4-[(Aminocarbonyl)amino]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-D-phenylalanine
[CAS# 324017-22-3]

Identification

• Classification: Biochemical >> Amino acids and their derivatives
• Name: 4-[(Aminocarbonyl)amino]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-D-phenylalanine
• Synonyms: (2R)-3-[4-(carbamoylamino)phenyl]-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
• Protein Sequence: X
• Molecular Formula: C₂₅H₂₃N₃O₅
• Molecular Weight: 445.47
• CAS Registry Number: 324017-22-3
• EC Number: 811-283-2
• SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)N[C@H](CC4=CC=C(C=C4)NC(=O)N)C(=O)O

Properties

• Solubility: Insoluble (3.5E^-3 g/L) (25 ºC), Calc.^*
• Density: 1.376±0.06 g/cm³ (20 ºC 760 Torr), Calc.^*
• Melting point: 163 ºC (decomp)^**
• Index of Refraction: 1.675, Calc.^*
• Boiling Point: 699.1±55.0 ºC (760 mmHg), Calc.^*
• Flash Point: 376.6±31.5 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Discovory and Applicatios

4-[(Aminocarbonyl)amino]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-D-phenylalanine, commonly referred to as Fmoc-D-Phe-Arg(O)-NH2, is a significant compound in the realm of peptide chemistry and drug development. The discovery of this molecule can be traced back to the advancements in solid-phase peptide synthesis (SPPS) in the late 20th century. SPPS revolutionized peptide chemistry by allowing for the efficient and systematic construction of peptides, thereby enabling the synthesis of complex bioactive compounds.

The compound itself is a derivative of D-phenylalanine, an amino acid that plays a crucial role in protein synthesis and is known for its involvement in various biological processes. The incorporation of the fluorenylmethoxycarbonyl (Fmoc) protective group provides stability and solubility, facilitating its use in peptide synthesis. The design of this compound reflects the growing interest in amino acid derivatives that possess enhanced pharmacological properties, particularly in the context of targeted therapy and drug delivery.

4-[(Aminocarbonyl)amino]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-D-phenylalanine is primarily utilized in the synthesis of peptide-based therapeutics. The Fmoc group allows for selective deprotection during the peptide synthesis process, enabling the stepwise addition of amino acids to create longer peptide chains. This methodology has significant implications in developing peptide hormones, vaccines, and other biologically active compounds. The unique properties of this molecule, combined with its ease of incorporation into larger peptides, make it a valuable building block for pharmaceutical applications.

In addition to its role in peptide synthesis, the compound has been explored for its potential therapeutic applications. Studies indicate that peptides containing D-phenylalanine derivatives exhibit various biological activities, including analgesic and anti-inflammatory effects. The structural modifications provided by the aminocarbonyl group further enhance the pharmacological profile of the resulting peptides, making them suitable candidates for developing novel therapeutics.

Moreover, the potential use of Fmoc-D-Phe-Arg(O)-NH2 in drug delivery systems has garnered interest in the pharmaceutical field. Peptides derived from this compound can be engineered to improve the solubility, stability, and bioavailability of therapeutic agents, addressing critical challenges in drug formulation. This versatility opens avenues for utilizing peptide conjugates in targeted therapy, particularly in cancer treatment, where precision and efficacy are paramount.

In summary, 4-[(Aminocarbonyl)amino]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-D-phenylalanine represents a pivotal advancement in peptide chemistry, with significant implications for drug development and therapeutic applications. Its discovery has contributed to the evolution of synthetic methodologies in biochemistry, and its potential in developing innovative therapeutics continues to be a focus of scientific research.