D-Theanine is a D-configured non-proteinogenic amino acid derivative characterized by an ethylamine-linked side chain bearing a γ-glutamyl moiety, placing it within theanine-class compounds used as structural analogs in chemical biology studies. The molecule contains both an amino group and a carboxyl group, enabling it to exist as a zwitterion under aqueous conditions and to participate in standard amino-acid coupling chemistry, while its stereochemistry is specified as D by the product name. D-Theanine is employed in peptide and amino-acid derivative synthesis as a defined chiral building block and in analytical method development and molecular labeling contexts where a non-proteinogenic, stereochemically defined amino acid scaffold is required.
CAT No: CP09102
D-Theanine is a naturally occurring D-configured amino acid derivative featuring an ethylamide side chain linked to a γ-glutamyl framework, with a chiral center at the α-carbon and a secondary amide that can participate in hydrogen bonding and selective acylation chemistry. Theanine contains both a carboxylic acid functionality and an amide-bearing nitrogen, enabling controlled formation of salts, esterification to amino acid esters, and coupling as a protected or activated amino acid building block. The presence of the D-stereochemistry supports stereochemically defined incorporation into peptide-like constructs and chiral analytical workflows, while the polar, zwitterion-forming character influences solubility and downstream formulation behavior. The compound's functional group pattern makes it suitable as a biochemical research intermediate and as a chiral scaffold for derivatization toward N-acylated analogs, labeled standards, and peptide coupling targets.
1. Peptide Coupling Chemistry
D-Theanine is applied in peptide synthesis workflows where amino acid coupling chemistry is required for constructing amide-linked sequences and peptidomimetic fragments. Theanine's α-amino and carboxyl groups can be protected or converted to activated derivatives, while the secondary amide in its side chain can remain intact or be selectively modified depending on the target architecture. D stereochemistry enables stereodefined incorporation when assembling mixed stereochemical peptide analogs, including γ-glutamyl-inspired motifs and constrained turn-forming segments. Downstream, the resulting theanine-containing peptides and analogs can be used as research-grade substrates for method development in peptide coupling and as defined reference materials in structural studies of amino acid sequence effects.
2. Chemical Biology Probes
D-Theanine is utilized in chemical biology research as a chiral, polar amino acid scaffold for generating probe-like derivatives and interaction-mapping tools. Theanine's carboxylic acid and amide functionality support derivatization strategies such as ester-to-amide conversions, N-functionalization for affinity tags, and attachment of reporter handles for binding assays or imaging-compatible analogs. D stereochemistry can be leveraged to probe stereoselective recognition in protein-ligand interactions, enabling comparisons against L-configured analogs in structure-function studies. Labeled or functionalized theanine derivatives produced from this scaffold can serve as biochemical research intermediates for studying amino acid transport, receptor binding, or enzymatic processing pathways at the level of defined chemical structures.
3. Chiral Analytical Standards
D-Theanine is suitable for analytical research where stereochemical discrimination and amino acid profiling require well-defined chiral reference materials. The compound's D configuration and zwitterionic character enable robust use as a calibration standard in chiral chromatography and mass spectrometry workflows, particularly when monitoring amino acid derivatization products. The carboxyl group and secondary amide can also be used to prepare derivatized standards, including esterified or N-acylated forms that improve chromatographic behavior or ionization efficiency. Downstream applications include method validation for amino acid analysis, stereochemical purity checks for peptide intermediates, and development of QA/QC standards for process chemistry intermediates involving theanine-containing building blocks.
4. Process Chemistry Intermediate
D-Theanine is employed in process chemistry and fine chemical synthesis as a chiral amino acid intermediate for manufacturing routes that require controlled stereochemical identity. The compound's functional group set supports scalable transformations such as salt formation, protection/deprotection design for N- or carboxyl-derived derivatives, and conversion to activated intermediates for subsequent coupling steps. The stable amide linkage in the side chain can guide chemoselective protection strategies, allowing predictable downstream formation of peptide building blocks or amide-linked derivatives. Resulting intermediates derived from D-Theanine can be used to streamline the production of theanine-based peptide fragments, labeled reagents, and stereochemically defined amino acid analogs used across biochemical research and industrial chemical manufacturing.
5. Peptidomimetics And SAR Studies
D-Theanine is applied in peptidomimetic design and structure-activity relationship studies where amino acid-derived scaffolds are translated into constrained analogs. Theanine's γ-glutamyl-like connectivity and side-chain amide can be preserved or chemically transformed to tune hydrogen-bonding patterns, conformational preferences, and polarity while maintaining a stereochemically defined chiral center. Carboxyl and amide functionalities enable systematic derivatization for generating libraries of N-substituted, acylated, or C-terminal modified analogs suitable for SAR screening workflows. Downstream, theanine-derived peptidomimetics can serve as research-grade molecular probes that support SAR interpretation through defined stereochemistry and functional group placement, linking amino acid chemistry to measurable structure-dependent behavior in synthetic and biochemical studies.
1. Adipose tissue is a key organ for the beneficial effects of GLP-2 metabolic function
3. Cationic cell-penetrating peptides are potent furin inhibitors
5. Low bone turnover and low BMD in Down syndrome: effect of intermittent PTH treatment
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