N-α-Benzyl-D-glutamine methylester hydrochloride is a protected amino acid derivative featuring a glutamine-derived side chain bearing a primary amide, with the α-amino group protected as an N-α-benzyl substituent and the carboxyl group converted to a methyl ester. The molecule is present as a hydrochloride salt, and its D stereochemical configuration at the α-carbon is specified by the product name, while the backbone retains the esterified carboxyl functionality and the side-chain amide provides hydrogen-bonding and polarity for peptide-related studies. In peptide synthesis and chemical biology, this compound is used as a glutamine building block or intermediate, where the N-α benzyl protection and ester form help control chemoselectivity during stepwise assembly or derivatization, and the hydrochloride salt form supports handling of the amino functionality during coupling and downstream transformations.
CAT No: CP00810
N-α-Benzyl-D-glutamine methylester hydrochloride is a D-glutamine-derived amino acid methyl ester bearing an N-α benzyl protecting group and present as a hydrochloride salt, which supports handling of the amino functionality in peptide-coupling workflows. The molecule contains the glutamine side chain amide, a stereogenic center at the D-configuration alpha carbon, and a methyl ester at the carboxyl terminus that can participate in controlled amidation or be converted to other acyl equivalents. Benzyl protection on the α-nitrogen and the salt form together modulate nucleophilicity and chemoselectivity during peptide bond formation and subsequent deprotection steps. The combination of an ester handle, a side-chain amide, and a stable N-protecting group makes the compound a practical chiral intermediate for protected amino acid synthesis and downstream formation of glutamine-containing peptide motifs.
1. Peptide Synthesis
N-α-Benzyl-D-glutamine methylester hydrochloride is used in peptide synthesis as a protected D-glutamine building block where the N-α benzyl group suppresses undesired side reactions during coupling. The methyl ester provides a defined C-terminal functionality that can be activated for amide bond construction or transformed into alternative C-terminal forms depending on the selected peptide assembly strategy. The D-stereochemistry at the alpha carbon supports stereochemically defined incorporation into glutamine-containing sequences, while the side-chain amide can be retained for native glutamine recognition or further functionalized after peptide assembly. The hydrochloride salt form can facilitate consistent reactivity by maintaining the amino group in a controlled protonation state during coupling chemistry. The resulting glutamine-bearing intermediates enable preparation of protected peptide fragments and longer peptide constructs for structural and biochemical studies.
2. Side-Chain Functionalization
N-α-Benzyl-D-glutamine methylester hydrochloride supports side-chain modification chemistry because the glutamine side chain is present as a primary amide that can undergo standard transformations to access derivatives such as activated amide intermediates or protected functional analogs. The N-α benzyl protection helps preserve the alpha-amino functionality while the ester can be selectively manipulated to generate acyl derivatives for subsequent conjugation or derivatization. D-configuration retention enables stereochemically consistent glutamine analogs that may be used to probe amide-mediated interactions in peptide scaffolds. The hydrochloride salt can improve handling and reproducibility when performing stepwise derivatization sequences that require controlled nucleophilicity. Downstream products include functionalized glutamine-containing building blocks suited for peptidomimetic construction and structure-activity relationship studies.
3. Protected Amino Acid Chemistry
N-α-Benzyl-D-glutamine methylester hydrochloride is applied in protected amino acid synthesis as a chiral amino acid ester intermediate where the N-α benzyl group and the ester group provide orthogonal handles for sequential protection, activation, and conversion. The benzyl-protected nitrogen can be removed under appropriate deprotection conditions to regenerate an amino functionality for further coupling, while the methyl ester can be hydrolyzed or transesterified to access carboxylic acid or alternative ester forms. The glutamine side-chain amide remains chemically addressable for controlled derivatization without disrupting the backbone stereocenter. The hydrochloride salt form supports reproducible salt-state management during intermediate preparation and purification steps common to fine chemical synthesis. This makes the compound suitable for manufacturing route design of glutamine-containing peptide building blocks and related chiral intermediates.
4. Chemical Biology And SAR Studies
N-α-Benzyl-D-glutamine methylester hydrochloride is employed in chemical biology workflows to generate D-glutamine-containing peptide analogs for studying amide-dependent recognition and stereochemical effects in biomolecular interactions. The combination of a protected alpha-amino group and a side-chain amide enables incorporation into peptide-like structures while maintaining a defined functional group pattern for downstream analog generation. The methyl ester can serve as a precursor to C-terminal variants that influence solubility, stability, and binding conformations in structure-activity relationship studies. The D-configuration can be used to create stereochemically distinct glutamine residues that help differentiate backbone-dependent versus side-chain-dependent contributions in molecular recognition assays. The resulting derivatives support fragment-based molecular design and SAR investigations focused on peptide and peptidomimetic scaffolds.
5. Pharmaceutical Manufacturing Intermediates
N-α-Benzyl-D-glutamine methylester hydrochloride is relevant to pharmaceutical manufacturing and process chemistry as a controlled, chiral glutamine-derived intermediate for producing protected peptide segments and active-molecule precursors. The presence of a stable N-α protecting group and a methyl ester enables process-compatible conversion to activated acyl forms and subsequent peptide coupling under defined protection schemes. The side-chain amide functionality can be carried through manufacturing sequences as a protected/retained group, reducing the need for extensive protecting-group reshuffling during scale-up. The hydrochloride salt form can support consistent material handling and can be advantageous for reproducible downstream transformations where salt-state affects solubility and reactivity. This intermediate utility aligns with industrial production of glutamine-containing peptides, peptide fragments, and related synthetic intermediates used in applied product development.
2. Cell-based adhesion assays for isolation of snake venom’s integrin antagonists
3. Immune responses to homocitrulline-and citrulline-containing peptides in rheumatoid arthritis
4. Adipose tissue is a key organ for the beneficial effects of GLP-2 metabolic function
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