N-α-Boc-N-ε-allyloxycarbonyl-D-lysine dicyclohex is a protected lysine derivative in which the α-amino group is Boc-protected and the ε-amino side chain is masked as an allyloxycarbonyl (Alloc) carbamate, with the lysine backbone bearing a free carboxyl group. The molecule contains both an α-carboxylic acid and carbamate-protected amino functionalities, and the D stereochemical designation indicates the side-chain stereochemistry relative to the amino acid backbone. In peptide synthesis and related stepwise coupling workflows, the orthogonal Boc/Alloc protection pattern supports chemoselective deprotection and controlled incorporation of a lysine residue bearing a side-chain protected as an Alloc carbamate, while the dicyclohex counterion form can be used as a defined salt/solid form for handling and reagent preparation.
CAT No: CP01414
CAS No:327156-94-5
Synonyms/Alias:N-α-Boc-N-ε-allyloxycarbonyl-D-lysinedicyclohexylaminesalt;327156-94-5;BOC-D-LYS(ALOC)-OHDCHA;Boc-D-Lys(Alloc)-OH(dicyclohexylammonium)salt;BOC-D-LYS-OHDCHA;72909_ALDRICH;72909_FLUKA;ACT10789;6339AH;AKOS022181389;AK-61214;Boc-D-Lys(Alloc)-OHdicyclohexylaminesalt;Boc-D-Lys(Alloc)-OHdicyclohexylammoniumsalt;K-7589;N|A-Alloc-N|A-Boc-D-lysine(dicyclohexylammonium)salt;N|A-Boc-N|A-Alloc-D-lysine(dicyclohexylammonium)salt;Nalpha-Boc-Ndelta-Alloc-D-lysinedicyclohexylaminesalt;Ndelta-Alloc-Nalpha-Boc-D-lysinedicyclohexylaminesalt;Boc-D-Lys(Alloc)-OHinvertedexclamationmarkcurrencyDCHA;Nalpha-Boc-Ndelta-Alloc-D-lysine(dicyclohexylammonium)salt;Ndelta-Alloc-Nalpha-Boc-D-lysine(dicyclohexylammonium)salt;Dicyclohexylamine(R)-6-(((allyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)hexanoate
N-α-Boc-N-ε-allyloxycarbonyl-D-lysine dicyclohex is a D-lysine-based, orthogonally protected amino acid derivative featuring an N-terminal Boc carbamate and an ε-side-chain allyloxycarbonyl (Alloc) protecting group, together with a dicyclohex counterion or salt form that can influence handling, crystallinity, and downstream solubility. The molecule retains the lysine backbone stereochemistry at the D-configured α-carbon, while presenting a protected α-amino functionality and a protected ε-amino functionality that can be selectively unveiled under orthogonal deprotection conditions. The Boc and Alloc groups provide controlled stability during peptide coupling and allow programmed access to the free amine for subsequent derivatization, conjugation, or further protection. The presence of ester-like carbonate/ carbamate linkages and the allyl carbonate handle supports predictable functional-group transformations that are compatible with protected amino acid synthesis workflows and peptide building block preparation.
1. Protected Amino Acids
N-α-Boc-N-ε-allyloxycarbonyl-D-lysine dicyclohex is used in protected amino acid chemistry where orthogonal N- and side-chain protection is required to manage lysine reactivity during multi-step synthesis. The Boc-protected α-amino group and Alloc-protected ε-amino group enable selective deprotection strategies that can be sequenced to generate a single free amine for targeted coupling or functionalization. The D-lysine stereocenter supports stereochemically defined peptide construction and chiral building block design for unnatural amino acid incorporation. The salt or counterion form can be leveraged as a practical intermediate for downstream peptide building block preparation and controlled handling in fine chemical synthesis.
2. Peptide Synthesis
N-α-Boc-N-ε-allyloxycarbonyl-D-lysine dicyclohex serves as a lysine-containing peptide coupling component in solid-phase or solution-phase peptide synthesis workflows. The Boc group protects the α-amino functionality against premature reaction, while the Alloc group on the ε-amine allows lysine side-chain participation to be deferred until the desired stage of chain assembly. The orthogonal protecting-group set supports programmed access to the ε-amine for subsequent side-chain functionalization, including attachment of linkers, tags, or solubilizing groups without disrupting the peptide backbone. The D-configuration provides stereochemical control for generating D-lysine-containing peptide analogs used in peptide science, peptidomimetic construction, and structure-defined scaffold generation.
3. Bioconjugation Chemistry
N-α-Boc-N-ε-allyloxycarbonyl-D-lysine dicyclohex is applicable to bioconjugation chemistry where lysine-side-chain amine presentation is required for controlled coupling to biomolecular targets. The protected ε-amine can be revealed on demand to enable amide bond formation, carbamate formation, or linker installation while keeping the α-amino group protected to preserve chemoselectivity. The orthogonal Boc/Alloc strategy supports stepwise conjugation designs, including sequential attachment of functional groups for chemical biology probes, affinity handles, or immobilization surfaces. The D-lysine stereochemistry can be used in molecular design to tune stability and recognition properties of conjugated biomolecule derivatives used in downstream analytical and research workflows.
4. Side-Chain Functionalization
N-α-Boc-N-ε-allyloxycarbonyl-D-lysine dicyclohex supports side-chain functionalization programs that rely on selective unmasking of the lysine ε-amine. The Alloc protecting group provides an allyl-derived handle that can be removed without disturbing the Boc carbamate under compatible conditions, enabling controlled generation of a reactive primary amine for derivatization. The resulting free ε-amine can be used to install functional groups for molecular recognition studies, such as amide-linked motifs, urea/guanidine-like linkers, or charged substituents that modulate solubility and binding behavior. The protected lysine scaffold also serves as a chiral amino acid intermediate for building peptidomimetic fragments and for generating libraries of lysine-functionalized derivatives in synthetic organic chemistry.
5. Pharmaceutical Manufacturing
N-α-Boc-N-ε-allyloxycarbonyl-D-lysine dicyclohex is relevant to pharmaceutical manufacturing and process chemistry as a protected lysine building block that can be incorporated into peptide or peptide-like intermediate streams. The orthogonal protection pattern helps manage chemoselectivity during scale-up by allowing controlled deprotection and coupling sequences that reduce side reactions from unprotected amines. The stable Boc and Alloc carbamate/ carbonate functionalities support predictable intermediate handling, while the D-lysine stereocenter maintains defined stereochemical identity for downstream synthetic specifications. The dicyclohex counterion form can be utilized to support manufacturable solid-state properties and downstream conversion to free amine-containing intermediates for fine chemical synthesis and specialty chemical production.
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