Cbz-D-2,4-Diaminobutyric Acid: Properties & Lab Use Guide
Cbz-D-2,4-Diaminobutyric Acid: Properties & Lab Use Guide
Cbz-D-2,4-Diaminobutyric acid is a Cbz (benzyloxycarbonyl)-protected derivative of the non-proteinogenic D-configured 2,4-diaminobutyric acid, widely employed as a chiral building block in solid-phase and solution-phase peptide synthesis.
- Full Chemical Name
- N2-Cbz-D-2,4-Diaminobutyric acid (alpha-amino group free, gamma-amino group Cbz-protected, or vice versa depending on regiochemistry; confirm with certificate of analysis)
- SKU / Catalog Number
- C194710
- Protecting Group
- Cbz (benzyloxycarbonyl), removable by catalytic hydrogenolysis (H2/Pd-C) or HBr/AcOH
- Stereochemistry
- D-configuration at the alpha carbon
- Primary Application
- Chiral building block for peptide synthesis; precursor to antimicrobial and bioactive peptides
- Storage Recommendation
- Store in a cool, dry place, typically 2–8 °C or as specified on product label; protect from moisture
What Is Cbz-D-2,4-Diaminobutyric Acid?
Cbz-D-2,4-Diaminobutyric acid (DAB) is a non-proteinogenic amino acid derivative bearing two amine functionalities: one at the alpha (α) position and one at the gamma (γ, or 4-) position of the four-carbon backbone. The Cbz (benzyloxycarbonyl) group selectively protects one of these amines, allowing the other to participate in coupling reactions during peptide assembly.
The D-configuration distinguishes this compound from its natural L-counterpart, conferring resistance to many proteolytic enzymes and enabling the synthesis of D-amino acid-containing peptides with enhanced metabolic stability. The compound is catalogued under SKU C194710 at Aladdin Scientific and is supplied for research-grade applications.
Key Physical and Chemical Properties
Cbz-D-2,4-Diaminobutyric acid is a solid at room temperature. Key physicochemical characteristics include:
- Molecular formula: C12H16N2O4 (free-acid form; verify exact formula and molecular weight on the product certificate of analysis, as regiochemistry of Cbz placement affects the structure).
- Protecting group stability: The Cbz group is stable under basic conditions and to many nucleophiles, but is cleaved by catalytic hydrogenolysis (Pd/C, H2) or strong acid (HBr in acetic acid). This orthogonality is exploited in multi-step synthesis.
- Solubility: Generally soluble in polar aprotic solvents (DMF, DMSO) and partially in methanol or ethanol; limited solubility in water at neutral pH. Verify specific solubility data on the CoA.
- Optical activity: Exhibits specific optical rotation consistent with D-configuration; exact value should be confirmed from the product CoA.
All specific numerical values (MW, mp, optical rotation) should be verified against the certificate of analysis supplied with SKU C194710.
Applications in Peptide Synthesis and Research
The primary utility of Cbz-D-2,4-Diaminobutyric acid lies in peptide chemistry and medicinal chemistry research:
- Solid-phase peptide synthesis (SPPS): Used as a Cbz-protected building block where selective deprotection of the alpha-amine enables sequential chain elongation while the side-chain amine remains masked.
- Antimicrobial peptide analogs: 2,4-Diaminobutyric acid (DAB) residues are found in natural antimicrobial peptides such as polymyxins. Synthetic analogs containing D-DAB residues are explored for improved proteolytic stability.
- Peptidomimetics and D-peptide libraries: Incorporation of D-amino acids into peptide libraries increases resistance to proteolysis, a key feature in drug discovery programs.
- Branched peptide and dendrimer synthesis: The bifunctional amine scaffold of DAB allows construction of branched or dendritic peptide architectures.
Researchers are advised to consult primary literature and optimize coupling conditions (reagents, solvent, temperature) for their specific synthetic targets.
Handling, Storage, and Safety
As with all fine chemical reagents, proper handling and storage of Cbz-D-2,4-Diaminobutyric acid (C194710) are essential to maintain product integrity and ensure laboratory safety:
- Storage: Store at 2–8 °C (or as indicated on the product label) in a tightly sealed container, protected from light and moisture. Long-term storage under inert atmosphere (argon or nitrogen) is recommended if the container will be opened repeatedly.
- Handling: Use appropriate personal protective equipment (PPE) including lab coat, gloves, and eye protection. Work in a well-ventilated area or fume hood when weighing the compound.
- Stability: The Cbz group is susceptible to hydrogenolysis; avoid prolonged exposure to hydrogen gas, palladium catalysts, or strong protic acids during storage.
- Disposal: Follow institutional and local regulatory guidelines for disposal of amino acid derivatives and organic chemicals.
Always consult the Safety Data Sheet (SDS) for C194710 before use. Contact Aladdin Scientific technical support for SDS access or handling queries.
Ordering, Purity, and Quality Assurance
Aladdin Scientific supplies Cbz-D-2,4-Diaminobutyric acid under SKU C194710. Key quality and procurement considerations include:
- Purity: Research-grade purity is standard; the exact purity specification (e.g., ≥95% or ≥98% by HPLC) is stated on the product page and certificate of analysis. Contact our sales team to confirm current lot purity before placing a large order.
- Available pack sizes: Multiple pack sizes may be available to support both small-scale feasibility studies and larger synthetic campaigns. Check the product listing for current availability.
- Certificate of Analysis (CoA): A lot-specific CoA including identity (NMR or MS), purity (HPLC), and optical rotation data is available upon request or via the Aladdin website.
- Custom quantities: For bulk or custom requirements, contact Aladdin Scientific customer service to discuss pricing, lead times, and availability.
- Shipping: The compound is shipped under conditions appropriate for its stability. Cold-chain shipping may apply; verify at checkout or with customer service.
Frequently asked questions
What is the difference between Cbz-D-2,4-Diaminobutyric acid and Cbz-L-2,4-Diaminobutyric acid?
The two compounds are enantiomers differing only in the stereochemical configuration at the alpha carbon: the D-form has the opposite spatial arrangement of substituents compared to the naturally occurring L-form. This difference profoundly affects biological activity, proteolytic stability, and application in asymmetric synthesis. D-configured residues are incorporated into peptides to resist enzymatic degradation and to explore non-natural chemical space.
How is the Cbz protecting group removed from Cbz-D-2,4-Diaminobutyric acid?
The Cbz (benzyloxycarbonyl) group is most commonly removed by catalytic hydrogenolysis using hydrogen gas and a palladium catalyst (e.g., 10% Pd/C in methanol or ethanol). Alternatively, treatment with HBr in acetic acid or trifluoroacetic acid in the presence of appropriate scavengers can be used. The choice of deprotection method should be compatible with other functional groups and protecting groups present in the molecule.
What solvents are recommended for dissolving Cbz-D-2,4-Diaminobutyric acid?
Cbz-D-2,4-Diaminobutyric acid is generally soluble in polar aprotic solvents such as DMF and DMSO, and may dissolve partially in alcohols such as methanol and ethanol. Solubility in water is typically limited at neutral pH but may improve under acidic or basic conditions. Always prepare a test solution with a small quantity before scaling up, and verify specific solubility data on the certificate of analysis for lot C194710.
Is Cbz-D-2,4-Diaminobutyric acid suitable for GMP or clinical use?
The product supplied under SKU C194710 is intended for research use only and is not certified for GMP, pharmaceutical, veterinary, or clinical diagnostic applications. Researchers requiring material for regulated applications should contact Aladdin Scientific to discuss whether appropriate grades or custom synthesis services are available.
How should I store Cbz-D-2,4-Diaminobutyric acid to maximize shelf life?
Store the compound at 2–8 °C in a tightly sealed, moisture-proof container, away from light and incompatible materials such as strong oxidizers or reducing agents. For frequently accessed stocks, consider aliquoting into smaller portions to minimize repeated exposure to ambient conditions. Always check the expiry date and lot-specific CoA for any changes in appearance or purity before use.
References
- Bodanszky, M. & Bodanszky, A. The Practice of Peptide Synthesis. Springer, 1994. (General reference for Cbz protecting group chemistry in peptide synthesis.)
- Merrifield, R. B. Solid phase peptide synthesis. J. Am. Chem. Soc. 1963, 85, 2149–2154. (Foundational reference for SPPS methodology relevant to building block use.) doi:10.1021/ja00897a025
- Velkov, T. et al. Structure-activity relationships of polymyxin antibiotics. J. Med. Chem. 2010, 53, 1898–1916. (Contextual reference for diaminobutyric acid residues in antimicrobial peptides.) doi:10.1021/jm900999h
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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