4-Benzyl L-aspartate
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4-Benzyl L-aspartate

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Category
L-Amino Acids
Catalog number
BAT-004115
CAS number
2177-63-1
Molecular Formula
C11H13NO4
Molecular Weight
223.20
4-Benzyl L-aspartate
IUPAC Name
(2S)-2-amino-4-oxo-4-phenylmethoxybutanoic acid
Synonyms
L-Asp(OBzl)-OH; L-Aspartic acid b-benzyl ester; 4-Benzyl L-Aspartate; β-Benzyl L-Aspartate; L-Aspartic acid 4-benzylester; L-Aspartic acid 4-benzyl Ester
Appearance
White crystalline powder
Purity
≥ 98% (HPLC)
Density
1.283±0.06 g/cm3
Melting Point
196-208 °C
Boiling Point
413.1±45.0 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C11H13NO4/c12-9(11(14)15)6-10(13)16-7-8-4-2-1-3-5-8/h1-5,9H,6-7,12H2,(H,14,15)/t9-/m0/s1
InChI Key
VGALFAWDSNRXJK-VIFPVBQESA-N
Canonical SMILES
C1=CC=C(C=C1)COC(=O)CC(C(=O)O)N

4-Benzyl L-aspartate is a derivative of the naturally occurring amino acid aspartic acid, which is part of the class of benzylated amino acids. It consists of a benzyl group attached to the beta-carbon of the aspartate side chain. This modification gives 4-Benzyl L-aspartate distinct chemical properties compared to its non-benzylated counterpart. It is synthesized through various organic synthesis methods, making it a useful compound in a broad range of applications. The benzyl group alters its hydrophobicity and electronic characteristics, thereby expanding its utility in different chemical and biological contexts.

One of the key applications of 4-Benzyl L-aspartate is in the field of pharmaceuticals, especially in drug development and design. It serves as a building block in the synthesis of various pharmaceutical compounds, where its unique structure can be exploited to enhance the efficacy and specificity of drugs. The benzyl group’s presence often increases the lipophilicity of certain drugs, improving membrane permeability and thus bioavailability. This makes 4-Benzyl L-aspartate a valuable component in the creation of novel therapeutics aimed at targeting specific biochemical pathways and enhancing drug-like properties.

In addition to pharmaceuticals, 4-Benzyl L-aspartate is utilized extensively in biochemical research as a precursor for peptide synthesis. Its modified side chain provides researchers with the ability to manipulate peptide structures, facilitating the study of enzyme interactions and protein folding processes. The introduction of the benzyl group allows for more complex and diverse peptide macrocycles, which are crucial in investigating biological mechanisms and developing enzyme inhibitors. Utilizing 4-Benzyl L-aspartate in experimental setups helps in understanding the dynamics of protein structures and the role of peptides in biological systems.

Another significant application area is in the design of biosensors and molecular probes. 4-Benzyl L-aspartate can be used in the development of sensitive detection systems, primarily due to its ability to be further functionalized. By integrating this compound into sensor designs, researchers can improve the specificity and sensitivity of detection methods for various targets, including ions, small molecules, and proteins. The compound’s versatility in structural modification makes it a cornerstone in the innovation of biosensors aimed at providing real-time and accurate diagnostics in medical and environmental monitoring.

Finally, 4-Benzyl L-aspartate plays a role in the material sciences, particularly in the development of novel polymers and hydrogels. Its chemical structure can be incorporated into polymer chains to impart specific mechanical and chemical properties. For instance, the presence of the benzyl group can influence the hydrophobic/hydrophilic balance of polymer networks, making them suitable for applications such as drug delivery systems and tissue engineering scaffolds. By manipulating the molecular architecture of polymers with 4-Benzyl L-aspartate, researchers can create materials with enhanced performance characteristics tailored to specific industrial and biomedical applications.

1.Amino acids and peptides. XVIII. Dipeptide formation during the synthesis of Z-Asp(OBzl)-OH.
Iguchi S1, Kawasaki K, Okada Y. Int J Pept Protein Res. 1987 Nov;30(5):695-700.
During the benzyloxycarbonylation of H-Asp(OBzl)-OH by the Schotten-Bauman reaction with benzyloxycarbonyl chloride in the presence of NaHCO3 or Na2CO3, besides Z-Asp(OBzl)-OH, Z-Asp(OBzl)-Asp(OBzl)-OH was formed as side product, although the extent of the dipeptide formation differed depending on the base used (10% and 20% respectively). It was found that melting point, rotation value and Rf values upon thin-layer chromatography of Z-Asp(OBzl)-Asp(OBzl)-OH were quite similar to those of Z-Asp(OBzl)-OH.
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