(S)-16-((1-carboxy-5-(4-((2,5-dioxopyrrolidin-1-yl)oxy)-4-oxobutanamido)pentyl)amino)-16-oxohexadecanoic acid [L-HO-Pal-Lys(OSu)-OH]

(S)-16-((1-carboxy-5-(4-((2,5-dioxopyrrolidin-1-yl)oxy)-4-oxobutanamido)pentyl)amino)-16-oxohexadecanoic acid (abbreviated as L-HO-Pal-Lys(OSu)-OH) is a synthetic building block primarily used for lipidating peptides, proteins, or other molecules. It combines palmitic acid with lysine and succinic acid activated as an N-hydroxysuccinimide (NHS) ester (OSu). The long alkyl chain imparts lipophilicity, enabling membrane insertion, while the reactive NHS ester facilitates conjugation to primary amines. Applications include membrane-anchored peptide synthesis, liposomal drug delivery, and protein modification to enhance lipophilicity or membrane interaction.

Appearance

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

Source

• Synthetically produced via chemical synthesis.

• Available from specialized chemical and bioconjugation reagent suppliers.

Molecular Weight and Structure

• Molecular Weight: Approximately 695.9 g/mol (C36H61N3O10), depending on synthesis and purification.

• Structure: Palmitic acid with a hydroxyl group at the omega carbon; lysine core; succinic acid linked to lysine’s epsilon-amino group as an active NHS ester.

Biological Activity

• Biologically inert alone; activity depends on incorporation into larger molecules.

• Long alkyl chain mediates membrane insertion, influencing localization and activity of conjugates.

• NHS ester enables conjugation to biomolecules with primary amines.

Purity and Microbial Contamination

• Purity: Typically ≥ 95% by HPLC analysis.

• Microbial Contamination: Minimal or absent, with COAs verifying microbial quality.

• Tested by bacterial endotoxin (LAL assay) and sterility assays.

Identity and Quality Control

• Mass Spectrometry (MS) confirms molecular weight.

• Nuclear Magnetic Resonance (NMR) (¹H and ¹³C) confirms chemical structure.

• Infrared (IR) spectroscopy confirms characteristic functional groups.

• HPLC to assess purity.

• Amine quantification assays verify NHS ester presence and reactivity.

Shelf Life and Storage

Application

• Lipopeptide synthesis for membrane anchorage.

• Protein lipidation to modulate membrane affinity.

• Components of liposomal formulations for drug delivery enhancements.

• Surface modification via hydrophobic coatings.

• General bioconjugation reagent targeting primary amines.

Key Characteristics

• Highly lipophilic palmitic acid chain for membrane interaction.

• Reactive NHS ester for efficient conjugation chemistry.

• Hydroxyl group offers additional functionalization options.

• Soluble in organic solvents like chloroform, dichloromethane, and DMSO.

• Versatile for synthetic conjugation applications.

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