Myristoyl-Gly-OH is an acylated amino acid derivative in which glycine bears a myristoyl (tetradecanoyl) group attached to the amino functionality, forming an amide while retaining a free carboxylic acid (-COOH) at the glycine terminus. The molecule therefore contains an amide linkage between the myristoyl acyl chain and the glycine nitrogen, along with the characteristic glycine carboxyl group, and its long C14 hydrophobic side chain provides a nonpolar surface for membrane-associated or amphiphilic behavior in chemical systems. Myristoyl-Gly-OH is used in peptide and conjugate chemistry as a building block or substrate-like intermediate for preparing acylated glycine derivatives, studying lipid-peptide or lipid-surface interactions, and generating hydrophobic handles for bioconjugation and analytical method development.
Myristoyl-Gly-OH is an N-myristoyl glycine derivative in which a long-chain C14 saturated fatty acyl group is attached to the glycine nitrogen, while the molecule retains a free carboxylic acid at the glycine C-terminus. The amphiphilic structure combines a hydrophobic myristoyl tail with a polar, ionizable carboxylate, enabling membrane-associated behavior and controlled solubility across pH ranges. The single stereocenter of glycine is absent, simplifying stereochemical handling while focusing reactivity on the amide (acylated amine) and the acid functionality. The compound behaves as a chemically defined lipidated amino acid building block suitable for peptide coupling, linker installation, and downstream derivatization in chemical biology and industrial synthetic workflows.
1. Lipidated Peptide Synthesis
Myristoyl-Gly-OH supports lipidated peptide and peptidomimetic construction by providing a myristoyl-protected N-terminus equivalent alongside a free carboxylic acid for coupling chemistry. The N-myristoyl amide is stable under common peptide coupling conditions, while the terminal carboxyl group can be activated to form amide bonds with amino components, enabling incorporation of a lipidated glycine unit at the growing peptide chain. The hydrophobic tail can influence aggregation and solubility during synthesis and purification, making the building block relevant for designing peptide fragments that model lipid-dependent interactions. Myristoyl-Gly-OH can be used to generate longer acylated sequences and to prepare defined lipid-amino acid intermediates for subsequent assembly into larger biomolecular constructs.
2. Chemical Biology Probes
Myristoyl-Gly-OH is applicable in chemical biology for constructing membrane-interacting probes and for studying lipid-mediated recognition using defined acylated amino acid motifs. The myristoyl group serves as a hydrophobic anchor, while the free carboxyl group enables conjugation to amine-bearing targets, solid supports, or heterobifunctional linkers used in probe development. The amide linkage preserves the lipid headgroup geometry, supporting reproducible presentation of the acyl chain in assays that depend on hydrophobic contacts. Myristoyl-Gly-OH can be employed as a starting material for labeled or immobilized lipidated glycine analogs used in interaction mapping, pull-down reagent preparation, and molecular recognition studies.
3. Bioconjugation Linkers
Myristoyl-Gly-OH functions as a lipid-bearing conjugation handle in bioconjugation workflows where a carboxyl-activated glycine unit is needed to connect hydrophobic motifs to biomolecules. The terminal carboxylic acid can be transformed into activated esters or coupling-ready derivatives to form stable amide bonds with lysine-rich proteins, peptide tags, or amino-functional polymers, while the N-myristoyl amide maintains the hydrophobic character of the conjugate. The amphiphilic balance can affect conjugate partitioning and surface presentation, which is relevant for generating acylated biomolecule conjugates used in labeling strategies and reagent fabrication. Myristoyl-Gly-OH therefore serves as a practical intermediate for producing lipidated conjugates and for preparing defined lipid-functional biomaterials.
4. Process Chemistry Intermediate
Myristoyl-Gly-OH is suitable for process chemistry intermediate preparation in fine chemical and specialty chemical manufacturing where controlled lipid-amino acid derivatives are required. The molecule contains a single reactive acid site suitable for conversion into coupling intermediates, while the N-myristoyl amide provides chemical robustness across typical activation and coupling steps. The long-chain fatty acyl group enables downstream formation of higher-order lipidated building blocks, including protected or activated variants for stepwise assembly in manufacturing routes. Myristoyl-Gly-OH can be used as a reproducible feedstock for producing lipidated amino acid reagents used in peptide synthesis, conjugation reagent manufacture, and industrial synthesis of amphiphilic intermediates.
5. Analytical Standards And Assay Reagents
Myristoyl-Gly-OH can be employed in analytical research as a reference standard and calibration component for lipidated glycine derivatives and acylated peptide fragments. The defined myristoyl chain combined with a free carboxylic acid provides a characteristic mass and chromatographic behavior that supports method development for LC-MS or related analytical platforms targeting N-acyl glycine motifs. The compound can also serve as a model substrate or control reagent in assays that evaluate acyl transfer chemistry or lipid-dependent processing steps in vitro. Myristoyl-Gly-OH thus supports quantitative characterization of lipidated amino acid species and enables consistent interpretation of analytical data during synthetic and biochemical investigations.
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