Nps-Met-OH · DCHA is a methionine-based amino acid derivative in which the side chain corresponds to the thioether-bearing methionine structure and the α-carboxylic acid and α-amino group are present as part of the free amino acid framework. The molecule is associated with DCHA (dicyclohexylamine), forming an amino acid salt that modulates the counterion environment around the basic amino functionality, while "Nps" indicates an N-substituted amino component that alters the nitrogen's reactivity relative to an unprotected methionine. In synthesis and analytical workflows, this salt-form protected/derivatized methionine analogue can be used as a controlled precursor for preparing further amino acid and peptide derivatives, including incorporation steps where the modified nitrogen functionality and salt form influence handling, solubility, and chemoselectivity.
Nps-Met-OH · DCHA is a salt-form protected amino acid derivative consisting of an Nps-protected methionine acid (Met-OH) associated with dicyclohexylamine (DCHA). The molecule retains the methionine stereochemical configuration at the α-carbon while presenting a carboxylic acid handle for peptide coupling and an Nps (p-nitrophenylsulfenyl) protecting group on the amino functionality. The thioether side chain of methionine remains present as a sulfur-containing nucleophile that can participate in redox-sensitive transformations or side-chain derivatization, while the Nps group provides controlled amine unmasking compatible with peptide synthesis workflows. The salt pairing with DCHA can influence crystallinity, handling, and downstream conversion steps, making the compound suitable as a chiral amino acid intermediate for protected amino acid chemistry and peptide building block preparation.
1. Peptide Synthesis
Nps-Met-OH · DCHA is applied in peptide coupling chemistry where the protected methionine amino group and free carboxylic acid enable stepwise amide bond formation under standard peptide synthesis conditions. The Nps protection strategy supports orthogonal deprotection logic, allowing selective removal of the sulfenyl-type N-protecting group to generate the reactive amine for subsequent coupling while maintaining the integrity of the methionine side-chain thioether. The retained α-stereocenter supports stereochemically defined peptide assembly, which is relevant for producing sequence-specific Met-containing peptides and peptide fragments. The DCHA salt form can be leveraged to improve process handling and consistency during protected amino acid addition, supporting reliable peptide building block preparation for research and manufacturing-scale synthesis.
2. Side-Chain Functionalization
Nps-Met-OH · DCHA supports side-chain functionalization programs that exploit the methionine thioether as a sulfur-containing functional handle for downstream derivatization. The compound's structure preserves the thioether while keeping the amino functionality protected, enabling selective transformations focused on the side-chain without prematurely engaging the amine. The carboxylic acid can be converted into activated derivatives or used as a handle for conjugation strategies after controlled deprotection, supporting generation of Met analogs used in chemical biology and peptidomimetic construction. The resulting sulfur-functionalized methionine derivatives can serve as intermediates for redox-responsive probes, affinity tags, or scaffold modifications that maintain stereochemical fidelity from the protected amino acid precursor.
3. Protected Amino Acid Chemistry
Nps-Met-OH · DCHA is used as a chiral, N-protected amino acid intermediate for protected amino acid synthesis, where the Nps group provides a sulfenyl-based amine protection platform compatible with peptide-grade building block workflows. The free carboxylic acid enables conversion to coupling-ready forms while the Nps protection helps manage reactivity during multi-step synthesis, including protection/deprotection sequencing and purification-friendly handling. The methionine thioether can be carried through orthogonal steps, supporting synthetic routes that require preservation of sulfur functionality until a defined downstream stage. The DCHA salt association can be applied to manufacturing-relevant crystallization and isolation logic, supporting reproducible preparation of protected amino acid inputs for fine chemical synthesis and industrial peptide intermediate production.
4. Chemical Biology Probes
Nps-Met-OH · DCHA is suitable for chemical biology research requiring Met-containing peptide building blocks or amino acid derivatives that incorporate a sulfur side chain for probe design. The combination of an α-carboxyl group and an Nps-protected amine supports controlled assembly of labeled peptides, where subsequent deprotection and coupling can introduce reporter moieties or capture handles. The methionine thioether can participate in chemically addressable transformations, enabling construction of probes that respond to redox conditions or that allow selective conjugation after defined activation steps. The chiral amino acid backbone ensures stereochemically consistent incorporation into peptide scaffolds used for molecular recognition studies, biomolecule modification, and mechanistic investigations of peptide-protein interactions.
5. Pharmaceutical Manufacturing Intermediates
Nps-Met-OH · DCHA can be employed in pharmaceutical manufacturing supply chains as a protected methionine acid intermediate for producing Met-containing peptide intermediates and peptidomimetic precursors. The free carboxylic acid and Nps-protected amine support controlled coupling chemistry in upstream synthesis of defined sequences, while the preserved thioether side chain supports later functionalization steps required for scaffold diversification. The salt form with DCHA aligns with industrial handling considerations such as isolation, storage stability, and consistent feedstock behavior during protected amino acid addition. The compound thereby serves as a process-compatible building block for specialty chemical production and chemical manufacturing routes that require stereodefined amino acid inputs and predictable protection-group behavior for downstream intermediate formation.
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