D-Valine tert.butyl ester hydrochloride is a D-configured amino acid ester derived from valine, featuring the isopropyl side chain characteristic of branched-chain amino acids and an esterified carboxyl group. The molecule contains a free amino functionality in the form of a hydrochloride salt, while the carboxyl group is protected as a tert-butyl ester that can be removed under acidic conditions to regenerate the corresponding amino acid for subsequent coupling chemistry. In peptide and amino acid derivative synthesis, it functions as a protected, esterified D-valine building block that supports stepwise assembly by temporarily masking the carboxyl group and providing a defined, salt-stabilized form for handling and reagent preparation.
CAT No: CP02230
CAS No:104944-18-5
Synonyms/Alias:104944-18-5;H-D-Val-OtBuHCl;D-Valinetert-butylesterhydrochloride;H-D-Val-OtBu.HCl;(R)-tert-butyl2-amino-3-methylbutanoatehydrochloride;tert-butyl(2R)-2-amino-3-methylbutanoatehydrochloride;D-Valinetert.butylesterhydrochloride;H-D-Val-OtBuCl;H-D-Val-OtBu?HCl;KSC698A5L;SCHEMBL919725;CTK5J8055;AUIVQIHTTVPKFS-OGFXRTJISA-N;MolPort-020-004-718;tert-butylD-valinatehydrochloride;ACN-S002369;CH-335;FD3070;D-VALINETERT.BUTYLESTERHCL;AKOS015894512;AM82374;NE11427;RL00233;AK-49226;AM011607
D-Valine tert.butyl ester hydrochloride is the hydrochloride salt of the tert-butyl ester of D-valine, a chiral amino acid derivative featuring a D-configured α-carbon and a branched isopropyl side chain. The molecule presents a protected carboxyl functionality as a tert-butyl ester, while the amino group is present as an ammonium chloride salt, which modulates nucleophilicity and improves handling of the chiral intermediate. The ester group provides a removable protecting strategy compatible with acid-mediated deprotection, enabling controlled conversion back to the free carboxylic acid for subsequent peptide coupling. The stereodefined D-valine backbone and side-chain hydrophobicity support incorporation into dipeptides, peptide fragments, and stereochemically defined amino acid sequences used in synthetic and biochemical research.
1. Protected Amino Acid Chemistry
D-Valine tert.butyl ester hydrochloride is used in protected amino acid synthesis workflows where a stable, ester-masked carboxyl group is required for downstream amide bond formation. The tert-butyl ester functionality can be carried through coupling steps while limiting premature reactions of the carboxyl group, and the D-stereochemistry preserves stereochemical integrity of the valine residue. Hydrochloride salt formation helps maintain the amino group in a controlled protonation state during intermediate handling and can support compatibility with standard peptide coupling chemistries after appropriate activation. The resulting D-valine building block format enables stepwise construction of peptide chains and preparation of stereochemically defined intermediates for fine chemical synthesis.
2. Peptide Synthesis Building Blocks
D-Valine tert.butyl ester hydrochloride serves as a peptide building block precursor for assembling D-valine-containing peptides and peptide fragments in peptide chemistry and peptidomimetic construction. The amino acid backbone provides the functional elements needed for peptide coupling once the ester protection strategy is managed, while the branched isopropyl side chain contributes hydrophobic character that can influence conformational preferences in short sequences. The tert-butyl ester protection strategy supports orthogonal manipulation relative to other side-chain protecting groups, and the D-configuration enables stereochemical control for unnatural peptide architectures. Downstream peptide analogs prepared from this chiral intermediate can be used to probe sequence-dependent properties and to generate defined substrates for biochemical assays.
3. Chiral Intermediate For SAR Studies
D-Valine tert.butyl ester hydrochloride is applied in SAR studies and molecular design programs that require enantiopure amino acid components for constructing stereochemically defined analog libraries. The D-amino acid stereocenter provides a direct handle for generating diastereomer- or enantiomer-specific peptide variants, supporting structure-activity relationship investigations driven by stereochemistry. The tert-butyl ester group functions as a protected carboxyl handle that can be converted to the corresponding acid form when building larger scaffolds or preparing activated derivatives for coupling. The compound's chiral amino acid identity supports downstream fragment assembly and systematic variation of peptide-like motifs used in medicinal chemistry research.
4. Bioconjugation And Linker Chemistry
D-Valine tert.butyl ester hydrochloride can be incorporated into bioconjugation and chemical biology workflows where amino acid-derived linkers or peptide handles are required for controlled attachment to biomolecular targets. The protected carboxyl group and amino functionality enable stepwise derivatization into amide-forming intermediates that can be coupled to activated biomolecule-reactive groups under standard conjugation chemistries. The D-valine residue can be used to adjust proteolytic stability and influence local hydrophobic interactions in conjugate constructs, which is relevant for designing peptide-based labeling reagents and stable biomolecule modifiers. The hydrochloride salt form supports practical handling of the chiral intermediate prior to conversion into coupling-ready derivatives.
5. Pharmaceutical Intermediate Preparation
D-Valine tert.butyl ester hydrochloride is suitable for pharmaceutical intermediate preparation and process chemistry routes that require a protected, stereodefined amino acid precursor. The tert-butyl ester provides a manufacturing-compatible protection strategy for temporarily masking the carboxyl group during synthetic sequence design, while the D-configuration supports consistent stereochemical outcomes across batch production. Hydrochloride salt formation can improve solid-state handling and can be leveraged in process steps that require controlled protonation states before activation and coupling. The material can serve as a chiral feedstock for producing D-valine-containing intermediates used in the synthesis of peptide-like active ingredients, peptidomimetic scaffolds, and related specialty fine chemicals.
6. Analytical And Reference Standard Development
D-Valine tert.butyl ester hydrochloride is used in analytical research for preparing stereochemically defined reference materials and method development samples in amino acid and peptide analysis. The combination of a protected ester and a defined D-configuration supports unambiguous chromatographic and mass spectrometric characterization of derivatized amino acid species and peptide fragments derived therefrom. The hydrochloride salt form can aid reproducible sample preparation when evaluating ionization behavior and salt-state effects in LC-MS workflows. The compound's role as a defined chiral intermediate supports calibration, impurity profiling, and verification of stereochemical integrity during peptide building block synthesis and downstream scaffold assembly.
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