Bzl-L-Ile-OMe*HCl

Bzl-L-Ile-OMe*HCl is an L-isoleucine methyl ester hydrochloride bearing a benzyl (Bzl) protecting group on the amino functionality, giving a chiral amino acid ester salt with a stereogenic center at the Ile α-carbon and a branched hydrophobic side chain. The structure combines an N-benzyl-protected amine with a methyl ester that can participate in peptide coupling chemistry after appropriate activation, while the hydrochloride form improves handling and can influence salt-mediated reactivity and solubility during synthetic steps. The benzyl group provides a stable N-protection strategy compatible with many peptide synthesis conditions and can be removed under hydrogenolysis to regenerate the free amine for subsequent coupling. The overall reactivity profile makes the compound suitable as a chiral amino acid ester intermediate and protected amino acid building block for downstream derivatization, peptide assembly, and stereochemically defined fragment construction.

1. Protected Amino Acid Chemistry

Bzl-L-Ile-OMe*HCl serves as a protected amino acid ester for N-protection and controlled peptide coupling workflows in synthetic organic chemistry. The benzyl-protected amine and methyl ester functional groups enable orthogonal handling: the N-protection can remain intact through activation steps, while the ester can be converted to an activated carboxyl derivative or transformed into other C-terminal formats as needed. The hydrochloride salt form can facilitate reproducible salt formation and handling during intermediate preparation, supporting consistent downstream transformations. The resulting protected amino acid derivative can be employed to build stereodefined peptide fragments and to prepare C-terminally modified intermediates for further synthesis.

2. Peptide Synthesis Building Blocks

Bzl-L-Ile-OMe*HCl is suitable for peptide building block preparation and fragment coupling strategies used in peptide chemistry. The L-isoleucine backbone provides the α-amino acid stereochemistry and the hydrophobic side chain that participates in sequence-specific peptide conformations, while the benzyl-protected nitrogen supports amide bond formation without uncontrolled side reactions. The methyl ester can be activated or converted to coupling-ready carboxyl equivalents to enable stepwise assembly of protected peptide segments, with the N-benzyl group acting as a removable protection element for later deprotection and chain extension. The compound therefore functions as a chiral intermediate for constructing Ile-containing peptides and peptide analogs with defined protecting-group patterns.

3. Chiral Intermediate Manufacturing

Bzl-L-Ile-OMe*HCl can be applied as a chiral amino acid intermediate in process chemistry intermediate preparation for fine chemical synthesis. The presence of a single stereocenter with L-configuration allows stereochemically consistent downstream incorporation into peptide building blocks and chiral fragments, while the benzyl-protected amine and methyl ester provide stable functional handles for controlled conversion sequences. The hydrochloride salt form supports practical manufacturing considerations such as improved handling of the amine functionality and predictable salt behavior during isolation and intermediate storage. The compound's protected structure aligns with industrial routes that require repeatable protection strategies and predictable transformation of amino acid esters into coupling partners.

4. Side-Chain Functionalization Studies

Bzl-L-Ile-OMe*HCl supports amino acid derivatization and side-chain functionalization research where the branched isoleucine motif is retained as a hydrophobic recognition element. The ester and N-protected amine allow selective transformations to be planned around the side chain, while the protected backbone can be maintained to prevent premature amide formation or undesired coupling during modification steps. The benzyl-protected nitrogen can be retained during side-chain derivatization and later removed to expose the amine for conjugation or peptide incorporation, enabling controlled generation of Ile-modified analogs. The resulting derivatives can serve as defined stereochemical inputs for SAR studies, peptidomimetic construction, and chemical biology investigations requiring hydrophobic side-chain variation.

5. Bioconjugation and Chemical Biology

Bzl-L-Ile-OMe*HCl can be utilized in chemical biology workflows that require incorporation of an Ile-based protected amino acid fragment into larger biomolecule-reactive constructs. The N-benzyl protection and methyl ester provide protected handles that can be transformed into conjugation-ready intermediates, including amine-unmasked forms after deprotection and carboxyl-derived coupling partners after ester activation or conversion. The L-configuration ensures stereochemical fidelity when the Ile fragment is used to probe structure-function relationships in peptide-based ligands, affinity reagents, or labeling scaffolds. The compound thus functions as a stereodefined intermediate for generating biomolecule-modifying reagents and for preparing controlled peptide-like building blocks used in biochemical research.

1. The spatiotemporal control of signalling and trafficking of the GLP-1R

2. Emerging applications of nanotechnology for diagnosis and therapy of disease: a review

3. Myotropic activity and immunolocalization of selected neuropeptides of the burying beetle Nicrophorus vespilloides (Coleoptera: Silphidae)

4. Application of human liver organoids as a patient-derived primary model for HBV infection and related hepatocellular carcinoma

5. TMEM16F and dynamins control expansive plasma membrane reservoirs