4-[[[(1,1-Dimethylethyl)amino]carbonyl]amino]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-D-phenylalanine
[CAS# 1433975-21-3]

Identification

• Classification: Biochemical >> Amino acids and their derivatives
• Name: 4-[[[(1,1-Dimethylethyl)amino]carbonyl]amino]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-D-phenylalanine
• Synonyms: (2R)-3-[4-(tert-butylcarbamoylamino)phenyl]-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
• Molecular Formula: C₂₉H₃₁N₃O₅
• Molecular Weight: 501.57
• CAS Registry Number: 1433975-21-3
• SMILES: CC(C)(C)NC(=O)NC1=CC=C(C=C1)C[C@H](C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24

Properties

• Solubility: Insoluble (8.5E^-5 g/L) (25 ºC), Calc.^*
• Density: 1.270±0.06 g/cm³ (20 ºC 760 Torr), Calc.^*
• Index of Refraction: 1.628, Calc.^*
• Boiling Point: 699.0±55.0 ºC (760 mmHg), Calc.^*
• Flash Point: 376.5±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-P305+P351+P338

Discovory and Applicatios

4-[[[(1,1-Dimethylethyl)amino]carbonyl]amino]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-D-phenylalanine, commonly referred to as Fmoc-D-Phe(But)-NH2, is a synthetic amino acid derivative notable for its applications in peptide synthesis and drug development. This compound is a modified form of the natural amino acid phenylalanine, featuring a fluorenylmethoxycarbonyl (Fmoc) protecting group and a tert-butyl (But) substituent.

The discovery of Fmoc-D-Phe(But)-NH2 is linked to the broader research efforts in peptide chemistry that gained momentum in the late 20th century. The Fmoc protection strategy was developed as a means to enhance the efficiency and selectivity of peptide synthesis. The use of Fmoc groups allows for the solid-phase synthesis of peptides, facilitating the stepwise addition of amino acids while protecting the amino group from unwanted reactions.

In terms of applications, Fmoc-D-Phe(But)-NH2 plays a crucial role in the synthesis of various peptides, including those with pharmaceutical significance. The Fmoc protecting group can be easily removed under mild basic conditions, making it advantageous for creating peptide chains without the need for harsh reagents that could potentially damage sensitive functional groups.

One of the primary applications of Fmoc-D-Phe(But)-NH2 is in the development of peptide-based therapeutics. Peptides are increasingly recognized for their potential as drug candidates due to their specificity and lower toxicity compared to traditional small-molecule drugs. Fmoc-D-Phe(But)-NH2 is used to synthesize peptides that may act as inhibitors or modulators of biological pathways, thereby contributing to the treatment of various diseases, including cancer and metabolic disorders.

Additionally, this compound is also valuable in the design of peptidomimetics, which are peptide-like compounds that mimic the biological activity of peptides while offering improved stability and bioavailability. By utilizing Fmoc-D-Phe(But)-NH2 in the synthesis of peptidomimetics, researchers can create innovative therapeutic agents that maintain the desirable properties of peptides while overcoming some of their limitations.

Safety considerations for handling Fmoc-D-Phe(But)-NH2 include standard laboratory precautions, as the compound may cause irritation upon contact with skin or eyes. Adequate protective measures should be taken when handling this substance to ensure safe laboratory practices.

In summary, 4-[[[(1,1-Dimethylethyl)amino]carbonyl]amino]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-D-phenylalanine represents a significant advancement in peptide synthesis techniques. Its role in developing therapeutic peptides and peptidomimetics underscores its importance in the pharmaceutical field, where the demand for specific and effective treatments continues to grow.