Boc-D-Lys(Z)-OH is a protected amino acid derivative of D-lysine bearing an N-terminal Boc (tert-butoxycarbonyl) protecting group and a side-chain Z (benzyloxycarbonyl) protecting group on the ε-amino functionality. The molecule contains both an α-amino group and a carboxylic acid (as the free acid) while the two protected amines are masked as carbamates, controlling chemoselectivity by reducing undesired nucleophilic side reactions during stepwise peptide assembly. It is used as a protected lysine building block in peptide synthesis workflows, where orthogonal protection of the α- and ε-amino groups supports selective deprotection and coupling strategies for preparing lysine-containing peptides and related amino acid derivatives.
CAT No: CP27209
CAS No:55878-47-2
Synonyms/Alias:55844-94-5;SCHEMBL8792149;AKOS025395562;AK173991
Boc-D-Lys(Z)-OH is a protected D-lysine building block bearing a Boc group on the alpha-amino functionality and a benzyloxycarbonyl (Z) protecting group on the side-chain epsilon-amino group. This orthogonally protected lysine derivative is commonly used to introduce a D-lysine residue into peptide sequences while maintaining side-chain protection during assembly. The presence of two robust protecting groups supports controlled stepwise peptide synthesis and downstream deprotection strategies that are compatible with standard peptide chemistry workflows.
1. D-Lysine Peptide Synthesis
Boc-D-Lys(Z)-OH is used by peptide synthesis groups to incorporate a D-lysine residue into both research peptides and peptide-based materials where stereodefined lysine placement is required. The Boc protection on the alpha-amino group enables sequential coupling under Boc-compatible peptide assembly conditions, while the Z group on the side-chain prevents undesired side reactions from the lysine epsilon-amine during chain elongation. This makes the reagent particularly useful for generating D-lysine-containing segments in peptide libraries, structure-activity relationship (SAR) studies, and stereochemical control experiments where the D-configuration is a key design element.
2. Side-Chain Protected Lysine Building Block
Boc-D-Lys(Z)-OH serves as a practical lysine unit for workflows that require the epsilon-amino group to remain masked until a planned deprotection step. In custom peptide manufacturing and medicinal chemistry research, the protected side chain helps maintain sequence integrity during multi-step synthesis and reduces the risk of branching or cross-coupling from free lysine functionality. Researchers commonly select this specific protection pattern when they want to defer lysine side-chain functionalization (for example, later conversion to a reactive handle or incorporation into a defined post-synthetic modification strategy) while still assembling the peptide backbone with high fidelity.
3. Stereocontrolled Peptidomimetic Development
Boc-D-Lys(Z)-OH is frequently chosen in peptidomimetic and peptide conjugate development programs that rely on D-amino acid incorporation to tune peptide conformation and sequence stereochemistry. Medicinal chemistry and chemical biology teams use D-lysine-containing peptides as defined stereochemical probes in binding and interaction studies, as well as as scaffolds for studying how lysine positioning influences structure and reactivity. The dual protection strategy supports reliable assembly of these stereochemically defined motifs, enabling downstream steps that depend on selective unveiling of the lysine side chain at a controlled stage of the development workflow.
4. Pharmaceutical Intermediate Segment Synthesis
Boc-D-Lys(Z)-OH is also applied as a protected amino acid intermediate for preparing lysine-containing peptide segments used in downstream pharmaceutical intermediate development. Process chemistry and peptide intermediate suppliers often rely on stable, well-defined protected building blocks to reduce variability across synthesis batches and to support reproducible segment coupling. In this context, Boc-D-Lys(Z)-OH provides a protected lysine unit that can be carried through intermediate stages without premature side-chain reactivity, supporting the preparation of defined peptide fragments used for further derivatization or final assembly.
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