D-2-Methylglutamic acid is a D-configured, non-proteinogenic amino acid derivative of the glutamic acid family, featuring a five-carbon side chain with a terminal carboxylate and a methyl substituent at the 2-position relative to the α-carbon. The molecule contains an α-amino group and an α-carboxyl group along with a side-chain carboxylic acid, and the additional methyl substituent modifies steric and polarity characteristics that can influence peptide incorporation and conformational preferences. As a free amino acid building block, it is used in peptide synthesis and structure-activity or labeling studies where a glutamate-like residue with altered side-chain substitution is required to probe chemical properties, backbone/side-chain interactions, or analytical behavior.
CAT No: CP08303
D-2-Methylglutamic acid is a D-configured amino acid featuring a branched 2-methyl stereocenter on the glutamate backbone, with a free α-amino group and a carboxylic acid side chain that can participate in salt formation and amide coupling chemistry. The molecule contains two carboxyl functionalities (α-CO2H and γ-CO2H) whose relative acidity and intramolecular hydrogen-bonding behavior can influence protection strategy selection and downstream peptide coupling conditions. Side-chain branching at C2 introduces steric modulation around the backbone, which can affect conformational preferences in peptidic or peptidomimetic contexts. As a chiral amino acid intermediate, D-2-methylglutamic acid is commonly handled as a protected derivative during synthesis to control chemoselectivity between the α- and side-chain carboxyl groups.
1. Peptide Synthesis
D-2-Methylglutamic acid is applied in peptide building workflows where a D-configured, side-chain carboxyl-bearing residue enables incorporation into peptide chains as a glutamate analog. The amino group and two carboxyl groups support standard peptide coupling logic, while the 2-methyl substituent can bias local sterics and backbone geometry, which is relevant for constructing peptides with altered turn propensity or protease resistance. Protected amino acid chemistry using N-protection and orthogonal carboxyl protection can enable selective amide formation at either the α- or γ-carboxyl direction during sequential assembly. Downstream, the resulting D-2-methylglutamate-containing peptides serve as research-grade substrates for studying stereochemical effects in peptide bond recognition and for generating peptidomimetic scaffolds.
2. Amino Acid Derivatization
D-2-Methylglutamic acid is utilized for amino acid derivatization and chiral intermediate preparation through transformation of its amino and carboxyl functionalities into controlled-reactivity derivatives. Side-chain branching at C2 can be leveraged to tune reactivity in esterification, amidation, and salt formation, supporting the design of intermediates for subsequent functional-group installation. Selective protection of the α-amino and one carboxyl group can facilitate stepwise elaboration, including conversion to activated esters or amide-linked handles for further synthetic elaboration. The resulting derivatives can feed into fine chemical synthesis routes that require stereodefined amino acid fragments for downstream coupling and scaffold diversification.
3. Chiral Synthesis Intermediate
D-2-Methylglutamic acid is suitable as a chiral amino acid intermediate for stereoselective synthesis programs that require D-configuration retention across multistep sequences. The defined stereocenter at C2 and the glutamate-like functional group pattern make the compound a practical feedstock for constructing chiral centers in peptide analogs, constrained ligands, and stereochemically defined building blocks. Orthogonal protection strategies for the α-amino group and carboxyl groups can support controlled deprotection and chemoselective functionalization without racemization at the D-center. The compound's chiral backbone can then be carried forward into higher-complexity syntheses where stereochemical fidelity is required for reproducible structure-function studies.
4. Bioconjugation Chemistry
D-2-Methylglutamic acid can be employed in bioconjugation chemistry where glutamate-like side-chain carboxyl functionality enables attachment or linker design for biomolecule modification. The presence of two carboxyl groups supports the generation of conjugatable forms such as amide-linked or ester-linked handles, while the D-configuration and 2-methyl substitution can influence linker conformation and spacing in conjugates. Protection and selective activation of one carboxyl group can allow controlled coupling to amines or hydrazides on biomolecular partners, supporting site-directed labeling strategies in research settings. Downstream conjugates prepared from D-2-methylglutamic acid derivatives can serve as tools for chemical biology experiments that probe biomolecular interactions with stereochemically defined amino acid motifs.
5. SAR Studies
D-2-Methylglutamic acid is used in structure-activity relationship studies for designing amino acid substitutions that modulate steric bulk and stereochemical presentation within bioactive peptide or peptidomimetic series. The D-configured 2-methyl substitution provides a stereodefined modification relative to canonical glutamate residues, enabling systematic evaluation of how branching and handedness affect binding-site complementarity and conformational behavior. Dual carboxyl functionality supports incorporation into analog libraries where one carboxyl may be used for amide formation while the other remains available for further derivatization or salt-state tuning. The resulting D-2-methylglutamate-containing analogs can be applied as SAR probes in medicinal chemistry workflows focused on optimizing molecular recognition while maintaining controlled synthetic tractability through protected amino acid strategies.
6. Pharmaceutical Intermediate Preparation
D-2-Methylglutamic acid is relevant to pharmaceutical intermediate preparation where stereochemically defined amino acid fragments are required for manufacturing-oriented synthesis of peptide-like or amino acid-derived intermediates. The amino and carboxyl groups allow conversion into protected or activated forms that can be carried into process chemistry routes with predictable chemoselectivity when orthogonal protection is applied. The D-configuration and branched 2-methyl stereocenter can be retained through carefully staged functional group transformations, supporting consistent intermediate identity for downstream coupling steps. Industrially, D-2-methylglutamic acid derivatives can function as chiral building blocks for specialty chemical production, including the preparation of protected amino acid intermediates used in scalable fine chemical synthesis.
1. Peptides as Active Ingredients: A Challenge for Cosmeceutical Industry
4. Immune-awakening Saccharomyces-inspired nanocarrier for oral target delivery to lymph and tumors
5. High fat diet and GLP-1 drugs induce pancreatic injury in mice
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