Boc-D-Isovaline is the Boc-protected D enantiomer of isovaline, a nonproteinogenic α,α-disubstituted amino acid bearing methyl and ethyl substituents at the α-carbon. The Boc group protects the amino function while the carboxyl group remains available for activation.

The α-substitution increases steric demand around the amino-acid center and can restrict accessible backbone conformations. This makes D-isovaline derivatives useful when a project is deliberately testing conformational constraint rather than simply replacing one natural side chain with another.

Product Information

Why D-Isovaline Is Structurally Distinct

Unlike standard α-amino acids that carry an α-hydrogen, isovaline has two carbon substituents at the α-center. That substitution can influence turn/helix preferences and can change coupling kinetics because the carboxyl-bearing center is more hindered.

For a broader view of this design space, see how noncanonical residues are used to tune peptide properties.

Boc Protection and Coupling Planning

Boc protects the amino group under many coupling conditions and is removed under acidic deprotection. The free carboxyl group can be activated for solution-phase coupling or conversion into another building-block format.

Because α,α-disubstituted residues are sterically demanding, coupling conditions should be optimized for the neighboring residues and the complete sequence rather than copied from a standard amino acid.

When to Select the D Enantiomer

The D configuration is useful for stereochemical scans, protease-resistance studies, and peptidomimetic design where the D residue is intentional. Researchers comparing other mirror-image building blocks can browse D-form building blocks.

Product Documents

MSDS - Boc-D-Isovaline (AS2140)

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 makes isovaline noncanonical?

Isovaline is an α,α-disubstituted amino acid with methyl and ethyl substituents at the α-carbon and is not one of the 20 standard proteinogenic amino acids.

Is Boc-D-Isovaline sterically hindered?

Yes. α,α-Disubstitution increases steric demand and may require more deliberate coupling optimization.

What does Boc protect?

Boc protects the amino group; the carboxyl group remains available for synthetic activation.

Research Use Only.