(S)-5-(tert-butoxy)-5-oxo-4-palmitamidopentanoic acid [L-Pal-Glu(OH)-OtBu]

(S)-5-(tert-butoxy)-5-oxo-4-palmitamidopentanoic acid (L-Pal-Glu(OH)-OtBu) is a synthetic building block used for incorporating a lipid anchor and a protected glutamic acid residue into peptides or proteins. It contains palmitic acid linked via an amide bond to the alpha-amino group of glutamic acid, with the alpha carboxyl group protected as a tert-butyl ester (OtBu) and the gamma carboxyl group free (OH). This structure facilitates membrane affinity and provides a modifiable site for further conjugation.

Appearance

• White to off-white solid, potentially waxy due to palmitic acid.

Source

• Synthetic chemical production.

• Available from specialized lipid chemistry and bioconjugation suppliers.

Molecular Weight and Structure

• Approximate molecular weight: 485.7 g/mol (C25H47NO6).

• Structure: Palmitic acid attached to glutamic acid alpha-amino group via amide bond; glutamic acid alpha-carboxyl tert-butyl protected; free gamma carboxyl.

Biological Activity

• Inert alone; biological function depends on conjugated molecules.

• Palmitic acid moiety promotes membrane association.

• Free carboxyl group offers conjugation or electrostatic interaction potential.

Purity and Microbial Contamination

• Typically ≥ 95% purity by HPLC.

• Minimal microbial contamination; COAs include microbial tests.

• Tested by bacterial endotoxin and sterility assays.

Identity and Quality Control

• Confirmed by MS, NMR (¹H and ¹³C), IR spectroscopy.

• Purity evaluated by HPLC.

• Acid value determination for free carboxyl quantification.

Shelf Life and Storage

Applications

• Lipopeptide synthesis with membrane anchoring.

• Protein lipidation to enhance membrane affinity.

• Liposomal formulations incorporating palmitoylated peptides.

• Surface modification with hydrophobic coatings.

• Drug delivery via amphiphilic conjugates.

Key Characteristics

• Lipophilicity from palmitic acid allows membrane insertion.

• Hydrophilic glutamic acid residue with modifiable free carboxyl group.

• Acid-labile tert-butyl protection allows controlled deprotection.

• Soluble in chloroform, dichloromethane, and DMSO.

Citation

• Search “palmitic acid protein modification” or “lipopeptide synthesis.”

• Use “glutamic acid tert-butyl ester synthesis” or “modification.”

• Search for “amino acid lipid conjugate synthesis.”

• Articles on “liposomal drug delivery palmitoylated peptides.”

• Studies on “self-assembling peptides lipid modification.”

• Supplier datasheets and technical notes.

• Use Reaxys, SciFinder, PubChem databases.

• Google Scholar keywords: “palmitic acid protein modification,” “glutamic acid tert-butyl ester,” “liposomal drug delivery palmitoylated peptide,” “self-assembling peptide lipid.”