DL-Canavanine sulfate is a non-proteinogenic, basic amino acid analogue featuring an amino acid backbone with a side chain closely related to arginine, bearing a guanidinium-like functionality that is capable of strong ionic interactions. The molecule is provided as the sulfate salt, pairing the protonated basic side chain with sulfate counterions, and the "DL" designation indicates a racemic mixture of stereoisomers at the amino acid stereocenter. In peptide chemistry and chemical biology, canavanine derivatives are used as substrates or structural probes in studies of amino acid recognition and in the synthesis of modified peptides or conjugates where a guanidinium-like side chain and ionic character are required for binding, labeling, or structure-activity investigations.
CAT No: CP04901
DL-Canavanine sulfate is a DL mixture of the amino acid analog canavanine, present as its sulfate salt, featuring a guanidino-like side chain that mimics arginine's charge distribution while altering hydrogen-bonding geometry and steric profile. The molecule contains a free amino group and a carboxylate functionality in salt form, enabling acid-base behavior and salt-mediated handling during synthesis and coupling chemistry. The guanidino-derived functionality is strongly basic and can participate in salt formation, protected-group strategies, and nucleophilic/coordination interactions that influence reactivity in peptide and heterocycle construction. As a chiral amino acid derivative supplied as a racemate, DL-Canavanine sulfate supports stereochemical studies and provides a practical intermediate for downstream derivatization, analytical standards, and amino acid incorporation workflows where enantiomeric composition is controlled at later stages.
1. Peptide Coupling Studies
DL-Canavanine sulfate is applied in peptide synthesis research and method development where guanidino-like side-chain incorporation into peptide backbones is required for studying coupling efficiency and side-chain compatibility. The amino acid backbone provides an amino and carboxylate that can be converted into activated coupling partners, while the strongly basic side chain can be managed through salt formation and orthogonal protection or temporary masking strategies. Racemic stereochemistry enables evaluation of stereochemical effects on amide bond formation and subsequent deprotection or side-chain transformations during peptide assembly. Downstream peptide analogs produced from DL-Canavanine sulfate can serve as substrates for biochemical assays and as structural probes in amino acid chemistry and peptide science.
2. Chemical Biology Probes
DL-Canavanine sulfate is suitable for chemical biology research focused on amino acid analog behavior in protein-associated systems, using its guanidino-like functionality to probe recognition and binding motifs. The sulfate salt form stabilizes the cationic side chain under aqueous and buffered conditions, supporting controlled handling for cell-free labeling workflows and in vitro biochemical investigations. The amino acid analog character enables incorporation into peptide-like structures or conjugation handles after functional group derivatization, supporting studies of molecular recognition, competitive binding, and side-chain-dependent reactivity. Resulting labeled or modified biomolecules can be used as biochemical research intermediates for mapping arginine-mimetic interactions and for constructing chemically defined probes.
3. Unnatural Amino Acid Incorporation
DL-Canavanine sulfate is employed as a racemic unnatural amino acid building block in synthetic biology and protein engineering experiments where guanidino-like side chains are introduced to alter protein properties. The presence of the amino acid backbone supports conversion into activated derivatives for incorporation into peptide chains, while the basic side chain can be tuned through protection/deprotection sequences to match the orthogonality requirements of the chosen assembly strategy. DL stereochemistry supports screening of stereochemical sensitivity in translation-like systems or in chemical ligation contexts, with enantiomeric resolution achievable via downstream separation or chiral derivatization routes. Peptide and protein analogs derived from DL-Canavanine sulfate can function as research materials for structure-function studies and for generating defined amino acid substitutions.
4. Heterocycle And Guanidine Chemistry
DL-Canavanine sulfate is applied in synthetic organic chemistry for guanidine-adjacent transformations and heterocycle construction where the guanidino-like side chain acts as a nucleophilic and coordination-capable functional group. The basic side chain can participate in cyclization or condensation sequences after appropriate functional group adjustment, while the amino acid backbone provides a controllable scaffold for subsequent derivatization into amide, ester, or protected intermediate forms. Sulfate salt handling can influence solubility and reaction medium compatibility, supporting process-friendly preparation of downstream intermediates. Heterocyclic products and functionalized guanidine derivatives generated from DL-Canavanine sulfate can serve as intermediates for medicinal chemistry-like libraries and for materials-oriented building blocks requiring cationic recognition elements.
5. Analytical Standards And Method Development
DL-Canavanine sulfate is used in analytical research as an amino acid reference material for method validation, chiral or achiral quantification development, and mass spectrometric identification of canavanine-like species. The salt form provides consistent ionic character and improves reproducibility in ionization-based workflows, while the racemic composition supports calibration strategies that do not require enantiomeric discrimination. The guanidino-like side chain contributes characteristic fragmentation patterns and strong retention of cationic character, enabling robust identification across chromatographic and spectrometric platforms. Derived standards and labeled or derivatized analogs prepared from DL-Canavanine sulfate can support routine quality control of amino acid derivative synthesis and downstream process monitoring in fine chemical and biochemical research settings.
6. Pharmaceutical Intermediate Preparation
DL-Canavanine sulfate is relevant to pharmaceutical manufacturing and process chemistry as a controlled intermediate for producing guanidino-rich amino acid derivatives and peptidomimetic precursors. The amino acid functional groups allow conversion into protected amino acid derivatives, activated esters, or protected side-chain intermediates that integrate into larger synthetic sequences. The sulfate salt can be leveraged to manage solubility and handling during industrial-scale operations, while racemic supply supports early-stage route development where stereochemical resolution may occur later. Downstream intermediates derived from DL-Canavanine sulfate can feed into specialty chemical production of amino acid analogs, cationic pharmacophore fragments, and peptide science reagents used across applied chemical manufacturing workflows.
2. Store-operated Ca2+ entry sustains the fertilization Ca2+ signal in pig eggs
4. SERS spectrum of the peptide thymosin‐β4 obtained with Ag nanorod substrate
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