4-(Aminocarbonyl)-N-[(1,1-dimethylethoxy)carbonyl]-2,6-dimethyl-L-phenylalanine
[CAS# 623950-02-7]

Identification

• Classification: Biochemical >> Amino acids and their derivatives >> Phenylalanine derivatives
• Name: 4-(Aminocarbonyl)-N-[(1,1-dimethylethoxy)carbonyl]-2,6-dimethyl-L-phenylalanine
• Synonyms: N-(tert-Butoxycarbonyl)-4-carbamoyl-2,6-dimethyl-L-phenylalanine
• Molecular Formula: C₁₇H₂₄N₂O₅
• Molecular Weight: 336.38
• CAS Registry Number: 623950-02-7
• EC Number: 633-600-1
• SMILES: CC1=CC(=CC(=C1C[C@@H](C(=O)O)NC(=O)OC(C)(C)C)C)C(=O)N

Properties

• Density: 1.201±0.1 g/cm³, Calc.^*
• Melting point: >210 °C
• Index of Refraction: 1.549, Calc.^*
• Boiling Point: 497.1±45.0 °C (760 mmHg), Calc.^*
• Flash Point: 254.4±28.7 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS06;GHS07 Danger
• Risk Statements: H301-H302-H311-H330-H331
• Safety Statements: P260-P261-P262-P264-P270-P271-P280-P284-P301+P316-P301+P317-P302+P352-P304+P340-P316-P320-P321-P330-P361+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	2	H330
Acute toxicity	Acute Tox.	3	H311
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

4-(Aminocarbonyl)-N-[(1,1-dimethylethoxy)carbonyl]-2,6-dimethyl-L-phenylalanine is a chemical compound with an interesting structure that is utilized in various biochemical and pharmaceutical research areas. It is a derivative of L-phenylalanine, an essential amino acid that plays a key role in protein synthesis and is involved in the biosynthesis of neurotransmitters like dopamine, norepinephrine, and epinephrine. This compound is designed to incorporate specific functional groups, including an aminocarbonyl group and a dimethylethoxycarbonyl protecting group, which make it particularly useful in synthetic biology and peptide synthesis.

The discovery of 4-(Aminocarbonyl)-N-[(1,1-dimethylethoxy)carbonyl]-2,6-dimethyl-L-phenylalanine was part of a broader effort to develop specialized amino acid derivatives for use in peptide-based drug design and other biotechnological applications. The modification of L-phenylalanine with a dimethylethoxycarbonyl group helps protect the amine group during peptide synthesis, which is a critical step in controlling the formation of desired peptide sequences. The addition of the aminocarbonyl group further enhances the compound’s versatility, allowing it to be incorporated into a variety of peptide sequences that require additional functional groups for specific chemical or biological activity.

The main application of 4-(Aminocarbonyl)-N-[(1,1-dimethylethoxy)carbonyl]-2,6-dimethyl-L-phenylalanine is in the field of peptide synthesis, where it serves as a key intermediate for the production of peptides with specific biological activities. The protective groups incorporated into the structure allow for more efficient and controlled synthesis of peptides, particularly those that need to undergo stepwise elongation. These peptides can be used for a wide range of applications, including therapeutic peptides, enzyme inhibitors, and molecular probes. Furthermore, the modifications to the L-phenylalanine backbone enable the synthesis of peptides with enhanced stability, bioactivity, or selectivity, which is especially useful in drug development.

This compound also has potential applications in drug discovery, particularly in the design of peptide-based therapeutics targeting specific receptors or enzymes. The ability to introduce functional groups like aminocarbonyl and dimethylethoxycarbonyl into peptides provides chemists with a powerful tool to fine-tune the properties of therapeutic peptides, such as their binding affinity, stability, and bioavailability. As a result, 4-(Aminocarbonyl)-N-[(1,1-dimethylethoxy)carbonyl]-2,6-dimethyl-L-phenylalanine is a valuable compound in the ongoing search for more effective peptide-based drugs.

In addition to its applications in peptide synthesis and drug discovery, the compound’s unique chemical structure may also have implications in the development of biomaterials and other biologically relevant materials. The incorporation of modified amino acids into synthetic peptides and proteins could lead to the creation of novel biomaterials with improved properties, such as enhanced biodegradability, specific receptor targeting, or greater resistance to enzymatic degradation. This makes 4-(Aminocarbonyl)-N-[(1,1-dimethylethoxy)carbonyl]-2,6-dimethyl-L-phenylalanine an important compound for advancing research in both biotechnology and pharmaceutical sciences.

References

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