L-Vinylglycine is a naturally occurring amino acid analogue featuring the amino acid backbone with a vinyl substituent on the side chain, placing it in the class of non-proteinogenic, alkenyl-containing amino acids. The molecule bears a free amino group and a carboxyl group consistent with an amino acid functionality, and its side chain contains an alkene that can participate in stereospecific or addition-type chemical transformations while remaining distinct from the canonical side-chain chemistries of proteinogenic residues. L-Vinylglycine is used in peptide chemistry and chemical biology as a substrate or building block for preparing modified peptides and amino acid derivatives, where the reactive vinyl handle supports structure-activity studies, conjugation strategies, or analytical method development involving chemically defined amino acid analogues.
CAT No: CP09602
L-Vinylglycine is an L-amino acid derivative featuring a stereogenic center at the alpha-carbon and a vinyl-substituted side chain that can participate in electrophilic addition, radical chemistry, and controlled polymerization-type transformations. The molecule contains the amino acid functional motif (primary amine and carboxylic acid), with the free acid/amine pairing enabling salt formation and compatibility with standard amino acid coupling and derivatization logic. The unsaturated side chain provides a handle distinct from typical aliphatic or aromatic amino acids, enabling downstream conversion to functionalized analogs through hydrofunctionalization, cycloaddition, or oxidative modification. As a chiral amino acid intermediate, L-Vinylglycine can be incorporated into synthetic sequences that require stereochemical fidelity while introducing a reactive carbon-carbon double bond for further functional group elaboration.
1. Enzyme Inhibitor Research
L-Vinylglycine is applied in chemical biology and enzyme studies where amino acid-like recognition is combined with a side-chain that can undergo addition chemistry to generate reactive or binding-relevant motifs. The L-configuration at the alpha-carbon supports stereospecific substrate binding models, while the vinyl group can be leveraged to create mechanism-based analogs or to probe active-site tolerance for unsaturation. Carboxylic acid and amino functionality enable preparation of N-protected or salt forms that can be used in inhibitor screening libraries and structure-activity relationship studies. Downstream derivatization can generate analogs with modified side-chain length, oxidation state, or heteroatom substitution, supporting iterative medicinal chemistry and biochemical interrogation of catalytic residues.
2. Peptide Analog Synthesis
L-Vinylglycine is utilized as a chiral building block for peptide synthesis and peptidomimetic construction where the vinyl side chain replaces a saturated methylene pattern to tune conformation and reactivity. The amino acid backbone supports standard peptide coupling chemistry after appropriate protection of the amine and activation of the carboxyl group, enabling incorporation at internal positions or as a terminal residue for C-terminal modification strategies. The vinyl functionality can be retained through peptide assembly and then converted post-coupling to introduce additional functional groups, enabling access to vinyl-derived crosslinkers, cyclized scaffolds, or side-chain substituted analogs. Resulting peptide analogs can be used to map binding determinants, evaluate protease processing susceptibility, and generate chemically defined substrates for biochemical assays.
3. Chemical Biology Labeling
L-Vinylglycine is suitable for biomolecule modification workflows in which an amino acid-derived handle is required for chemoselective functionalization. The vinyl group can participate in addition-based conjugation strategies, while the amino acid framework allows conversion into protected derivatives that improve solubility control and coupling compatibility with carrier proteins or targeting ligands. Carboxyl and amine groups support formation of activated esters or amide linkers after derivatization, enabling attachment to peptides, small-molecule probes, or polymer backbones. Vinylglycine-derived conjugates can serve as analytical reagents or mechanistic probes that connect stereochemical recognition elements with a reactive side-chain for downstream functional group installation.
4. Process Chemistry Intermediate
L-Vinylglycine is employed in process chemistry and fine chemical synthesis as a chiral amino acid intermediate bearing an unsaturated side chain that can be converted into multiple downstream building blocks. The L-stereocenter provides a stereochemically defined feedstock for manufacturing routes that require retention or controlled transformation of chirality during derivatization. The vinyl group can be used as a controlled-reactivity handle for subsequent steps such as hydrofunctionalization, oxidative conversion to carbonyl-containing derivatives, or incorporation into heterocycle-forming sequences. The presence of amino acid functionality facilitates salt management, protection/deprotection planning, and integration into scalable synthetic logic for producing vinyl-functionalized intermediates and specialty chemical precursors.
5. Polymer and Materials Functionalization
L-Vinylglycine is applied in functional materials and polymer modification contexts where an amino acid-derived monomeric or comonomer-like unit can introduce reactive unsaturation into macromolecular structures. The vinyl side chain enables incorporation into polymer architectures through addition or radical-mediated growth concepts, while the amino acid functionality can be transformed into protected or neutral forms to control reactivity during polymer processing. Carboxylic acid groups can be used for post-functionalization, enabling ion-pairing, surface anchoring, or conversion to amide/ester linkages for material property tuning. Vinylglycine-derived polymers or small-molecule crosslinkers can then be used to generate chemically defined coatings, functional hydrogels, or amino acid-based materials that retain stereochemical origin for structure-dependent behavior.
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