Palm-glu(nhs)-otbu
[CAS# 204521-63-1]

Identification

• Classification: Pharmaceutical intermediate >> API intermediate
• Name: Palm-glu(nhs)-otbu
• Synonyms: 1-O-tert-butyl 5-O-(2,5-dioxopyrrolidin-1-yl) (2S)-2-(hexadecanoylamino)pentanedioate
• Molecular Formula: C₂₉H₅₀N₂O₇
• Molecular Weight: 538.72
• Protein Sequence: X
• CAS Registry Number: 204521-63-1
• EC Number: 846-837-2
• SMILES: CCCCCCCCCCCCCCCC(=O)N[C@@H](CCC(=O)ON1C(=O)CCC1=O)C(=O)OC(C)(C)C

Properties

• Solubility: Insoluble (5.1E^-4 g/L) (25 °C), Calc.^*
• Density: 1.08±0.1 g/cm³ (20 °C 760 Torr), Calc.^*
• Index of Refraction: 1.501, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2015 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362

Discovery and Applications

Palm-glu(nhs)-otbu is a chemically modified derivative of glutamic acid that plays a significant role in peptide chemistry and bioconjugation applications. Its discovery is linked to the need for developing advanced peptide-based therapeutics and drug delivery systems, particularly focusing on the incorporation of lipophilic components to enhance cellular uptake and bioactivity.

The compound features a palmitic acid moiety attached to the glutamic acid backbone through an NHS (N-hydroxysuccinimide) ester, which provides a reactive site for conjugation with amines in biomolecules. The "otbu" portion refers to a tert-butyl protective group on the carboxylate of the glutamic acid, offering stability and control during synthetic processes. The palmitic acid component serves to increase the lipophilicity of the resulting peptides, improving membrane permeability and cellular uptake.

The applications of palm-glu(nhs)-otbu are primarily found in the field of drug development and delivery systems. By linking this compound to various peptides or proteins, researchers can create modified entities with enhanced pharmacokinetic properties. The ability to introduce lipophilic chains, like palmitic acid, facilitates the delivery of therapeutic peptides across biological membranes, making them more effective in targeting specific cells or tissues.

In addition to its use in drug delivery, palm-glu(nhs)-otbu is also utilized in the design of targeted therapeutics that can interact with specific receptors or proteins within the body. This selective targeting is crucial for improving the efficacy of treatments while minimizing side effects. The NHS group allows for straightforward conjugation reactions with primary amines, making it a valuable tool in the development of novel peptide-based drugs and therapeutic agents.

Overall, palm-glu(nhs)-otbu exemplifies the advancements in peptide chemistry aimed at enhancing the performance of therapeutic agents. Its discovery and applications underscore the importance of chemical modifications in developing innovative solutions for drug delivery and targeting.

References

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