N-Fmoc-N'-Boc-N'-isopropyl-L-lysine
[CAS# 201003-48-7]

Identification

• Classification: Biochemical >> Amino acids and their derivatives >> Lysine derivative
• Name: N-Fmoc-N'-Boc-N'-isopropyl-L-lysine
• Synonyms: Fmoc-Lys(Boc)(isopropyl)-OH; N-(9-Fluorenylmethyloxycarbonyl)-N'-tert-butoxycarbonyl-N'-isopropyl-L-lysine
• Molecular Formula: C₂₉H₃₈N₂O₆
• Molecular Weight: 510.62
• CAS Registry Number: 201003-48-7
• EC Number: 695-297-2
• SMILES: CC(C)N(CCCC[C@@H](C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13)C(=O)OC(C)(C)C

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.558, Calc.^*
• Boiling Point: 677.1±55.0 °C (760 mmHg), Calc.^*
• Flash Point: 363.3±31.5 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

N-Fmoc-N'-Boc-N'-isopropyl-L-lysine is a modified amino acid that has garnered attention in the fields of organic chemistry and peptide synthesis. Its discovery is part of the broader exploration of amino acid derivatives, which are essential for developing peptides and proteins with specific functional characteristics. The Fmoc (9-fluorenylmethoxycarbonyl) and Boc (tert-butyloxycarbonyl) protecting groups allow for selective modifications during the synthesis of peptides, offering chemists the ability to control reactivity and improve yields.

The compound’s unique structure, featuring both Fmoc and Boc protective groups on the lysine side chain, provides several advantages in peptide synthesis. The Fmoc group serves as a protective group that can be easily removed under mild basic conditions, allowing for the subsequent coupling of other amino acids. The Boc group, on the other hand, can be removed using acidic conditions, providing flexibility in the synthetic strategy. The isopropyl group contributes to steric hindrance, which can influence the conformation and reactivity of the peptide during synthesis.

N-Fmoc-N'-Boc-N'-isopropyl-L-lysine is widely used in solid-phase peptide synthesis (SPPS), a powerful technique for assembling peptides in a stepwise manner on a solid support. This compound facilitates the incorporation of lysine into peptides while maintaining the ability to introduce other functional groups through its reactive amine. The versatility of N-Fmoc-N'-Boc-N'-isopropyl-L-lysine makes it an attractive building block in designing bioactive peptides, therapeutic agents, and peptide-based drugs.

In addition to its applications in peptide synthesis, N-Fmoc-N'-Boc-N'-isopropyl-L-lysine has implications in research focused on drug delivery systems and biomaterials. The ability to create peptides with specific functionalities can lead to the development of novel therapeutic agents that target particular biological pathways or receptors.

Overall, the discovery and application of N-Fmoc-N'-Boc-N'-isopropyl-L-lysine underscore its significance as a versatile tool in peptide chemistry and its potential for advancing research in medicinal chemistry and biotechnology.

References

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