Discover the Versatility of Z-Cys(Bzl)-ONp in Peptide Synthesis

Discover the Versatility of Z-Cys(Bzl)-ONp in Peptide Synthesis

Dr. Rashmi Ranjan Mohanty

by Dr. Rashmi Ranjan Mohanty


In the world of peptide synthesis, certain molecules play an essential role in the formation of peptide bonds, and Z-Cys(Bzl)-ONp is one of these vital intermediates. Advent's Molecule of the Month, Z-Cys(Bzl)-ONp, stands as a perfect example of a compound designed to simplify and improve the efficiency of peptide synthesis, a critical process in the development of pharmaceuticals, research chemicals, and therapeutic peptides.

This detailed overview explores the chemical properties, synthesis, applications, and advantages of using Z-Cys(Bzl)-ONp in both solution-phase and solid-phase peptide synthesis.

What Is Z-Cys(Bzl)-ONp?

Z-Cys(Bzl)-ONp, also known as N-carbobenzyloxy-S-benzyl-L-cysteine 4-nitrophenyl ester, is a specialized molecule that serves as an intermediate in the synthesis of peptides. Peptides are chains of amino acids linked by peptide bonds, and their formation requires highly efficient and controlled conditions to ensure specificity and purity. Z-Cys(Bzl)-ONp is an activated ester that plays a pivotal role in the coupling reaction, where it facilitates the bond formation between cysteine and another amino acid residue.

The structure of Z-Cys(Bzl)-ONp is designed to protect both the amino and thiol groups of cysteine, ensuring that no unwanted side reactions occur during the synthesis process. The Z (benzyloxycarbonyl) group protects the amino group of cysteine, while the Bzl (benzyl) group shields the thiol group. These protecting groups are crucial in preserving the reactivity of the functional groups during the peptide chain assembly, thereby allowing efficient and controlled synthesis.

Molecule Details - Z-Cys(Bzl)-ONp

Property

Details

Molecule Name

Z-Cys(Bzl)-ONp

IUPAC Name

Z-S-benzyl-L-cysteine 4-nitrophenyl ester; N-Carbobenzyloxy-S-benzyl-L-cysteine 4-nitrophenyl ester; 4-Nitrophenyl (2R)-2-{[(benzyloxy)carbonyl]amino}-3-(benzylthio)propanoate

Molecular Formula (MF)

C24H22N2O6S

Molecular Weight (MW)

466.51 g/mol

CAS Number

3401-37-4

Advent Product Code

77983

Structure

Purity

>98%


How Does Z-Cys(Bzl)-ONp Work in Peptide Synthesis?

Peptide synthesis involves two main techniques: solution-phase synthesis and solid-phase synthesis. Both approaches rely on activated esters like Z-Cys(Bzl)-ONp to facilitate the formation of peptide bonds.

  1. Solution-phase peptide synthesis: In this method, peptides are synthesized in a liquid phase, where the amino acids are dissolved in a solvent and react with each other. The role of Z-Cys(Bzl)-ONp here is to activate cysteine, making it highly reactive for coupling with another amino acid residue.

  2. Solid-phase peptide synthesis (SPPS): Unlike solution-phase synthesis, SPPS involves the attachment of the peptide chain to a solid resin. Z-Cys(Bzl)-ONp can be used to activate cysteine, allowing it to couple with the growing peptide chain that is anchored to the resin. This technique is advantageous because it allows the peptides to be synthesized in a stepwise manner, with each cycle adding one amino acid at a time.

The presence of the Z and Bzl protecting groups ensures that the reaction proceeds smoothly by preventing unwanted side reactions. These groups are later removed after the peptide chain has been completed, leaving behind the pure peptide of interest.

Applications in Pharmaceutical and Biotechnological Research

Z-Cys(Bzl)-ONp is particularly valuable in the pharmaceutical industry and research laboratories that are focused on peptide-based therapeutics. Peptides are increasingly being used as drugs for a wide range of conditions, including cancer, diabetes, and autoimmune diseases. Since the demand for high-purity peptides is on the rise, Z-Cys(Bzl)-ONp serves as an essential building block in the synthesis of these biologically active molecules.

The molecule’s high purity (>98%) ensures that the resulting peptides are of the highest quality, with minimal impurities that could compromise the efficacy of the peptide drug. The purity of Z-Cys(Bzl)-ONp is determined using advanced techniques like 1H NMR, Mass Spectrometry, IR Spectroscopy, and TGA (Thermogravimetric Analysis), which are standard characterization methods in the chemical industry to confirm the structural integrity and purity of compounds.

Key Features and Advantages of Z-Cys(Bzl)-ONp

  • High Purity: Z-Cys(Bzl)-ONp is manufactured with a purity greater than 98%, making it suitable for sensitive applications where high-quality intermediates are required.

  • Versatility: This molecule is effective in both solution-phase and solid-phase peptide synthesis, providing researchers with the flexibility to choose the appropriate method for their peptide synthesis needs.

  • Protection of Functional Groups: The protective Z and Bzl groups prevent undesired reactions and side reactions, ensuring a more efficient and cleaner synthesis process.

  • Global Availability: Advent provides Z-Cys(Bzl)-ONp to both domestic and international markets, serving the growing global demand for high-quality peptide intermediates and working standards.

  • Comprehensive Characterization: Each batch of Z-Cys(Bzl)-ONp is backed by a full suite of characterization data, including 1H NMR, Mass Spectrometry, and IR spectra, ensuring transparency and reliability for customers.

The Importance of Z-Cys(Bzl)-ONp in Peptide Therapeutics

The use of Z-Cys(Bzl)-ONp in peptide synthesis is instrumental in the growing field of peptide therapeutics. Peptides are gaining prominence due to their ability to target specific biological pathways with high precision and minimal side effects. Unlike small molecule drugs, peptides are large, complex molecules that can bind to a wide variety of biological targets, including enzymes, receptors, and antibodies.

Z-Cys(Bzl)-ONp aids in the efficient and controlled production of these peptides, making it a key component in the manufacture of peptide-based drugs. As more pharmaceutical companies turn to peptide therapeutics, the demand for high-quality peptide synthesis intermediates like Z-Cys(Bzl)-ONp is expected to grow.

A Reliable Partner for Pharma and Research Laboratories

As a leading provider of chemical intermediates and working standards, Advent continues to support its customers with high-quality products like Z-Cys(Bzl)-ONp. With its focus on purity, versatility, and global accessibility, Z-Cys(Bzl)-ONp remains an indispensable tool for researchers and pharmaceutical companies involved in peptide synthesis. Whether you're working on small-scale research projects or large-scale pharmaceutical production, Advent's Molecule of the Month is a reliable partner in advancing peptide science.

In conclusion, Z-Cys(Bzl)-ONp exemplifies the innovative approach that Advent takes to support the chemical and pharmaceutical industries. By providing high-purity intermediates, Advent ensures that researchers and pharmaceutical manufacturers have access to the tools they need to develop the next generation of peptide-based drugs.



Dr. Rashmi Ranjan Mohanty

by Dr. Rashmi Ranjan Mohanty