D-Vinylglycine is a non-proteinogenic amino acid featuring a vinyl-substituted side chain attached to the α-amino acid backbone, placing it in the amino acid class used for chemical biology and peptide chemistry. The molecule contains an amino group and a carboxyl group on the α-carbon while the side chain bears a carbon-carbon double bond, and the "D-" designation indicates the stereochemical form at the α-carbon. D-Vinylglycine is employed as a building block in the synthesis of modified peptides and as a substrate analogue in enzyme-substrate studies or analytical method development where an alkene-containing amino acid side chain provides a defined chemical handle for further derivatization.
CAT No: CP09603
D-Vinylglycine is a D-configured amino acid derivative featuring an amino acid backbone bearing a vinyl side chain, which functions as an unsaturated, stereochemically defined handle for chemical transformation. The molecule contains a primary amino functionality and a carboxylic acid (or its salt/derivatized forms depending on handling), enabling salt formation and controlled protection for peptide-coupling compatible chemistry. The vinyl group participates in addition, cycloaddition, and selective functionalization reactions, while the D-stereocenter supports stereochemically consistent incorporation into amino acid-based scaffolds. As a chiral amino acid intermediate and amino acid analog, D-Vinylglycine can be converted into protected derivatives and downstream functionalized building blocks for synthetic and biochemical research.
1. Enzyme Inhibitor Studies
D-Vinylglycine is used in chemical biology and enzyme studies where amino acid analogs with reactive side chains help probe catalytic mechanisms and substrate recognition. The D-amino acid stereochemistry and the vinyl side chain can be leveraged to generate covalent or affinity-based probes after appropriate derivatization, while the carboxyl and amino functionalities support formation of salts, protected intermediates, and binding-mimetic analogs. Vinyl functionalization strategies enable access to electrophilic or constrained variants that can be evaluated as mechanistic tools in inhibitor design workflows. Downstream derivative formation from D-Vinylglycine supports the preparation of structure-activity relationship (SAR) libraries and mechanistic reference compounds for biochemical assays.
2. Peptidomimetic Construction
D-Vinylglycine is applied in peptidomimetic and unnatural amino acid scaffold synthesis where incorporation of a vinyl-bearing D-amino acid can tune conformation and reactivity. The amino acid backbone enables standard peptide coupling chemistry when the amine and acid are appropriately protected or activated, and the vinyl side chain can be retained for post-coupling modification or converted into substituted side chains. Stereochemical control from the D-configuration supports consistent geometry in peptide analogs and can influence binding-site interactions in receptor or enzyme systems. Vinyl-to-functional group transformations downstream enable access to cyclized, substituted, or crosslinkable peptidomimetics for mapping pharmacophores and optimizing molecular recognition.
3. Protected Amino Acid Derivatives
D-Vinylglycine is suitable for protected amino acid synthesis workflows that require orthogonal protection of the amino and carboxyl groups for stepwise assembly. The primary amine and carboxylic acid can be converted into N-protected, acid-activated, or esterified forms that participate in peptide coupling or sequential derivatization without uncontrolled side reactions. The vinyl group can be preserved under compatible protection schemes or selectively transformed under conditions tailored to the unsaturation, supporting iterative synthesis of chiral intermediates. Process-oriented preparation of protected D-Vinylglycine derivatives supports fine chemical production of peptide building blocks, chiral intermediates, and research-grade amino acid analogs.
4. Side-Chain Functionalization
D-Vinylglycine is employed in synthetic organic chemistry and industrial intermediate preparation where the vinyl moiety serves as a reactive synthetic handle for downstream functional group installation. The unsaturated side chain can undergo addition, oxidation, or cycloaddition-type transformations to generate substituted amino acid derivatives that retain the D-stereocenter and amino acid connectivity. The presence of amino acid functionality enables conversion into N-protected intermediates that can be carried through multi-step sequences, including formation of amide, ester, or activated acid derivatives for subsequent coupling. Resulting functionalized products can feed into combinatorial chemistry, heterocycle construction from amino acid precursors, and manufacturing routes that require chiral, stereodefined building blocks.
5. Analytical Standards And Labeling
D-Vinylglycine is used in analytical research and method development where amino acid analogs provide reference material for chromatographic separation, derivatization studies, and stereochemical verification strategies. The D-configuration and vinyl side chain support the preparation of defined derivatives for LC-MS/MS method calibration and for monitoring derivatization efficiency in amino acid workflows. Vinyl-bearing structures can also be adapted to labeling or tagging chemistries after functionalization to introduce detectable groups while maintaining the amino acid backbone for consistent analytical behavior. Analytical-grade derivative preparation from D-Vinylglycine supports quality control of synthetic intermediates and supports interpretation of peptide coupling or modification outcomes in research laboratories and specialty chemical production.
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