Nps-Lys(Boc)-OH · DCHA is a protected lysine amino acid derivative featuring an Nps (p-nitrophenylsulfenyl) group on the α-amino functionality and a tert-butoxycarbonyl (Boc) protecting group on the ε-amino side chain, with a free carboxylic acid at the C-terminus. The molecule contains the lysine backbone bearing a basic side-chain nitrogen that is masked by Boc, while the Nps sulfenyl protection is designed to control chemoselectivity at the protected nitrogen during stepwise assembly of peptide fragments. As an amino acid building block, it is used in peptide synthesis workflows to manage orthogonality between amino functionalities and to support the preparation of lysine-containing peptide intermediates and labeled or modified peptide constructs.
CAT No: CP26960
CAS No:2896-69-7
Synonyms/Alias:Nps-Lys(Boc)-OH.DCHA;2896-69-7
Nps-Lys(Boc)-OH · DCHA is a lysine-based amino acid derivative presented as a salt with dicyclohexylamine (DCHA), featuring a protected ε-amino group as a Boc carbamate and a side-chain nucleophile masked to support controlled peptide chemistry. The Nps (p-nitrophenylsulfenyl) protection on the α-amino functionality provides an electrophile-compatible, removable amino protecting strategy that can be orthogonally deprotected under conditions used for sulfenyl groups. The molecule contains a free carboxylic acid (-CO2H) for coupling, while the Boc group and the sulfenyl-derived Nps moiety modulate basicity and reactivity during synthesis and purification. The chiral lysine backbone and the salt form influence solubility and handling, making the compound suitable as a chiral amino acid intermediate for protected amino acid synthesis and downstream peptide building block preparation.
1. Peptide Synthesis
Nps-Lys(Boc)-OH · DCHA supports peptide coupling workflows in peptide synthesis and solid-phase or solution-phase assembly by providing a carboxylic acid for amide bond formation and a protected lysine side chain to control chemoselectivity. The Boc-protected ε-amine reduces side reactions such as undesired branching or crosslinking during activation and coupling, while the Nps α-amino protection can be managed to enable stepwise construction of peptide sequences with defined N-terminal identity. The DCHA salt form can improve practical handling and reproducible reactivity by modulating salt-related solubility and buffering behavior in coupling media. The resulting protected lysine building block can be incorporated into peptide fragments and longer constructs, enabling controlled generation of lysine-containing peptides and peptide analogs used in biochemical research and structure-function studies.
2. Chemical Biology
Nps-Lys(Boc)-OH · DCHA is applicable in chemical biology where lysine-specific functional group placement is required for probe design, affinity reagents, and molecular recognition studies. The protected lysine side chain allows installation of functional handles after deprotection, leveraging the ε-amino chemistry for subsequent derivatization such as acylation, sulfonylation, or conjugation to electrophilic tags. The Nps and Boc protecting-group set supports sequential manipulation of the α-amino and ε-amino functionalities, enabling controlled generation of mono-functionalized or site-defined lysine derivatives for labeling strategies. Downstream products can serve as intermediates for bioconjugation reagents, enabling reproducible attachment patterns in biochemical assays and molecular tool development.
3. Peptidomimetics
Nps-Lys(Boc)-OH · DCHA can be used in peptidomimetic construction and medicinal chemistry intermediate preparation where lysine-derived stereodefined scaffolds are required. The free carboxylic acid and protected amine groups enable conversion into activated intermediates for incorporation into non-natural peptide backbones, including analogs that retain lysine side-chain spacing while altering backbone stability. The Boc carbamate and Nps sulfenyl protection provide a route to manage chemoselective transformations, supporting selective deprotection and subsequent functionalization of the ε-amino group for incorporation into amide-linked or substituted heterocycle-containing motifs. The chiral lysine framework can thus feed into downstream synthetic sequences that generate peptidomimetic libraries and structure-activity relationship (SAR) focused analogs.
4. Protected Amino Acids
Nps-Lys(Boc)-OH · DCHA serves as a protected amino acid chemistry intermediate for manufacturing and research-grade peptide building block preparation, combining a carboxylic acid handle with orthogonally managed amine protection. The Boc group on the ε-amine provides a stable protecting strategy during activation chemistry, while the Nps α-amino protection supports controlled deprotection logic aligned with peptide synthesis requirements. The DCHA salt form can be leveraged in process chemistry to improve handling characteristics and reproducibility of solid-state properties during weighing, dissolution, and coupling preparation. The compound can be employed to prepare lysine-containing protected fragments for fine chemical synthesis, supporting consistent downstream coupling performance and enabling scalable access to protected lysine derivatives.
5. Bioconjugation Chemistry
Nps-Lys(Boc)-OH · DCHA is suitable for bioconjugation chemistry workflows that require site-defined lysine incorporation into conjugates and labeling reagents. The lysine side-chain ε-amino group, masked as a Boc carbamate, can be selectively revealed after appropriate protecting-group removal to enable controlled attachment to activated esters, isothiocyanates, aldehyde-based linkers, or other electrophilic conjugation partners. The Nps-protected α-amino functionality supports controlled preparation of amino acid derivatives with defined N-terminal reactivity, which can be important for generating conjugates with predictable orientation and reduced heterogeneity. The downstream lysine-functional conjugation products can be used as intermediates for analytical standards, affinity reagents, and molecular probes in applied biochemical research and industrial fine chemical production.
6. Process Chemistry Intermediate
Nps-Lys(Boc)-OH · DCHA can be applied in process chemistry intermediate preparation where protected amino acid salts and orthogonally protected lysine building blocks support scalable manufacturing routes. The presence of a free carboxylic acid enables conversion into coupling-ready activated derivatives under standard peptide-manufacturing conditions, while the Boc and Nps protections help regulate amine reactivity and minimize side reactions during multi-step sequences. The DCHA salt form is relevant to industrial handling, as it can influence dissolution rate, crystallization behavior, and storage stability of the protected amino acid material. The compound therefore functions as a chiral amino acid intermediate that can be incorporated into larger manufacturing flows for peptide building blocks, specialty chemical production, and downstream generation of lysine-containing intermediates used across biochemical and industrial synthesis programs.
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