DL-Vinylglycine is a non-proteinogenic amino acid analogue featuring a vinyl substituent on the side chain and a glycine-like backbone with an amino group and a carboxyl group. The molecule exists as a DL stereochemical mixture as indicated by the "DL" designation and bears the free amino and carboxylic acid functionalities, enabling formation of amino acid derivatives such as salts, esters, or protected intermediates for controlled reactivity. DL-Vinylglycine is used in peptide-chemistry and chemical biology workflows where vinyl-bearing amino acid analogues provide a handle for incorporation into synthetic sequences or for subsequent derivatization and labeling studies.
CAT No: CP09601
DL-Vinylglycine is a DL mixture of an amino acid analog featuring a vinyl-substituted side chain that behaves as an unsaturated, nucleophile-bearing functional group while retaining an amino and carboxylate motif typical of amino acid chemistry. The compound's stereochemical descriptor "DL" indicates racemic configuration at the alpha carbon, which influences coupling stereoselectivity and the composition of downstream peptide or peptidomimetic products. Vinylglycine's side chain can participate in electrophile addition and controlled derivatization, while its amino and carboxyl functions can be protected or activated for peptide coupling chemistry. As a chiral and functionalized amino acid intermediate, DL-Vinylglycine supports synthetic routes that convert the amino acid framework into protected building blocks, labeled derivatives, or reactive peptidomimetic scaffolds for biochemical research and industrial fine chemical synthesis.
1. Peptide Synthesis
DL-Vinylglycine is applied in peptide synthesis and peptidomimetic construction where an amino acid-like backbone is required alongside a side chain bearing a vinyl handle for post-coupling modification. The amino and carboxyl functionalities can be protected as N-protected amino acid derivatives and activated as coupling partners to enable amide bond formation under standard peptide coupling conditions. The racemic DL stereochemistry can be leveraged when preparing libraries of vinyl-containing analogs for structure-activity relationship studies or when stereochemical purity is not the primary design constraint. Downstream, vinylglycine-containing peptides and peptide fragments can undergo further functionalization through addition or derivatization of the alkene, supporting iterative scaffold elaboration in synthetic organic chemistry and biochemical research.
2. Enzyme Studies
DL-Vinylglycine is used in chemical biology and enzyme studies as an amino acid analog that introduces an unsaturated side chain capable of engaging enzyme active sites through substrate-mimetic binding modes. The presence of the amino acid core enables incorporation into inhibitor-like or substrate-like constructs, including N-terminal or side-chain-modified variants that can be assembled via peptide coupling chemistry. The vinyl functionality can serve as a reactive moiety for mechanistic probes or for designing analogs that undergo controlled transformations during assay workflows. Research-grade derivatives prepared from DL-Vinylglycine can feed into inhibitor characterization, mechanism-of-action investigations, and comparative studies of enzyme recognition of unsaturated amino acid motifs.
3. Amino Acid Derivatization
DL-Vinylglycine supports amino acid derivatization workflows where the vinyl side chain acts as a functional handle for downstream transformations beyond standard protected amino acid chemistry. The compound's amino and carboxyl groups enable formation of protected intermediates, such as N-protected derivatives and ester or activated acid forms, which can be selectively deprotected or reactivated to match synthetic sequence requirements. Vinylglycine's alkene can be converted into substituted side chains through addition chemistry, enabling access to substituted amino acid analogs, crosslinkable reagents, or reactive intermediates for polymer and materials chemistry. Industrially relevant fine chemical synthesis routes can employ DL-Vinylglycine-derived building blocks as controlled-chemistry intermediates for producing functionalized amino acid derivatives at scale.
4. Peptidomimetics And SAR
DL-Vinylglycine is incorporated into peptidomimetic and SAR studies where the amino acid framework provides compatibility with peptide-like scaffolds while the vinyl substituent enables chemical diversification after assembly. The racemic DL configuration provides a practical entry point for generating stereochemically mixed analog sets, which can be useful for mapping binding tolerance to stereochemistry and side-chain electronics during medicinal chemistry optimization. The ability to protect and activate the amino acid functions supports iterative synthesis of analog series, including N-terminal modifications, C-terminal activation, and side-chain functionalization strategies. Resulting vinyl-containing peptidomimetics can be further elaborated into analogs bearing substituted side chains, supporting fragment-based molecular design and structure-guided refinement of amino acid-derived pharmacophores.
5. Polymer And Materials Modification
DL-Vinylglycine is suitable for functional materials and polymer modification applications where the vinyl group enables incorporation into reactive networks or post-modification chemistry while the amino acid core supports conjugation strategies. The amino and carboxyl functionalities can be converted into protected or activated derivatives that participate in coupling to surfaces, linkers, or polymer backbones, enabling formation of amino acid-derived functional units. Vinylglycine-derived intermediates may be used to generate alkene-bearing linkers that can undergo subsequent addition reactions to install desired functional groups for material performance tuning. This amino acid analog chemistry aligns with industrial specialty chemical production needs for controllable functional monomers, crosslinkable building blocks, and downstream derivatized materials intermediates.
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