Nα-Palmitoyl-(L)-glutamic acid-γ-succinimidyl ester[L-Pal-Glu(OSu)-OH]

Nα-Palmitoyl-(L)-glutamic acid-γ-succinimidyl ester (L-Pal-Glu(OSu)-OH) is a synthetic building block used to lipidate peptides, proteins, or other molecules. It combines palmitic acid (a saturated fatty acid) linked to L-glutamic acid, with the gamma carboxyl activated as an N-hydroxysuccinimide (NHS) ester (OSu), enabling conjugation to primary amines. The alpha carboxyl remains free for additional modifications. The lipophilic palmitic acid facilitates membrane insertion, while the reactive NHS ester allows covalent modifications.

Appearance

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

Source

• Synthetic; available from specialized chemical and bioconjugation vendors.

Molecular Weight and Structure

• Molecular Weight: Approx. 510.6 g/mol (C25H42N2O8).

• Structure: Palmitic acid attached to alpha-amino of L-glutamic acid; free alpha carboxyl; gamma carboxyl activated as NHS ester.

Biological Activity

• Inert as standalone; activity depends on conjugated structure.

• Promotes membrane localization via palmitic acid.

• NHS ester reacts with primary amines; free alpha carboxyl allows further modification.

Purity and Microbial Contamination

• Purity: Typically ≥ 95% (HPLC).

• Minimal microbial contamination; COAs with endotoxin and sterility testing provided.

Identity and Quality Control

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

• Purity checked by HPLC; optical rotation confirms L-configuration.

• Amine quantification verifies NHS ester activity; acid value verifies free carboxyl.

Shelf Life and Storage

Applications

• Lipopeptide synthesis with membrane anchoring.

• Protein lipidation to enhance membrane interaction.

• Liposomal drug delivery formulations.

• Surface modification with hydrophobic functionalization.

• General bioconjugation reagent for primary amines.

Key Characteristics

• Lipophilic palmitoyl chain for membrane insertion.

• Reactive NHS ester for conjugation to amines.

• Free alpha carboxyl allows further functionalization.

• Soluble in chloroform, dichloromethane, DMSO.

Citation

• NHS ester lipid conjugation chemistry and bioconjugation applications:
  https://pubmed.ncbi.nlm.nih.gov/30613757/

• Palmitoylation and lipid modification of peptides and proteins:
  https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6653962/

• Applications of NHS esters in bioconjugation and drug delivery:
  https://pubmed.ncbi.nlm.nih.gov/20420327/

• Liposomal drug delivery using lipid conjugates with NHS esters:
  https://pubmed.ncbi.nlm.nih.gov/30817167/

• Self-assembling lipopeptides with membrane anchoring lipid moieties:
  https://pubmed.ncbi.nlm.nih.gov/29395641/

• Chemical databases for lipidated glutamate and palmitic acid conjugates:
  https://pubchem.ncbi.nlm.nih.gov/compound/5386443

• Reviews on protein lipidation and fatty acylation in therapeutic design:
  https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5357263/

• Patents related to lipid-protein conjugates and drug delivery formulations:
  https://patents.google.com/patent/US20170268536A1/en

• Bioconjugation techniques using NHS esters for site-specific protein modification:
  https://pubmed.ncbi.nlm.nih.gov/29454358/

• Fatty acylation mechanisms and their biological implications:
  https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7167378/