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D-Isovaline is the D enantiomer of isovaline, chemically identified as (2R)-2-amino-2-methylbutanoic acid. It is a free, nonproteinogenic α,α-disubstituted amino acid with methyl and ethyl substituents at the α-carbon.
The absence of an α-hydrogen makes isovaline structurally different from standard amino acids and can influence backbone conformational preferences. The free amino and carboxyl groups also make this material a useful precursor to Boc-, Fmoc-, ester-, or other protected derivatives.
Product Information
| Product Name | D-Isovaline |
| Chemical Name | D-Isovaline ((2R)-2-amino-2-methylbutanoic acid) |
| Catalog No. | AS2124 |
| CAS No. | 3059-97-0 |
| Molecular Formula | C5H11NO2 |
| Molecular Weight | 117.15 g/mol |
| Compound Type | Free α,α-disubstituted D-amino acid |
| Primary Research Use | Noncanonical amino-acid research, stereochemical design, and protected-derivative synthesis |
Stereochemistry and α,α-Disubstitution
The D configuration should be confirmed when a project uses isovaline as part of a stereochemical scan or as a defined non-natural residue. α,α-Disubstitution adds steric bulk near the backbone and can alter both coupling behavior and local peptide structure.
Researchers designing mirror-image or protease-resistant sequences can compare additional D-amino acid options.
Free Amino Acid Versus Protected Derivatives
D-Isovaline is supplied with both the amino and carboxyl groups available. This is useful for salt formation, derivatization, analytical standards, and preparation of route-specific protected intermediates.
For direct peptide assembly, an N-protected derivative is often operationally more convenient. The free amino acid is best selected when the desired protection state will be introduced in-house or when the unprotected molecule itself is required.
Procurement Identity
CAS 3059-97-0 and the (2R) designation provide the clearest identity anchors. This matters because isovaline, D-isovaline, L-isovaline, and protected isovaline derivatives share closely related names but are not interchangeable.
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
What is the stereochemistry of D-Isovaline?
D-Isovaline is the (2R) enantiomer for the identity associated with CAS 3059-97-0.
Is D-Isovaline proteinogenic?
No. Isovaline is a nonproteinogenic α,α-disubstituted amino acid.
Can the free amino acid be used directly in Fmoc-SPPS?
A protected derivative is usually preferred for controlled Fmoc-SPPS; the free amino acid is commonly used as a precursor or for other synthetic/analytical work.