ALLOC-L-LYS(BOC)-OH DCHA is a protected lysine derivative in which the α-amino acid framework is modified to bear an ALLOC group and a Boc-protected ε-amino side chain, corresponding to an L-lysine stereochemical configuration at the α-carbon as indicated by the "L-LYS" designation. The molecule contains a free carboxylic acid group (-COOH) while the ε-amino functionality is masked as a tert-butoxycarbonyl (Boc) carbamate and the α-amino functionality is protected as an allyloxycarbonyl (ALLOC) carbamate, with DCHA indicating association with dicyclohexylamine as a counterion for the salt form. In peptide synthesis workflows, this protected amino acid is employed as a stepwise coupling building block where orthogonal amino protection enables controlled deprotection and subsequent formation of amide bonds for the assembly of lysine-containing peptide structures or peptide-related intermediates.
CAT No: CP01411
CAS No:110637-53-1
Synonyms/Alias:N-α-Allyloxycarbonyl-N-ε-Boc-Llysinedicyclohexylaminesalt;
ALOC-L-LYS(BOC)-OH DCHA is a protected L-lysine derivative that incorporates an ALLOC (allyloxycarbonyl) group on the ε-amino side chain together with a BOC (tert-butoxycarbonyl) protecting group on the α-amino functionality, while retaining the carboxylic acid as a free acid. The lysine backbone provides a stereogenic α-center in the L-configuration and a second functional handle at the ε-position, enabling orthogonal protection and selective deprotection sequences during peptide assembly. The presence of the DCHA counterion is consistent with a salt-form amino acid intermediate, which can influence solubility and handling in peptide synthesis and downstream derivatization operations. The combination of orthogonally removable protecting groups supports controlled peptide coupling chemistry, side-chain functionalization, and preparation of lysine-based fragments for synthetic and biochemical research workflows.
1. Orthogonal Peptide Building Blocks
ALOC-L-LYS(BOC)-OH DCHA is used in peptide synthesis workflows requiring orthogonal lysine protection, where the ALLOC group on the ε-amino side chain can be removed independently from the BOC-protected α-amino group. The α-carboxylic acid and BOC-protected α-amino functionality support standard peptide coupling chemistry after activation of the acid, while the orthogonal ALLOC handle enables selective exposure of the lysine ε-amine for subsequent chain extension or side-chain modification. Orthogonality supports stepwise construction of protected peptide segments, including lysine-containing sequences where controlled chemoselectivity is needed to avoid premature side-chain reactions. Lysine-derived fragments prepared from this amino acid intermediate can be carried into longer peptide analog construction and can also serve as a defined input for automated peptide assembly strategies.
2. Side-Chain Functionalization Chemistry
ALOC-L-LYS(BOC)-OH DCHA is applicable to chemical biology and bioconjugation chemistry focused on lysine side-chain derivatization, leveraging the ε-amino group revealed after ALLOC deprotection. The protected lysine architecture provides a protected α-amino/acid motif for controlled peptide or linker installation, while the ε-amine enables attachment of functional moieties such as amide-forming groups, activated esters, or nucleophile-reactive handles used in downstream labeling and molecular modification. The DCHA salt form can support practical handling during synthesis steps that involve intermediate isolation or salt-controlled solubility adjustments. Resulting lysine-functionalized intermediates can be converted into peptide conjugates, affinity probes, or scaffold components for structure-activity relationship studies and molecular recognition investigations.
3. Protected Amino Acid Synthesis
ALOC-L-LYS(BOC)-OH DCHA is suitable for process chemistry intermediate preparation where orthogonally protected amino acids are required as reproducible inputs to downstream peptide building blocks. The BOC-protected α-amino group and ALLOC-protected ε-amino group provide a defined protection pattern that can be carried through activation of the carboxylic acid and subsequent coupling steps without uncontrolled side reactions. The free carboxylic acid functionality supports conversion to activated derivatives used in peptide coupling chemistry, enabling manufacturing-route design for lysine-containing intermediates. Salt-associated properties from the DCHA counterion can be leveraged to improve workflow compatibility in fine chemical synthesis operations that depend on consistent material handling and intermediate stability.
4. Peptidomimetics And SAR Studies
ALOC-L-LYS(BOC)-OH DCHA supports peptidomimetic and SAR studies by enabling controlled incorporation of lysine stereochemistry and side-chain functionality into peptide-like scaffolds. The L-configuration at the α-center and the protected amine pattern allow assembly of lysine-containing analogs where ε-amine reactivity can be tuned through orthogonal deprotection and subsequent derivatization. The carboxylic acid and protected amine groups enable systematic generation of analog series through stepwise coupling and side-chain modification, supporting fragment-based exploration of structure-function relationships in synthetic libraries. Downstream products derived from this intermediate can include lysine-modified peptide analogs, constrained peptidomimetics, and defined chemical probes used to map binding or recognition features.
5. Analytical Standards For Lysine Derivatives
ALOC-L-LYS(BOC)-OH DCHA can be employed in analytical research as a reference material for monitoring protected lysine chemistry, including verification of protection states and deprotection selectivity. The presence of two distinct protecting groups (BOC and ALLOC) together with the free carboxylic acid provides characteristic analytical signatures that can assist in method development for peptide synthesis QC, such as LC-based separation of protection-state isomers or salt-form intermediates. The DCHA counterion contributes to reproducible material behavior in sample preparation, which can be relevant for consistent analytical comparisons across synthesis batches. Lysine derivative standards prepared from this compound can be used to support identity confirmation, impurity profiling, and method validation for peptide coupling and protecting-group transformation steps.
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