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Z-Aib-OH is Cbz-protected 2-aminoisobutyric acid (Aib), an α,α-disubstituted amino acid widely used as a conformationally restrictive residue in peptide and peptidomimetic chemistry. The amino group is protected with Cbz, while the carboxyl group remains available for coupling.
Aib is achiral because its α-carbon carries two identical methyl groups. Its value comes from backbone steric effects rather than D/L stereochemistry, making it a useful probe for helicity, turns, and proteolytic stability in designed sequences.
Product Information
| Product Name | Z-Aib-OH |
| Chemical Name | N-Cbz-2-aminoisobutyric acid (Cbz-Aib-OH) |
| Catalog No. | AS2025 |
| CAS No. | 15030-72-5 |
| Molecular Formula | C12H15NO4 |
| Molecular Weight | 237.25 g/mol |
| Compound Type | Cbz-protected α-aminoisobutyric acid |
| Primary Research Use | Conformationally constrained Aib building block for peptide and solution-phase synthesis |
Aib as a Conformationally Restricted Residue
Aib lacks an α-hydrogen and introduces substantial steric substitution near the peptide backbone. It is frequently used to bias local conformational preferences and can support helical structure in appropriate sequence contexts.
These design principles are part of the broader use of noncanonical amino acids in peptide optimization.
Why Use Cbz Protection?
The Z/Cbz group is useful in solution-phase or mixed protecting-group strategies where Fmoc is not preferred. The free carboxyl group allows activation for coupling to another amino or peptide component.
Deprotection conditions should be chosen for the full molecule because Cbz removal, side-chain protections, and other reducible groups can interact with route design.
Coupling Considerations
Aib is sterically demanding. Coupling efficiency depends strongly on the neighboring residue and activation method, and difficult sequences may require more aggressive or repeated activation than standard amino acids.
Product Documents
The Safety Data Sheet provides product identification, hazard information, handling and storage guidance, exposure controls, transport information, and regulatory information for laboratory use.
Certificates of Analysis (COAs) are batch-specific. Please contact us to request the COA for your product, and we will provide it by email.
Frequently Asked Questions
Is Aib chiral?
No. 2-Aminoisobutyric acid has two identical methyl groups at the α-carbon and is achiral.
Why is Aib used in peptide design?
Its α,α-disubstitution can restrict backbone conformation and is often used to investigate helicity, turns, and proteolytic stability.
What does Z mean in Z-Aib-OH?
Z is another abbreviation for the Cbz amino protecting group.