N-α-Benzyl-D-Valine methyl ester hydrochloride is a protected amino acid derivative featuring the D-valine backbone with a methyl ester at the carboxyl terminus and an N-α benzyl substituent on the amino nitrogen. The molecule contains an amino acid side chain characteristic of valine (isopropyl group) and is present as a hydrochloride salt, which is consistent with protonation of the amino functionality and can influence solubility and handling during synthesis. In peptide and amino acid chemistry workflows, the benzyl-protected nitrogen and methyl ester functionality provide chemoselective control for stepwise derivatization or incorporation into larger peptide-related intermediates, while the D stereochemical form supports stereochemically defined structure-activity and analytical studies.
CAT No: CP02211
N-α-Benzyl-D-Valine methyl ester hydrochloride is a D-valine-derived amino acid ester in which the α-amino group is N-benzylated and present as a hydrochloride salt, while the carboxyl functionality is converted to a methyl ester. The molecule retains the branched isopropyl side chain characteristic of valine, providing a hydrophobic stereogenic environment around the D-configured α-carbon. The N-benzyl group and ester carbonyl establish distinct reactivity handles for peptide coupling compatibility and subsequent functional group interconversion. Salt formation with HCl improves handling of the basic nitrogen during synthesis, while the ester and protected amine enable downstream conversion into peptide building blocks or chiral intermediates for fine chemical production.
1. Peptide Synthesis
N-α-Benzyl-D-Valine methyl ester hydrochloride is used in peptide building block preparation where the methyl ester can be transformed into an activated C-terminal functionality for coupling chemistry. The N-benzyl-protected amino group supports orthogonal protection strategies, allowing selective deprotection or activation steps that preserve the D-stereochemistry at the α-carbon. Hydrochloride salt formation can facilitate controlled handling during solid-phase or solution-phase workflows that require stable amino ester intermediates. The resulting protected amino acid derivative can be incorporated into short peptides and peptide fragments, supporting structure-activity relationship studies and peptidomimetic construction from D-amino acid scaffolds.
2. Chiral Building Blocks
N-α-Benzyl-D-Valine methyl ester hydrochloride serves as a chiral amino acid intermediate for stereoselective synthesis, leveraging the D-configuration and the valine side-chain geometry. The N-benzyl protection provides a robust nitrogen handle that can be maintained during ester-based transformations and later removed when amine unveiling is required for further derivatization. The methyl ester enables controlled conversion to carboxylic acids, acid chlorides, or other acylating agents, supporting the preparation of enantiopure fragments used in asymmetric synthesis campaigns. Downstream use commonly includes generating D-valine-based chiral ligands, stereodefined amide linkers, and intermediate streams for specialty chemical production.
3. Amino Acid Derivatization
N-α-Benzyl-D-Valine methyl ester hydrochloride is applicable to amino acid derivatization workflows that require both nitrogen protection and an ester functional group for staged chemistry. The ester carbonyl participates in hydrolysis, transesterification, and selective activation routes that can convert the intermediate into C-terminal carboxylic acid derivatives or activated acyl species for subsequent bond formation. The N-benzylated amine can be used to regulate chemoselectivity during side-chain functionalization sequences that target the valine-derived hydrophobic region without disturbing the α-amino stereocenter. Salt-associated handling further supports reproducible intermediate preparation for generating libraries of N-protected D-amino acid derivatives used in synthetic organic chemistry and chemical biology reagent development.
4. Bioconjugation Chemistry
N-α-Benzyl-D-Valine methyl ester hydrochloride can be used as a precursor for bioconjugation reagents where a D-amino acid motif is incorporated into linker architectures. The protected amine and ester functionality enable conversion into amide-forming intermediates and controlled attachment points for coupling to carboxyl- or amine-bearing biomolecules. The D-stereochemistry can be retained through the intermediate stage to support incorporation of stereodefined linkers that may influence conformational preferences and protease resistance in conjugate designs. Downstream derivatives prepared from this intermediate can support labeling strategies, affinity tag construction, and biomolecule modification efforts requiring chemically defined amino acid-based linkers.
5. Pharmaceutical Intermediate Preparation
N-α-Benzyl-D-Valine methyl ester hydrochloride is suitable for pharmaceutical intermediate preparation in synthetic routes that require D-amino acid incorporation and orthogonal functional group management. The methyl ester and N-benzyl protection provide a protected amino acid ester form that can be advanced into acylating agents or amide intermediates used for medicinal chemistry building blocks. Hydrochloride salt formation supports handling of the amino functionality during multi-step synthesis where controlled deprotection timing is required to avoid side reactions. The valine side-chain offers a hydrophobic fragment that can be embedded into peptidomimetic or constrained scaffold intermediates, supporting process chemistry intermediate generation and fine chemical synthesis workflows.
3. C-Peptide replacement therapy and sensory nerve function in type 1 diabetic neuropathy
5. Immune-awakening Saccharomyces-inspired nanocarrier for oral target delivery to lymph and tumors
If you have any peptide synthesis requirement in mind, please do not hesitate to contact us at . We will endeavor to provide highly satisfying products and services.
Creative Peptides is a trusted CDMO partner specializing in high-quality peptide synthesis, conjugation, and manufacturing under strict cGMP compliance. With advanced technology platforms and a team of experienced scientists, we deliver tailored peptide solutions to support drug discovery, clinical development, and cosmetic innovation worldwide.
From custom peptide synthesis to complex peptide-drug conjugates, we provide flexible, end-to-end services designed to accelerate timelines and ensure regulatory excellence. Our commitment to quality, reliability, and innovation has made us a preferred partner across the pharmaceutical, biotechnology, and personal care industries.
Read More