Tfe) esters, which, unfortunately, are notoriously difficult to synthesize chemically. Herein, we demonstrate that Cam and Tfe esters are very useful for Alcalase-CLEA mediated peptide synthesis using sterically demanding and non-proteinogenic acyl donors as well as poor nucleophiles, and combinations thereof. Furthermore, these esters can be efficiently synthesized by using the lipase Cal-B or Alcalase-CLEA. Finally, it is shown that the ester synthesis by Cal-B and subsequent peptide synthesis by Alcalase-CLEA can be performed simultaneously using a two-enzyme-one-pot approach with glycolamide or 2,2,2-trifluoroethanol as additive.