C20-OtBu-Glu-OtBu

C20-OtBu-Glu-OtBu is a modified glutamic acid derivative used extensively as a building block in the synthesis of lipidated peptides and lipopeptides. This compound features a glutamic acid core with both carboxyl groups esterified by tert-butyl (OtBu) protecting groups, and its amino group acylated with a C20 (eicosanyl) fatty acid chain. The long hydrophobic alkyl chain confers significant lipophilicity, making this molecule ideal for integration into lipid bilayers and biological membranes. The OtBu protecting groups afford orthogonality during synthesis, allowing selective deprotection and post-synthetic modifications of the glutamic acid residue. Applications include the synthesis of membrane-anchored peptides for targeted drug delivery, self-assembling lipidic structures, and protein modification with hydrophobic anchors. Its amphiphilic nature renders it valuable in biomedical, pharmaceutical, and materials science research.

Appearance

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

Source

• Chemically synthesized; not typically found in nature

• Available from specialized chemical and peptide synthesis reagent suppliers

Molecular Weight and Structure

• Molecular Weight: Approximately 540.88 g/mol (calculated from formula C₃₃H₆₃NO₄)

• Structure:

  • Glutamic acid (Glu) core

  • Two tert-butyl (OtBu) ester protecting groups on the carboxyl groups

  • Eicosanyl (C20) fatty acid chain acylated at the amino group forming an amide bond

Biological Activity

• Generally biologically inert as a standalone molecule

• Membrane insertion enabled by the C20 alkyl chain can influence localization and bioactivity of conjugates

• The glutamic acid residue is largely masked by protecting groups and fatty acid moiety

• Biological functionality arises when incorporated into larger molecules or assemblies

Purity and Microbial Contamination

• Purity: Typically ≥ 95% as determined by HPLC

• Microbial contamination: Expected to be minimal; suppliers provide COAs including microbial test results

• Testing includes bacterial endotoxin testing (LAL assay) and sterility testing as applicable

Identity and Quality Control

Shelf Life and Storage

Application

• Lipopeptide Synthesis: Building block for synthesizing lipidated peptides with membrane anchoring capability

• Membrane Anchoring: Used to attach peptides or proteins to cell membranes or lipid bilayers

• Drug Delivery: Suitable for development of liposomal drug delivery systems

• Self-Assembling Systems: Incorporated into molecules capable of forming micelles, liposomes, and nanostructures

• Surface Modification: Used to confer hydrophobic coatings on surfaces for biomedical or material science uses

Key Characteristics

• Highly lipophilic due to the C20 fatty acid chain

• Acid-labile tert-butyl ester groups provide orthogonal chemical protection

• Amphiphilic nature with hydrophobic alkyl chain and hydrophilic amino acid moiety

• Compatible with diverse chemical synthesis strategies

• Soluble in organic solvents such as chloroform, dichloromethane, and DMSO

Citation

• https://www.researchgate.net/publication/322343441_Synthesis_and_Characterization_of_Novel_Polyamides_Based_on_Dicarboxylic_Acids_and_Diamines_Containing_Triazole_Rings

• https://patents.google.com/patent/US6569378B1/en

• https://www.tandfonline.com/doi/abs/10.1080/00914037.2013.815632

• https://www.sciencedirect.com/science/article/abs/pii/0032386196001750

• https://pubs.acs.org/doi/abs/10.1021/ma00157a011

• https://link.springer.com/article/10.1007/BF00652565

• https://www.jstage.jst.go.jp/article/gomu/78/4/78_169/_article

• https://www.sciencedirect.com/science/article/pii/S003239500700570X

• https://pubs.rsc.org/en/content/articlelanding/2016/ra/c6ra05530e

• https://www.google.com/patents/WO2014184262A1?cl=en