Benzyloxycarbonylserine丨CAS 1145-80-8

Benzyloxycarbonylserine丨CAS 1145-80-8
Product Introduction:
Catalog No.: SS128613
CAS No.: 1145-80-8
Purity(HPLC): 98.0%min
Product Name: Benzyloxycarbonylserine
Molecular Formula: C11H13NO5
Molecular Weight: 239.23
Synonym(s): N-Cbz-L-Serine
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Technical Parameters
Description

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Specifications of Benzyloxycarbonylserine丨CAS 1145-80-8

 

Item

Specification

Appearance

White to off-white powder

IR Spectrum

In accordance with structure

Solubility

0.1g in 2ml MeOH clearly soluble

Specific Rotation

[α]D20: +5.5±1.5° (C=4, AcOH)

Water (K.F.)

1.0% max

Purity (HPLC)

98.0% min

 

Transport Information of Benzyloxycarbonylserine丨CAS 1145-80-8

 

Parameter

Specification

UN Number

 

Class

 

Packing Group

 

H.S. Code

2933990099306

Stability & Reactivity

The product is chemically stable under standard ambient conditions (room temperature).

Storage

Tightly closed. Store in a closed, dry, ventilated place

Condition to Avoid

Keep away moisture. Strong heating.

Package

As per request

 

Manufacturing Information of Benzyloxycarbonylserine丨CAS 1145-80-8

 

Parameter

Specification

Capacity

 

Frequency

 

Main Export Countries

 

Capacity/Batch

200kg/batch

Experience

Production since 2019, custom available

Stock

 
Overview

 

Benzyloxycarbonylserine丨CAS 1145-80-8 (Z-Serine) is a protected amino acid commonly used in peptide synthesis and organic chemistry. The benzyloxycarbonyl (Z) group, a common protecting group, is used to mask the hydroxyl group of serine, preventing unwanted reactions during peptide synthesis or other synthetic procedures. Once the desired reaction or synthesis is complete, the protective group can be removed under mild conditions, allowing the serine's hydroxyl group to be exposed for further functionalization or incorporation into peptides.

 

Applications of Benzyloxycarbonylserine丨CAS 1145-80-8

 

1. Peptide Synthesis
● Protecting Group in Peptide Synthesis: Benzyloxycarbonylserine丨CAS 1145-80-8 is widely used in solid-phase peptide synthesis (SPPS) and solution-phase peptide synthesis to protect the serine residue while synthesizing peptides. The benzyloxycarbonyl group is particularly useful because it is easily removed by hydrogenation or acidic treatment, revealing the serine's free hydroxyl group for subsequent reactions or peptide elongation.
● Selective Protection: The Z-group offers selectivity and efficiency in protecting serine during the peptide assembly process, preventing side reactions that could interfere with the desired peptide product.

2. Synthesis of Bioactive Peptides
● Bioactive Peptides: Benzyloxycarbonylserine丨CAS 1145-80-8 is an essential building block for the synthesis of bioactive peptides, including those with roles in enzyme inhibition, signal transduction, and drug development. The protection of the serine residue ensures that it remains intact during peptide chain assembly, allowing for the production of peptides with specific functionalities.
● Therapeutic Peptides: It is used to synthesize therapeutic peptides where serine plays a role in maintaining specific biological activities or functions. For instance, peptides designed to interact with proteins or enzymes in biological pathways often require careful synthesis, and Z-serine serves as a key component in those processes.

3. Drug Design and Development
● Prodrug Design: The protected serine can be incorporated into the structure of prodrugs-pharmaceutical compounds that are metabolized in the body to release an active drug. Z-Serine derivatives can be part of prodrug molecules designed for controlled release of active pharmaceutical agents.
● Molecular Modeling and Drug Design: Z-serine can also be used as part of the structure of molecular models designed for testing and optimizing interactions between peptides and biological targets, contributing to drug discovery.

4. Research Applications in Protein Chemistry
● Protein Modification and Functionalization: Z-serine can be used in the modification of protein structures, where the serine side chain is modified without disrupting the overall protein folding. It can also be incorporated into peptide libraries used to screen for new bioactive compounds or protein-ligand interactions.
● Enzyme Inhibitors: Serine is involved in the active sites of various enzymes, particularly serine proteases. Z-serine is used in the design and synthesis of serine protease inhibitors or in studying enzyme activity where serine's role in catalysis is crucial.

5. Chemical Reactions and Synthesis of Derivatives
● Organic Synthesis: Z-serine is a versatile intermediate in organic chemistry, useful for the synthesis of various serine derivatives. These derivatives can have applications in pharmaceuticals, material science, and biochemistry.
● Synthesis of Functionalized Compounds: Once the Z-group is removed, the free serine residue can be used to create functionalized compounds such as phosphoserine, glycosylated serine, or methylated serine derivatives for further chemical reactions or biological studies.

 

Benefits of Benzyloxycarbonylserine丨CAS 1145-80-8

 

√ Efficient Protection for Serine Residues
● The benzyloxycarbonyl (Z) group offers a highly efficient protection strategy for serine in peptide synthesis. This protection allows the amino acid to be safely incorporated into the growing peptide chain without interfering with the chemical reactions or side reactions.
√ Selective and Mild Deprotection
● Benzyloxycarbonylserine丨CAS 1145-80-8 is valued for its mild deprotection conditions, making it easier to remove the Z-group without affecting the overall peptide or compound. Hydrogenation or acidic treatment are commonly used to remove the protective group, leaving the serine residue free for further reactions.
√ Wide Application in Peptide Synthesis
● Z-serine is widely used in both solid-phase and solution-phase peptide synthesis because of its versatility and compatibility with a range of synthetic methods. This makes it ideal for the synthesis of therapeutic peptides and bioactive molecules.
√ Facilitates Synthesis of Bioactive and Therapeutic Peptides
● By enabling the precise control of serine's involvement in peptide synthesis, Z-serine ensures that bioactive peptides and therapeutic peptides are synthesized correctly and efficiently. This is critical in developing peptides that act as drugs or molecular probes.
√ Useful in Drug Discovery and Prodrug Development
● Z-serine can be incorporated into the structure of prodrugs, enabling targeted drug delivery and controlled release of active pharmaceutical ingredients, which enhances drug efficacy and bioavailability.
√ Versatile Synthetic Intermediate
● The compound serves as a versatile synthetic intermediate, offering chemists a reliable building block for diverse chemical reactions. This makes it a useful reagent in the creation of complex serine derivatives, important for drug development and biochemical research.

 

Conclusion
Benzyloxycarbonylserine丨CAS 1145-80-8 is a key protected amino acid widely used in peptide synthesis, drug design, and organic chemistry. Its ability to selectively protect the hydroxyl group of serine makes it essential in the formation of bioactive peptides and complex molecules. With its versatility in synthesis, easy deprotection methods, and broad applications in pharmaceutical research, enzyme studies, and drug development, benzyloxycarbonylserine is an invaluable tool in the field of chemistry and drug discovery.

Would you like more information on peptide synthesis protocols, or perhaps details on the deprotection methods for Z-serine?

 

 

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