D-Cyclobutylglycine is a non-proteinogenic amino acid derivative featuring a glycine backbone substituted with a cyclobutyl side chain, giving it a bulky, conformationally constrained aliphatic functionality. The molecule contains a free amino group and a free carboxyl group, with stereochemistry specified as the D-form at the alpha carbon, and it bears a hydrophobic cyclobutyl moiety that can influence steric and conformational preferences in peptide frameworks. In research and synthesis, D-cyclobutylglycine is used as a defined building block for incorporating a cyclobutyl-bearing residue into peptides and peptide analogues to support structure-activity studies, conformational probing, and chemical biology investigations of backbone and side-chain effects.
CAT No: CP20902
D-Cyclobutylglycine is a D-configured amino acid featuring a cyclobutyl-substituted side chain attached to the glycine backbone, creating a conformationally constrained, chiral amino acid intermediate for stereodefined synthesis. The molecule contains a primary amino functionality and a carboxylic acid, which together support standard amino acid derivatization and peptide coupling chemistry after appropriate protection and activation. The cyclobutyl ring contributes increased steric rigidity and hydrophobic character relative to acyclic glycine analogs, which can influence amide formation, conformational preferences, and downstream incorporation into peptide and peptidomimetic scaffolds. D-Cyclobutylglycine can be carried through protected amino acid strategies or converted into activated derivatives for controlled side-chain and backbone transformations in chemical synthesis and biochemical research workflows.
1. Peptide Synthesis
D-Cyclobutylglycine is applied in peptide synthesis as a D-amino acid building block for constructing stereochemically defined peptide bonds and peptidomimetic sequences. The amino acid backbone enables N-protection strategies and subsequent coupling using standard peptide coupling chemistries, while the carboxyl group supports formation of C-terminal amides or activated esters for sequential assembly. The D stereocenter and cyclobutyl side chain can be retained through protected amino acid handling, allowing incorporation into peptide analogs where conformational restriction and hydrophobic bulk are desired. Resulting D-cyclobutylglycine-containing peptides can serve as defined substrates for structure-activity relationship studies, protease stability assessments, and synthetic library generation in peptide science.
2. Peptidomimetics And SAR
D-Cyclobutylglycine is utilized in peptidomimetic and SAR studies where a constrained cyclobutyl side chain and D-configuration help tune backbone conformation and steric presentation. The amino acid functionality supports conversion into protected derivatives suitable for iterative synthesis of analog series, including N-protected forms for selective coupling and C-terminal functionalization for fragment linking. The cyclobutyl ring can participate in hydrophobic and steric interactions that are relevant to molecular recognition, enabling systematic comparison of analogs that differ by stereochemistry or side-chain topology. D-cyclobutylglycine-derived scaffolds can therefore be used to generate structure-defined series for binding studies, conformational mapping, and medicinal chemistry optimization.
3. Chiral Building Block Chemistry
D-Cyclobutylglycine functions as a chiral amino acid intermediate for asymmetric and stereocontrolled synthesis of D-configured derivatives. The presence of a single stereogenic center in the D-amino acid framework supports downstream stereochemical integrity during protection, activation, and coupling steps, which is critical for producing enantiopure peptide building blocks and chiral intermediates. The cyclobutyl substituent provides a rigid, non-aromatic hydrophobic motif that can be carried through synthetic sequences to yield cyclobutylglycine-containing chiral products, including protected amino acid esters and activated carboxyl derivatives. The resulting intermediates can be employed in fine chemical synthesis and stereodefined library production where D-amino acid stereochemistry must be maintained.
4. Side-Chain Functionalization
D-Cyclobutylglycine is suitable for side-chain and backbone derivatization strategies that generate functionalized amino acid derivatives for chemical biology and material-related research. The cyclobutyl-bearing side chain can be leveraged as a hydrophobic handle while the amino and carboxyl groups enable orthogonal protection patterns for selective transformations, such as N-functionalization or conversion to amide-linked conjugates. The amino acid's bifunctional nature supports formation of protected intermediates that can undergo controlled deprotection to reveal reactive groups for subsequent coupling to probes, linkers, or polymerizable units. D-cyclobutylglycine-derived conjugates can then be used to build labeled peptides, linker-defined biomolecule constructs, or synthetic scaffolds where steric rigidity and hydrophobic character influence molecular assembly.
5. Pharmaceutical Intermediate Preparation
D-Cyclobutylglycine is employed as a process-relevant pharmaceutical intermediate in the synthesis of D-amino acid-containing fragments and peptidomimetic building blocks. The carboxylic acid and amino groups enable conversion into protected amino acid derivatives and activated forms that can be integrated into stepwise manufacturing routes for peptide-like intermediates. The conformationally constrained cyclobutyl motif can be incorporated into higher-complexity intermediates used for downstream medicinal chemistry programs, including fragment coupling and late-stage amide formation. D-cyclobutylglycine thus supports industrial fine chemical synthesis workflows that require stereochemically defined amino acid inputs and robust functional group compatibility for controlled scale-up chemistry.
6. Analytical Research Standards
D-Cyclobutylglycine is applicable in analytical research as a stereochemically defined reference material and derivatization substrate for amino acid profiling and method development. The D-configuration and cyclobutyl side chain provide a distinct chemical signature that can be tracked in chromatographic and mass spectrometric workflows after conversion to detectable derivatives, including protected or activated analogs used for calibration. The amino acid's functional groups allow formation of standardized derivatives that can improve reproducibility in analytical studies targeting D-amino acid incorporation, peptide hydrolysis products, or stereochemical integrity of peptide building blocks. D-cyclobutylglycine-based analytical standards can therefore support quality control of synthetic intermediates and characterization of peptide and peptidomimetic reaction mixtures in biochemical research settings.
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