N-α-Boc-N-δ-Z-D-lysine is a protected lysine derivative in which the α-amino group is carbamated with a Boc (tert-butoxycarbonyl) group and the ε-amino side chain is protected with a Z (benzyloxycarbonyl/Cbz-type) group, while the carboxyl group remains in the protected amino acid form. The molecule contains both α- and ε-amino functionalities masked as carbamates and a free carboxyl group, and its name specifies the D stereochemical configuration at the lysine α-carbon. In peptide chemistry, this orthogonally protected lysine analogue functions as a stepwise building block that can be incorporated into peptide sequences while the Boc and Z groups help control chemoselectivity during iterative coupling and deprotection steps, and it can also serve as a substrate for preparing lysine-containing peptide derivatives for structure-activity and labeling studies.
CAT No: CP01423
CAS No:76477-42-4
Synonyms/Alias:Boc-D-Lys(Z)-OH;76477-42-4;55878-47-2;N-Boc-N'-Cbz-D-lysine;BOC-N-EPSILON-Z-D-LYSINE;Boc-L-Lys(Z)-OH;AmbotzBAA1358;AC1OJJ2G;BOC-D-LYS-OH;BOC-D-LYSINE(CBZ);SCHEMBL3210903;CTK2H6952;N-A-BOC-N-D-Z-D-LYSINE;MolPort-005-938-132;N(5)-Boc-N(1)-Cbz-D-Lys;ZINC4521274;N-ALPHA-BOC-N-D-Z-D-LYSINE;KM1770;MFCD00038262;NALPHA-BOC-NGAMMA-Z-D-LYSINE;AKOS024258523;AB01718;CB-1684;CS19316;EBD2208196
N-α-Boc-N-δ-Z-D-lysine is a D-lysine derivative bearing two orthogonal protecting groups on the ε- and α-amino functions: an N-α Boc carbamate and an N-δ benzyloxycarbonyl (Z) protecting group. The molecule retains the lysine side-chain carbon skeleton and stereogenic D-configuration at the amino acid center, while the carboxyl group is present as the free acid or acid-form functionality depending on the supplied form, enabling controlled peptide coupling chemistry. The Boc and Z groups provide differential stability under common peptide synthesis conditions, allowing stepwise deprotection and selective functional group exposure. The protected diamino architecture and chiral backbone make the compound a practical chiral intermediate for constructing lysine-containing peptides, peptidomimetics, and side-chain modified analogs with predictable reactivity at the remaining functional sites.
1. Peptide Synthesis
N-α-Boc-N-δ-Z-D-lysine is applied as a protected lysine building block in peptide synthesis workflows where orthogonal N-protection is required for sequential coupling and selective deprotection. The N-α Boc group supports acid-labile removal to expose the α-amino function for amide bond formation, while the N-δ Z carbamate can be preserved during earlier steps and removed under hydrogenolysis-compatible conditions when ε-amino exposure is needed. The lysine side-chain geometry and preserved stereochemistry enable incorporation into linear peptide sequences and cyclic scaffolds where D-lysine stereocontrol affects conformational preferences and protease resistance profiles. Downstream, the compound can be used to generate protected peptide fragments that maintain compatibility with standard coupling chemistries and subsequent functionalization at the ε-position.
2. Side-Chain Functionalization
N-α-Boc-N-δ-Z-D-lysine is suitable for side-chain functionalization strategies that rely on controlled ε-amino availability after orthogonal deprotection. The ε-amino functionality is masked as the Z carbamate during early synthetic stages, preventing undesired cross-reactions during formation of the peptide backbone or installation of other protecting groups. Stepwise unmasking can enable targeted derivatization such as acylation, alkylation, or attachment of linkers for conjugation chemistry, while the D-chiral center maintains stereochemical identity in the resulting lysine-containing intermediates. The resulting ε-functionalized derivatives can serve as inputs for peptidomimetics, binding probes, and engineered amino acid analogs used in chemical biology and SAR-focused library construction.
3. Chemical Biology Labeling
N-α-Boc-N-δ-Z-D-lysine is employed in chemical biology and biomolecule modification contexts where lysine-reactive handles are introduced with stereochemical control. The orthogonally protected amines facilitate preparation of defined peptide or small-molecule conjugates in which the ε-amino group can be selectively exposed for subsequent coupling to activated esters, isothiocyanates, aldehyde-derived tags, or other electrophiles used for labeling. The D-lysine configuration can be incorporated to tune stability against enzymatic degradation and to influence binding interactions in receptor or protein interaction studies, supporting reproducible probe design. Downstream conjugates prepared from this intermediate can be used as analytical reagents, affinity reagents, or structured ligands for studying molecular recognition and interaction networks.
4. Peptidomimetics And SAR Studies
N-α-Boc-N-δ-Z-D-lysine is applied in peptidomimetic construction and structure-activity relationship studies where protected D-lysine residues are incorporated into analog scaffolds. The protected α- and ε-amino groups allow controlled assembly of amide-rich backbones and enable late-stage diversification at the ε-position without scrambling the chiral center. Orthogonal deprotection strategies support generation of libraries with systematic variation in side-chain chemistry, including altered charge density, hydrogen-bonding patterns, and steric environment around the lysine residue. The resulting D-lysine-containing analogs can be used as synthetic intermediates for SAR evaluation workflows, supporting consistent comparisons across series of peptide-like compounds.
5. Pharmaceutical Intermediate Preparation
N-α-Boc-N-δ-Z-D-lysine is relevant to pharmaceutical manufacturing and fine chemical synthesis as a chiral, protected lysine intermediate used to build defined peptide fragments and amino acid derivatives. The Boc and Z protecting groups provide a practical route for protecting-group management during scale-up, enabling sequential exposure of the α-amino and ε-amino functionalities to match the order of coupling and purification steps typical of peptide intermediate production. The chiral lysine backbone supports reproducible stereochemical outcomes in downstream API-related synthesis of peptide-based intermediates, including D-lysine incorporated sequences used for stability engineering. The compound's protected diamino structure therefore functions as a controllable input for process chemistry routes that require predictable chemoselectivity and compatibility with standard peptide coupling and deprotection operations.
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