H-D-Val-OMe*HCl is a deuterated valine methyl ester hydrochloride, belonging to the amino acid ester class and featuring a valine-derived α-amino acid framework with a methyl ester (-COOCH3) at the carboxyl terminus. The molecule bears an amino group in protonated form as indicated by the hydrochloride salt, and the "H-D" designation specifies incorporation of deuterium at one or more hydrogen positions on the valine skeleton while the side chain retains the isopropyl functionality characteristic of valine. As an isotopically labeled amino acid ester, it is used in chemical labeling and analytical method development, including studies that require deuterium incorporation for mass spectrometric detection, isotopic tracing, or quantification of ester-containing valine derivatives in peptide-related synthesis workflows.
CAT No: CP26005
CAS No:7146-15-8
Chemical Name:D-Valine methyl ester hydrochloride
H-D-Val-OMe*HCl is a protected valine methyl ester hydrochloride in which the amino group is acetylated (N-acetyl, H-D- prefix) and the carboxyl functionality is present as a methyl ester salt (OMe*HCl). The molecule retains the branched isopropyl side chain characteristic of valine, while the ester and N-acetyl groups modulate polarity and control chemoselectivity during peptide coupling and subsequent transformations. The D-configuration at the amino acid stereocenter provides a defined chiral building block for stereochemically controlled peptide analogs and unnatural amino acid incorporation. The hydrochloride counterion stabilizes the esterified amino acid as a crystalline or isolable salt form, enabling practical handling in synthetic sequences that require protected amino acid chemistry.
1. Peptide Synthesis
H-D-Val-OMe*HCl is used in peptide synthesis as a D-valine methyl ester building block where the N-acetyl group and ester functionality support controlled coupling and downstream deprotection logic. The presence of a defined chiral center enables incorporation of D-valine into peptide chains to modulate backbone stereochemistry and protease resistance profiles in peptide analogs. The ester form can participate in standard amino acid ester chemistry for C-terminal derivatization strategies, while the N-acetyl protection can be removed or transformed under conditions compatible with peptide assembly workflows. Peptide coupling compatibility makes this compound suitable for constructing short peptide segments, including D-amino acid-containing fragments used in biochemical research and peptidomimetic design.
2. Unnatural Amino Acid Incorporation
H-D-Val-OMe*HCl serves as a chiral intermediate for unnatural amino acid incorporation in chemical biology and medicinal chemistry research programs. The D-valine stereochemistry, combined with N-acetyl protection and methyl ester masking, allows selective introduction of a stereodefined residue into peptide scaffolds without exposing the amino acid to uncontrolled side reactions. The branched side chain provides a hydrophobic handle that can be positioned within peptide sequences to probe sequence-dependent conformational effects and structure-activity relationship trends. The resulting D-valine-containing derivatives can be extended into larger peptide constructs or converted into functional analogs for SAR studies and molecular design campaigns.
3. Peptidomimetic Construction
H-D-Val-OMe*HCl is applied in peptidomimetic construction where amino acid ester and N-acyl features support iterative assembly of constrained or modified peptide-like structures. The methyl ester can be used as a C-terminal functional group precursor for conversion into amides, linkers, or other carboxyl-derived motifs during scaffold elaboration. The N-acetyl-protected amine can be retained or adjusted to match coupling chemistries used for assembling peptidomimetics, including sequences that incorporate stereochemically inverted residues. Downstream formation of D-valine-containing analogs enables systematic exploration of backbone stereochemistry effects on binding conformations and chemical stability in research workflows.
4. Analytical Standards And Labeling
H-D-Val-OMe*HCl can be employed in analytical research as a stereochemically defined reference material for method development involving D-amino acid-containing peptides and derivatives. The stable salt form and protected functional groups facilitate handling when preparing calibration standards, derivatization reagents, or internal standards that require consistent stereochemical identity. The methyl ester and N-acetyl protection pattern supports predictable chromatographic behavior and can be leveraged to verify conversion states during synthetic monitoring. The compound's defined structure also supports downstream synthesis of labeled or derivatized valine-containing fragments used in LC-MS, chiral HPLC, or targeted compositional analysis.
5. Pharmaceutical Intermediate Preparation
H-D-Val-OMe*HCl is suitable for pharmaceutical intermediate preparation in fine chemical synthesis where D-amino acid residues are incorporated into peptide-based or peptide-derived intermediates. The protected amino acid architecture, featuring N-acetylation and esterification, aligns with industrially relevant protection/deprotection strategies that enable controlled coupling steps and minimized side reactions. The stereodefined D-center supports manufacturing routes that require consistent stereochemical outcomes across scale-up batches. The compound can be converted into larger protected amino acid derivatives or C-terminal intermediates, supporting the generation of D-valine-containing building blocks for downstream synthesis of peptide analogs and related functional molecules.
6. Process Chemistry For Protected Amino Acids
H-D-Val-OMe*HCl is relevant to process chemistry for protected amino acid manufacturing where isolable salt forms and protected functional groups improve operational control. The hydrochloride counterion helps stabilize the amino ester as a discrete feed material, which can simplify handling in multi-step sequences that include coupling, ester-to-amide conversion, or terminal functional group adjustments. N-acetyl and methyl ester functionalities provide chemoselective behavior that can be matched to common industrial protection-group strategies, including selective deprotection while preserving side-chain integrity. The compound's role as a chiral amino acid intermediate supports reproducible synthesis of D-valine-containing peptide building blocks used in applied product development and specialty chemical production.
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