D-Cyclobutylalanine is a non-proteinogenic amino acid derivative featuring a cyclobutyl-substituted side chain attached to the alpha carbon, classifying it as an aliphatic amino acid analog used in peptide and structure-activity studies. The molecule contains a free amino group and a free carboxyl group on the alpha position and is specified in the D stereochemical form, with the cyclobutyl ring providing a conformationally constrained hydrophobic functionality. In synthesis, D-Cyclobutylalanine can be employed as a substrate or building block for incorporating a cyclic side-chain motif into peptide analogs or for developing labeled and chemically defined amino acid derivatives used in binding studies and analytical method development.
CAT No: CP20802
D-Cyclobutylalanine is a D-stereochemical amino acid featuring a cyclobutyl-substituted side chain attached to the α-carbon, providing a conformationally constrained hydrophobic motif that can influence peptide backbone/side-chain packing. The molecule contains a primary amino group and a carboxylic acid functionality, enabling standard amino acid coupling chemistry and salt formation, while the non-aromatic cyclobutyl group contributes distinct steric and lipophilicity characteristics relative to linear alkyl alanine derivatives. As a chiral amino acid building block, D-Cyclobutylalanine participates in stereochemically controlled peptide bond formation and can serve as a chiral intermediate for downstream derivatization. The side-chain cyclobutane ring can also be leveraged for structure-property studies, including conformational effects on peptidomimetics and enzyme recognition.
1. Peptide Synthesis
D-Cyclobutylalanine is applied in peptide synthesis as a D-configured amino acid building block for assembling stereochemically defined sequences and for introducing a cyclobutyl side chain into peptide backbones. The presence of the α-amino and α-carboxyl groups supports peptide coupling after appropriate temporary protection of the amine and activation of the acid, enabling compatibility with common protected amino acid strategies used in solid-phase or solution-phase assembly. The cyclobutyl side chain can be incorporated to probe how constrained hydrophobic bulk affects folding, protease susceptibility, and conformational preferences of peptide analogs. Downstream peptide products can be further elaborated into peptidomimetics and research-grade standards for biochemical assays and structure-activity relationship studies.
2. Peptidomimetics Design
D-Cyclobutylalanine is used in peptidomimetics and molecular design workflows where side-chain sterics and conformational restriction are targeted to modulate molecular recognition. The cyclobutyl group, attached at the amino acid side chain position, enables systematic variation of hydrophobic surface area and steric profile while retaining an amino acid-derived stereocenter. The α-amino acid scaffold supports conversion into N-protected derivatives for iterative fragment coupling, allowing construction of analog libraries with controlled D-configuration at the residue. Resulting cyclobutyl-bearing peptide analogs can then be employed in structure-activity relationship studies and biochemical characterization of binding-site tolerance to stereochemical and steric changes.
3. Chemical Biology Probes
D-Cyclobutylalanine is suitable for chemical biology research where amino acid incorporation is used to generate probes for studying biomolecular interactions and enzyme substrate preferences. The amino acid functional groups can be transformed into protected intermediates that enable site-specific incorporation into peptides used as recognition elements in pull-downs, competition assays, or mechanistic studies. The D-configuration and cyclobutyl side chain can help tune resistance to proteolysis and alter noncovalent interactions, supporting investigation of how constrained hydrophobic residues influence binding and catalysis. Downstream derivatives can be used as analytical substrates or reference materials for monitoring reaction pathways and for mapping structure-function relationships in peptide-based systems.
4. Protected Amino Acid Chemistry
D-Cyclobutylalanine is employed as a chiral starting material for protected amino acid synthesis and for manufacturing-ready intermediate preparation used in peptide building block pipelines. The free amino and carboxyl groups enable conversion into N-protected amino acid derivatives and, where needed, carboxyl-activated forms or ester intermediates that support controlled coupling chemistry. The stereogenic α-carbon allows retention of D-configuration through protection/deprotection sequences, which is critical for producing stereochemically consistent peptide fragments. Cyclobutyl side-chain integrity supports downstream functional transformations on the backbone-derived intermediates, enabling scalable production of defined amino acid reagents for fine chemical synthesis.
5. Process Chemistry Intermediate
D-Cyclobutylalanine is applicable as a chiral amino acid intermediate in process chemistry for producing stereodefined building blocks used in industrial peptide and specialty chemical manufacturing. The stable amino acid core can be routed through protection, activation, and purification steps that align with manufacturing workflows for protected amino acids and peptide coupling reagents. The cyclobutyl side chain provides a distinct hydrophobic motif that can be carried through multi-step syntheses without requiring aromatic functional-group handling, simplifying downstream derivatization logic. Resulting intermediates can feed into larger-scale syntheses of cyclobutyl-containing peptide analogs, chiral fragments for combinatorial chemistry, and biochemical research components requiring consistent stereochemical identity.
6. Analytical Research Standards
D-Cyclobutylalanine is utilized in analytical research as a stereochemically defined reference material for method development and compound identification in amino acid and peptide analysis. The D-configuration and cyclobutyl side chain create a characteristic chromatographic and mass-spectral signature that can support LC-MS/MS method validation for peptide hydrolysates, amino acid profiling, and stereochemical verification workflows. The compound's functional groups enable derivatization strategies commonly used for amino acid detection, including conversion to protected or derivatized forms compatible with analytical instrumentation. Downstream use includes calibration standards for quantitative assays of amino acid composition and for confirming incorporation of cyclobutyl-bearing residues in synthesized peptide materials.
2. Store-operated Ca2+ entry sustains the fertilization Ca2+ signal in pig eggs
5. Immune responses to homocitrulline-and citrulline-containing peptides in rheumatoid arthritis
If you have any peptide synthesis requirement in mind, please do not hesitate to contact us at . We will endeavor to provide highly satisfying products and services.
Creative Peptides is a trusted CDMO partner specializing in high-quality peptide synthesis, conjugation, and manufacturing under strict cGMP compliance. With advanced technology platforms and a team of experienced scientists, we deliver tailored peptide solutions to support drug discovery, clinical development, and cosmetic innovation worldwide.
From custom peptide synthesis to complex peptide-drug conjugates, we provide flexible, end-to-end services designed to accelerate timelines and ensure regulatory excellence. Our commitment to quality, reliability, and innovation has made us a preferred partner across the pharmaceutical, biotechnology, and personal care industries.
Read More