N-α-Carbobenzoxy-D-homocitrulline
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N-α-Carbobenzoxy-D-homocitrulline

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Category
CBZ-Amino Acids
Catalog number
BAT-006912
CAS number
218938-56-8
Molecular Formula
C15H21N3O5
Molecular Weight
323.35
N-α-Carbobenzoxy-D-homocitrulline
IUPAC Name
(2R)-6-(carbamoylamino)-2-(phenylmethoxycarbonylamino)hexanoic acid
Synonyms
Z-D-homoCit-OH; Z-D-Lys(Carbamoyl)-OH; N-α-Carbobenzoxy-N-ε-carbamoyl-D-lysine
Purity
99%
Density
1.3±0.1 g/cm3
Boiling Point
574.7±50.0 °C at 760 mmHg
Storage
Store at -20 °C
InChI
InChI=1S/C15H21N3O5/c16-14(21)17-9-5-4-8-12(13(19)20)18-15(22)23-10-11-6-2-1-3-7-11/h1-3,6-7,12H,4-5,8-10H2,(H,18,22)(H,19,20)(H3,16,17,21)/t12-/m1/s1
InChI Key
GDAQVXISDUMUJG-GFCCVEGCSA-N
Canonical SMILES
C1=CC=C(C=C1)COC(=O)NC(CCCCNC(=O)N)C(=O)O

N-α-Carbobenzoxy-D-homocitrulline is a unique compound that falls under the category of modified amino acids. It is characterized by the presence of an N-α-Carbobenzoxy protective group attached to the D-isomer of homocitrulline. This protective group is commonly used in peptide synthesis to prevent unwanted reactions at specific sites during the complex synthesis of peptides and proteins. The presence of the D-isomer is significant as it imparts resistance to proteolytic enzymes, making it valuable in various biological and chemical contexts. The carbobenzoxy group, also known as the Z-group, is an N-protecting group commonly used in organic synthesis to protect the amine functionality in amino acids, allowing selective reactions to occur elsewhere in the molecule.

One of the primary applications of N-α-Carbobenzoxy-D-homocitrulline lies in the field of pharmaceutical research and development. This compound is utilized in the synthesis of therapeutic peptides, which are increasingly important in the development of modern medicines. Due to its ability to resist enzymatic degradation, it contributes to the stability and bioavailability of peptide-based drugs. The use of N-α-Carbobenzoxy-D-homocitrulline in drug design facilitates the creation of peptide drugs that can act as enzyme inhibitors, receptor agonists or antagonists, providing precise control over biological processes and offering novel treatment approaches for various diseases.

Another significant application of N-α-Carbobenzoxy-D-homocitrulline is in the realm of biochemical studies. Researchers employ this compound in the investigation of protein-protein interactions and protein-ligand interactions due to its ability to mimic natural substrates while offering enhanced stability. The compound’s resistance to enzymatic action allows scientists to conduct detailed studies without the complication of rapid degradation. This is particularly useful in the study of enzyme mechanisms, where understanding the duration and dynamics of substrate interaction is critical.

In the field of synthetic biology, N-α-Carbobenzoxy-D-homocitrulline serves as a building block for the construction of novel biomolecules and materials. It is used in the design of synthetic peptides that can self-assemble into nanostructures, which have applications in drug delivery systems, tissue engineering, and the development of new biomaterials. By utilizing this compound, researchers can create peptides with specific properties such as enhanced solubility, stability, or targeting ability, which are essential for the advancement of medical and biotechnological applications.

Lastly, N-α-Carbobenzoxy-D-homocitrulline finds application in the agrochemical industry. It is incorporated into the design of novel agrochemicals that aim to improve crop protection and yield. By modifying the resistance of these compounds to enzymatic breakdown, researchers can create more effective and durable agrochemical solutions. Furthermore, this compound’s role in studying protein-ligand interactions can lead to the discovery of new biological pathways critical for plant growth and disease resistance, contributing to sustainable agricultural practices.

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