N-Succinimidyl myristate [Myr-OSu]

N-Succinimidyl myristate (Myr-OSu) is a reactive ester derivative of myristic acid (a 14-carbon saturated fatty acid) used mainly for acylating primary amines in proteins, peptides, lipids, and other biomolecules. The N-hydroxysuccinimide (NHS) ester group enables stable amide bond formation with primary amines under mild conditions, making it highly suitable for bioconjugation applications. The myristoyl group adds hydrophobicity, promoting membrane association and modulating protein interactions and intracellular trafficking. Applications include protein lipidation, liposome modification, and creation of self-assembling biomaterials.

Appearance

• White to off-white solid.

Source

• Chemically synthesized; not naturally occurring.

• Available from specialized chemical suppliers and bioconjugation reagent vendors.

Molecular Weight and Structure

• Approximately 367.5 g/mol (C18H31NO4).

• Structure: Myristic acid linked via ester bond to N-hydroxysuccinimide.

Biological Activity

• Biologically inert alone.

• Activity upon conjugation with biomolecules; myristoyl promotes membrane anchoring and modulates protein-protein interactions.

Purity and Microbial Contamination

• Typically ≥ 95% purity by HPLC.

• Minimal microbial contamination; COA includes microbial tests.

• Tested with bacterial endotoxin (LAL assay) and sterility assessments.

Identity and Quality Control

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

• Purity measured by HPLC; amine reactivity confirmed by quantification assays.

Shelf Life and Storage

Applications

• Protein myristoylation, adding membrane anchors.

• Peptide acylation with myristoyl groups.

• Liposomal formulation with myristoylated lipids.

• Surface hydrophobic modification.

• General bioconjugation reagent for primary amines.

Key Characteristics

• Lipophilic myristoyl group promotes membrane interaction.

• Highly reactive NHS ester for conjugation.

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

• Versatile reagent for chemical synthesis and modification.

Citation

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

• Myristoylation and its biological implications:
  https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5357263/

• N-myristoyltransferases and protein myristoylation:
  https://pubmed.ncbi.nlm.nih.gov/23020254/

• Liposomal drug delivery systems using myristoylated lipids:
  https://pubmed.ncbi.nlm.nih.gov/30817167/

• Bioconjugation approaches with NHS esters:
  https://pubmed.ncbi.nlm.nih.gov/20420327/

• Protein lipidation for membrane targeting:
  https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6653962/

• Synthesis of myristoylated peptides and lipids:
  https://doi.org/10.1021/acs.jmedchem.1c00565

• Self-assembling materials utilizing lipid modifications:
  https://pubmed.ncbi.nlm.nih.gov/29395641/

• Chemical databases for N-Succinimidyl myristate structure and properties:
  https://pubchem.ncbi.nlm.nih.gov/compound/N-succinimidyl-myristate

• Patents on protein lipidation and drug delivery platforms:
  https://patents.google.com/patent/US20170268536A1/en