1-Benzyl 5-(2,5-dioxopyrrolidin-1-yl) palmitoyl-L-glutamate
[CAS# 294855-89-3]

Identification

• Classification: Biochemical >> Common amino acids and protein drugs
• Name: 1-Benzyl 5-(2,5-dioxopyrrolidin-1-yl) palmitoyl-L-glutamate
• Synonyms: 1-O-benzyl 5-O-(2,5-dioxopyrrolidin-1-yl) (2S)-2-(hexadecanoylamino)pentanedioate
• Molecular Formula: C₃₂H₄₈N₂O₇
• Molecular Weight: 572.73
• Protein Sequence: X
• CAS Registry Number: 294855-89-3
• SMILES: CCCCCCCCCCCCCCCC(=O)N[C@@H](CCC(=O)ON1C(=O)CCC1=O)C(=O)OCC2=CC=CC=C2

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.589, Calc.^*
• Boiling Point: 789.3±60.0 °C (760 mmHg), Calc.^*
• Flash Point: 431.2±32.9 °C, Calc.^*

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

Discovery and Applications

1-Benzyl 5-(2,5-dioxopyrrolidin-1-yl) palmitoyl-L-glutamate is a synthetic chemical compound primarily used in biochemical and pharmaceutical research. It belongs to the class of modified amino acid derivatives that are designed to aid in the conjugation of lipid molecules to peptides or proteins. The compound features a palmitoyl group attached to an L-glutamate backbone, with the benzyl and dioxopyrrolidinyl moieties providing selective reactivity and stability during chemical reactions.

The discovery of such compounds is tied to the growing interest in lipidation, a process where lipid groups are attached to peptides or proteins to enhance their biological properties. Lipidation plays a critical role in improving the bioavailability, membrane permeability, and overall pharmacokinetics of biomolecules. This has been particularly useful in drug design, where the attachment of fatty acids like palmitoyl to peptide drugs increases their stability and efficacy in vivo.

In terms of synthesis, the introduction of the 2,5-dioxopyrrolidinyl group, or succinimide, into 1-benzyl 5-palmitoyl-L-glutamate facilitates the formation of stable amide bonds with nucleophilic groups like amines, which are commonly found in peptides or proteins. This property allows for efficient conjugation under mild conditions, making it useful in the synthesis of lipidated peptides or protein-lipid conjugates. The palmitoylation of peptides, a process facilitated by compounds like this, is a method commonly used to improve drug delivery by increasing hydrophobicity, which in turn enhances interactions with cell membranes.

Applications of 1-benzyl 5-(2,5-dioxopyrrolidin-1-yl) palmitoyl-L-glutamate can be found in the development of therapeutic agents, particularly in the field of targeted drug delivery and vaccine development. Palmitoylated peptides are more likely to associate with lipid bilayers and cellular membranes, improving their cellular uptake and the overall delivery of therapeutic molecules. This compound’s design is ideal for creating lipid-modified peptides that have a longer half-life and better interaction with biological membranes, enhancing their therapeutic potential.

Another significant application is in the field of immunology, where lipidated peptides are often used to increase the immunogenicity of peptide-based vaccines. The lipophilic properties imparted by the palmitoyl group allow the modified peptides to associate more effectively with immune cells, potentially improving the immune response generated by the vaccine. This has broad implications for developing vaccines against various diseases, including cancers and viral infections.

Ongoing research into lipidated peptide conjugates continues to explore new ways to harness the benefits of lipidation for improved drug design. The versatility and efficiency of 1-benzyl 5-(2,5-dioxopyrrolidin-1-yl) palmitoyl-L-glutamate in attaching lipid moieties to peptides or proteins make it a valuable tool in this evolving field, particularly in efforts to design more effective therapeutic agents and vaccines.

References

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