N-Me-Thr(Bzl)-OH · HCl is a protected, N-methylated threonine derivative bearing a benzyl (Bzl) ester on the threonine side-chain hydroxyl and a free carboxylic acid, placing it within amino acid derivative and peptide-building-block chemistry rather than an unmodified natural amino acid. The molecule contains an N-methylated amino functionality and a carboxylic acid, and the benzyl ether masks the side-chain alcohol to modulate chemoselectivity during coupling steps, while the HCl indicates formation of a hydrochloride salt to support handling of the basic amine. As a stepwise synthesis intermediate, it is used for preparing modified peptides and amino acid conjugates where controlled side-chain protection, reduced amide-forming reactivity at the nitrogen, and incorporation of a threonine-like motif with a benzyl-protected hydroxyl are required for subsequent deprotection and functional group elaboration.
N-Me-Thr(Bzl)-OH · HCl is a chiral threonine-derived amino acid hydrochloride in which the amino functionality is N-methylated and the side-chain hydroxyl is protected as a benzyl ether, while the carboxyl group remains present for further coupling chemistry. The (Bzl) benzyl protecting group and the N-methyl substitution together modulate nucleophilicity, hydrogen-bonding, and deprotection behavior, supporting controlled peptide assembly and selective functional group transformations. The hydrochloride salt form increases handling stability and solubility in polar media, which can be advantageous for protected amino acid synthesis workflows and downstream derivatization. The stereogenic center inherent to threonine enables stereochemically defined peptide building block preparation and consistent incorporation into peptide and peptidomimetic scaffolds.
1. Protected Amino Acid Synthesis
N-Me-Thr(Bzl)-OH · HCl is used in protected amino acid chemistry as a chiral, N-methylated threonine building block bearing a benzyl-protected side-chain hydroxyl and a free carboxyl handle for activation and coupling. The N-methyl group reduces amine reactivity relative to primary amides, while the benzyl ether protects the hydroxyl from premature acylation during peptide coupling steps, enabling orthogonal protection strategies. The hydrochloride salt form can support reproducible salt-based handling during intermediate preparation and can be compatible with common peptide coupling activation approaches. Downstream, N-Me-Thr(Bzl)-OH · HCl can be converted into activated derivatives for C-terminal or internal residue incorporation, supporting stereodefined peptide construction from amino acid ester or acid activation routes.
2. Peptide Coupling And Fragment Assembly
N-Me-Thr(Bzl)-OH · HCl is applied in peptide synthesis and fragment assembly where a threonine residue with controlled side-chain protection is required for sequential chain elongation. The carboxylic acid functionality participates in peptide bond formation after conversion to an activated coupling form, while the benzyl-protected hydroxyl helps prevent side reactions such as O-acylation or unwanted crosslinking. The N-methylated amino acid motif can be used to introduce N-methyl amide character into peptide backbones, which may influence conformational preferences and proteolytic stability in peptide analogs. The resulting peptide fragments can be carried through iterative coupling and then subjected to benzyl deprotection to regenerate the threonine side-chain hydroxyl for further functionalization or biological assay compatibility.
3. Peptidomimetics And SAR Studies
N-Me-Thr(Bzl)-OH · HCl serves in peptidomimetic construction and structure-activity relationship studies where threonine side-chain geometry and N-methylation are used to tune backbone electronics and hydrogen-bonding patterns. The stereochemically defined threonine center supports consistent spatial presentation of the side-chain hydroxyl after benzyl removal, enabling downstream derivatization such as phosphorylation-mimic formation, etherification, or conjugation handle installation. The benzyl protecting group provides a stable means to carry the hydroxyl through synthetic steps that build peptidomimetic libraries without uncontrolled functional group interference. The hydrochloride salt form can facilitate reproducible intermediate handling for library synthesis workflows that require chiral amino acid inputs with predictable reactivity profiles.
4. Chemical Biology Conjugation Handles
N-Me-Thr(Bzl)-OH · HCl can be employed in chemical biology workflows that require controlled introduction of threonine-derived functional groups into biomolecule-reactive constructs. The protected side-chain hydroxyl allows peptide or linker assembly under conditions that would otherwise risk hydroxyl participation, while subsequent benzyl deprotection can generate a free hydroxyl for controlled derivatization into conjugation-ready motifs. The N-methylated backbone segment can be incorporated into peptide linkers to modulate amide hydrogen-bonding and improve stability of conjugates during purification and storage. The resulting threonine-bearing peptide conjugates can be used as defined probes, standards, or scaffold components for biochemical investigations that depend on precise stereochemistry and functional group placement.
5. Pharmaceutical Intermediate Preparation
N-Me-Thr(Bzl)-OH · HCl is suitable for pharmaceutical intermediate preparation in fine chemical synthesis where protected amino acid building blocks are required for manufacturing-grade peptide-like intermediates. The benzyl-protected hydroxyl provides a robust protection strategy that can withstand common coupling and protecting-group manipulation steps, supporting controlled downstream deprotection to reveal the threonine alcohol when needed for further elaboration. The N-methylated amino acid structure can be used to construct N-methyl amide motifs that are frequently encountered in drug-like peptidomimetic and constrained peptide chemotypes. The hydrochloride salt form supports process-oriented handling of the chiral amino acid input, enabling consistent conversion into activated species for intermediate formation and enabling scalable synthetic routes for peptide-derived or peptide-inspired compounds.
1. An Open-label, Single-center, Safety and Efficacy Study of Eyelash Polygrowth Factor Serum
2. Immune responses to homocitrulline-and citrulline-containing peptides in rheumatoid arthritis
3. Emu oil in combination with other active ingredients for treating skin imperfections
4. Myotropic activity of allatostatins in tenebrionid beetles
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