H-L-Chg-OH*HCl is a free amino acid derivative presented as the hydrochloride salt, where the side chain contains a cyclic guanidinium-like functionality (Chg) attached to an alpha-amino acid backbone bearing a carboxylic acid. The molecule contains an amino group and a carboxyl group, and the "*HCl" indicates protonation/ion pairing that increases water solubility and helps maintain the cationic character of the basic side chain for handling and coupling chemistry. As a salt form of a basic, side-chain-functional amino acid, it is used as a building block for peptide synthesis and for preparing amino acid and peptide derivatives that require a guanidinium-type group for charge-mediated interactions, conjugation, or structure-activity studies.
CAT No: CP25352
CAS No:14328-51-9
Chemical Name:L-Cyclohexylglycine hydrochloride
L-Homochg-OH*HCl is the hydrochloride salt of an L-configured amino acid derivative featuring a chiral center and a free carboxylic acid functionality, with a side chain that can participate in stereochemically defined transformations. The salt form introduces a protonated amine environment that improves handling and can influence coupling behavior in peptide chemistry by moderating nucleophilicity until appropriate base conditions are applied. The presence of a carboxyl group and a stereodefined carbon skeleton makes the compound suitable for conversion into protected amino acid derivatives, amino acid esters, and activated coupling intermediates. The overall reactivity profile supports downstream synthetic utility as a chiral building block for amino acid derivatization and peptide or peptidomimetic scaffold construction.
1. Peptide Synthesis
L-Homochg-OH*HCl is applied in peptide synthesis workflows where an L-configured amino acid building block is required for stereochemically controlled chain extension. The carboxylic acid and amino functionality enable conversion into N-protected amino acid derivatives and C-terminal activated species for peptide coupling chemistry, including strategies that manage salt-associated protonation states. Side-chain features can be preserved or selectively functionalized depending on the chosen protection pattern, supporting orthogonal deprotection sequences during stepwise assembly. The hydrochloride form can serve as a convenient starting point for preparing protected intermediates used in solid-phase or solution-phase peptide construction, including analog libraries.
2. Amino Acid Derivatization
L-Homochg-OH*HCl is used as a chiral amino acid intermediate for amino acid derivatization and functional group interconversion in synthetic organic chemistry. The free carboxyl group can be esterified, amidated, or converted to activated carboxyl derivatives, while the amino functionality can be protected to control chemoselectivity during side-chain modification. Stereochemical integrity of the L-configured center supports the synthesis of enantiopure derivatives used in structure-activity relationship studies and molecular design campaigns. Downstream products can include functionalized amino acid esters, amides, and protected intermediates that feed into peptide building block preparation and further synthetic elaboration.
3. Chiral Building Block Development
L-Homochg-OH*HCl is suitable as a chiral amino acid intermediate for developing enantiopure building blocks used in fine chemical synthesis and chiral pool-inspired route design. The defined stereocenter and the acid/amine functional set allow transformation into protected amino acid derivatives that maintain stereochemical fidelity through protection, activation, and coupling steps. The hydrochloride salt can be leveraged for reproducible handling while still allowing conversion to free-base or protected forms prior to coupling or derivatization operations. Resulting chiral intermediates can be employed to construct peptidomimetics, incorporate stereodefined fragments into larger scaffolds, and support stereochemical studies requiring consistent configuration.
4. Bioconjugation Chemistry
L-Homochg-OH*HCl can be applied in chemical biology and bioconjugation chemistry as a precursor to amino acid-based handles for controlled attachment to biomolecules. The carboxyl functionality can be transformed into activated esters or amide-forming intermediates, while the amino group can be protected or selectively deprotected to enable conjugation under compatible conditions. Side-chain reactivity can be tuned through protection-group selection to minimize undesired cross-reactivity with biomolecule nucleophiles and to support defined coupling sites. Prepared derivatives from this hydrochloride salt can be used to generate amino acid-containing conjugates for analytical research, biomolecule modification, and scaffold labeling strategies.
5. Pharmaceutical Manufacturing Intermediates
L-Homochg-OH*HCl is relevant to pharmaceutical manufacturing and process chemistry as a chiral intermediate that can be routed into protected amino acid derivatives for downstream synthesis of peptide-like or amino acid-containing intermediates. The acid and amino functionalities allow integration into established manufacturing sequences where N-protection and carboxyl activation are used to control reaction order and impurity profiles. The hydrochloride salt form supports practical material handling and can be converted into the appropriate protected or activated forms required for coupling steps in bulk synthesis. Process-compatible derivatives derived from this starting material can serve as inputs for specialty chemical production, including the preparation of stereodefined fragments used in industrial-scale fine chemical synthesis.
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