H-DL-Leu-OMe · HCl is a hydrochloride salt of the methyl ester of a leucine amino acid derivative, featuring an aliphatic isobutyl side chain characteristic of the leucine class and a free amino group in the esterified form. The molecule bears a carboxyl group protected as a methyl ester (-CO2Me) and is present as the amino hydrochloride (HCl), which provides ionic stabilization while retaining the side-chain hydrophobic functionality associated with leucine. As an amino acid ester salt, it is used as a protected/derivatized leucine building block for peptide and amide bond formation in solution-phase or stepwise synthesis, and it can also serve as a substrate or reference material in analytical method development where esterified amino acid forms are required.
CAT No: CP27299
CAS No:6322-53-8
Synonyms/Alias:D-threonine;632-20-2;(2R,3S)-2-amino-3-hydroxybutanoicacid;H-D-Thr-OH;Threonine,D-;D-Threonin;(R)-Threonine;D-2-Amino-3-hydroxybutyricacid;(2R,3S)-2-Amino-3-hydroxybutyricacid;AYFVYJQAPQTCCC-STHAYSLISA-N;EINECS211-171-8;NSC46702;D-alpha-Amino-beta-hydroxybutyricacid;BRN1721643;DTH;(+/-)-2-Amino-3-hydroxybutyricacid;6028-28-0;D-(+)-Threonine;AmbotzHAA1053;PubChem13029;PubChem20724;AC1L2BV5;AC1Q29LW;SCHEMBL92731;KSC352S5H
H-DL-Leu-OMe · HCl is a hydrochloride salt of the methyl ester of leucine, presenting a chiral amino acid framework with a leucine side chain (isobutyl) and an amino group present as a protonated salt. The molecule combines an amino acid ester functionality with salt-mediated handling characteristics that can improve stability during storage and facilitate controlled reactivity in coupling and derivatization sequences. The N-terminal amino functionality is protected only by its ester/salt form rather than a classical acyl protecting group, while the carboxylate equivalent is masked as a methyl ester that can be selectively transformed into amides, acids, or activated derivatives. The DL stereochemical composition provides access to racemic leucine-based building blocks for method development, intermediate screening, and downstream chiral resolution workflows in amino acid chemistry and peptide synthesis.
1. Peptide Coupling Building Block
H-DL-Leu-OMe · HCl is applied in peptide synthesis workflows as a leucine methyl ester hydrochloride that can participate in amide bond formation after conversion to an appropriate reactive amino component. The amino group, present as a hydrochloride salt, supports controlled activation and can be paired with carboxylic acid derivatives or activated ester species to build leucine-containing peptide fragments. The methyl ester handle enables downstream transformations such as ester hydrolysis to the corresponding acid for iterative chain extension or conversion to coupling-ready forms. Racemic stereochemistry can be leveraged for library construction, coupling condition optimization, or as a feedstock for later stereochemical enrichment during peptide building block preparation.
2. Amino Acid Ester Derivatization
H-DL-Leu-OMe · HCl is well suited for amino acid derivatization and process chemistry intermediate preparation where the methyl ester provides a practical functional group for selective reactivity management. The ester group can be hydrolyzed to the carboxylic acid for subsequent activation, or transesterified and re-functionalized to generate alternative protecting-group patterns compatible with peptide coupling strategies. The leucine side-chain hydrophobicity supports formation of lipophilic intermediates used in synthetic organic chemistry for scaffold modification and intermediate tuning. The DL composition enables parallel synthesis of stereochemical variants, supporting method development for ester-to-amide conversion and downstream functional group transformation in industrial fine chemical synthesis.
3. Chiral Resolution Feedstock
H-DL-Leu-OMe · HCl is used as a racemic chiral amino acid intermediate for resolution strategies that separate enantiomers of leucine derivatives prior to stereodefined peptide construction. The presence of a free amino functionality as a salt and a methyl ester allows formation of diastereomeric derivatives with chiral acids or chiral derivatizing agents, enabling analytical or preparative separation routes. The isobutyl side chain maintains the stereochemical information at the alpha-carbon while providing robust mass balance for downstream conversion to enantiopure amino acid building blocks. The resulting enantiomer-enriched leucine ester or its hydrolyzed acid can then be incorporated into protected amino acid synthesis and stereochemically defined peptide analog preparation.
4. Pharmaceutical Intermediate Synthesis
H-DL-Leu-OMe · HCl can be employed in pharmaceutical intermediate synthesis as a leucine-based amino acid ester that feeds into amide-forming sequences and side-chain functionalization routes. The amino ester motif supports conversion into carboxyl-activated intermediates and amide derivatives used in medicinal chemistry for generating peptidomimetic fragments and constrained analogs. The hydrochloride salt form can simplify handling in multistep manufacturing where consistent reagent behavior is required for reproducible coupling chemistry. Downstream hydrolysis or functional group interconversion can yield leucine-derived acids or activated species suitable for further synthetic elaboration toward bioactive-molecule scaffolds and process-ready intermediates.
5. Analytical Research Standard Development
H-DL-Leu-OMe · HCl is suitable for analytical research and method development where leucine ester standards and racemic reference materials support chromatographic and spectrometric characterization. The methyl ester and amino salt combination provides a defined chemical form that can be monitored by LC-MS, GC-MS after derivatization, or NMR-based quantification in amino acid ester analyses. The DL stereochemistry supports calibration of racemate behavior and can be used to validate stereochemical separation methods when paired with chiral stationary phases or derivatization workflows. Leucine-derived ester standards also enable verification of intermediate identity in protected amino acid synthesis sequences and peptide coupling chemistry development.
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