(S)-2-(15-carboxy-pentadecanoylamino)-pentanedioic acid 5-(2,5-dioxo-pyrrolidin-1-yl) ester [L-HO-Pal-Glu(OSu)-OH]

(S)-2-(15-carboxy-pentadecanoylamino)-pentanedioic acid 5-(2,5-dioxo-pyrrolidin-1-yl) ester (L-HO-Pal-Glu(OSu)-OH) is a synthetic building block used for lipidating peptides and proteins. It combines hydroxylated palmitic acid (HO-Pal) with glutamic acid activated as an N-hydroxysuccinimide (NHS) ester (OSu). The hydrophobic HO-Pal moiety embeds into lipid membranes, while the NHS ester reacts with primary amines on biomolecules for conjugation. The hydroxyl group on palmitic acid allows further modification or crosslinking.

Appearance

• White to off-white solid, potentially waxy.

Source

• Chemically synthesized, not naturally occurring.

• Available from specialized chemical suppliers.

Molecular Weight and Structure

• Approximate molecular weight: 612.7 g/mol (C29H50N2O10).

• Structure includes hydroxylated palmitic acid linked to glutamic acid with NHS activation of side chain.

Biological Activity

• Biologically inert alone.

• Activity depends on conjugated molecules.

• Enables membrane insertion and covalent conjugation for bioconjugation.

Purity and Microbial Contamination

• Purity: ≥ 95% by HPLC.

• Minimal microbial contamination verified by bacterial endotoxin (LAL) and sterility tests.

Identity and Quality Control

• Confirmed by MS, NMR, IR spectroscopy.

• Purity assessed by HPLC.

• NHS ester reactivity confirmed by amine quantification.

Shelf Life and Storage

Applications

• Lipopeptide synthesis for membrane anchoring.

• Protein lipidation to enhance membrane binding.

• Liposomal drug delivery formulations.

• Surface modification with hydrophobic coatings.

• Bioconjugation reagent for covalent coupling to amines.

Key Characteristics

• Lipophilic hydroxylated palmitic acid enables membrane interaction.

• Highly reactive NHS ester facilitates conjugation.

• Versatile for chemical synthesis and subsequent modification via hydroxyl.

• Soluble in chloroform, dichloromethane, DMSO.

Citation 

• Search “NHS ester lipid protein conjugation” or “OSu ester lipid protein conjugation.”

• Look for “hydroxylated palmitic acid synthesis” or “modification.”

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

• Articles on “liposomal drug delivery” and “NHS ester lipid.”

• Supplier catalogs and technical data sheets.

• Use chemical databases like Reaxys, SciFinder, PubChem, ChemSpider.

• Google Scholar keywords: “L-HO-Pal-Glu(OSu)-OH,” “lipid NHS ester conjugation,” “hydroxylated palmitic acid lipidation,” “liposomal formulation NHS ester.”

• Consider “click chemistry lipid-protein conjugation” for alternative conjugation methods.