C20-Glu-AEEA-AEEA-OSU

C20-Glu-AEEA-AEEA-OSU is a synthetic glutamic acid derivative used for peptide or protein modification. It contains a glutamic acid core acylated at the alpha-amino group with a lipophilic C20 (eicosanyl) fatty acid chain. Two AEEA units form a hydrophilic, PEG-like spacer linked to the glutamic acid side chain carboxyl group, with the terminal group of the second AEEA activated as an OSU (N-hydroxysuccinimide) ester reactive toward primary amines. Unlike tert-butyl-protected analogs, this compound lacks protecting groups and is ready for conjugation without deprotection. It enhances membrane anchoring, solubility, and bioavailability of conjugated biomolecules.

Appearance

• White to off-white solid, potentially waxy due to long alkyl chain

Source

• Chemically synthesized, not naturally occurring

• Available from specialized suppliers of modified amino acids, PEGylation, and bioconjugation reagents

Molecular Weight

• Estimated between 700–900 g/mol (lower than tBu-protected analogues)

Structure

• Eicosanyl (C20) fatty acid attached to alpha-amino group of glutamic acid via amide bond

• Glutamic acid core

• Two AEEA units linked sequentially via amide bonds to glutamic acid side chain

• Terminal OSU ester at C-terminus of second AEEA unit

Biological Activity

• Biologically inert as isolated molecule

• Activity depends on conjugated partners

• C20 chain anchors to lipid membranes

• AEEA spacer improves solubility and reduces steric hindrance

• OSU ester enables stable covalent conjugation to primary amines

Purity and Microbial Contamination

Shelf Life and Storage

• Shelf life likely shorter due to OSU ester sensitivity; typically 6–12 months

• Store at -20°C or below in dry, inert atmosphere (argon or nitrogen)

• Protect from moisture and light due to hydrolysis susceptibility

Applications

• Protein and peptide modification to add lipid anchors & PEG-like spacers

• Enhancing membrane affinity and bioavailability of conjugated molecules

• PEGylation for improved solubility and circulation

• General bioconjugation reagent targeting primary amines

• Drug delivery applications requiring membrane targeting

Key Characteristics

• Lipophilic C20 fatty acid provides membrane anchoring

• Hydrophilic AEEA spacer gives PEG-like properties

• Reactive OSU ester enables conjugation without deprotection

• Free of protective groups to allow direct use

• Balances hydrophobic and hydrophilic components for advanced biomaterials

Citation 

• Search “C20 fatty acid protein modification” or “lipid modification protein conjugation”

• Look up “PEGylation protein conjugation” or “AEEA protein modification”

• Explore “OSU ester protein conjugation” or “NHS ester protein modification” literature

• Consult supplier technical notes and chemical databases like Reaxys, SciFinder

• Review lipopeptide synthesis research

• Use keywords like “C20 protein modification,” “AEEA OSU conjugation,” “glutamic acid bioconjugation” on Google Scholar