3,5-Dinitro-DL-tyrosine is a non-proteinogenic, aromatic amino acid derivative in which the tyrosine phenolic ring bears two nitro substituents at the 3 and 5 positions, while the molecule retains the amino acid backbone with both an amino group and a carboxyl group. The side chain features a nitro-substituted phenol that can participate in hydrogen-bonding and electrophilic aromatic substitution chemistry, and the "DL" designation indicates a racemic mixture of stereoisomers at the α-carbon rather than a single enantiomer. This compound is used in peptide and protein structure-activity studies and analytical labeling contexts where an electronically modified tyrosine analogue with altered aromatic reactivity and spectroscopic behavior is required for chemical probing or incorporation into synthetic peptide frameworks.
CAT No: CP18403
3,5-Dinitro-DL-tyrosine is a tyrosine-derived aromatic amino acid featuring two nitro substituents at the 3- and 5-positions of the phenolic ring, provided as the DL racemate. The strongly electron-withdrawing nitro groups make this compound a useful, chemically distinctive building block for analytical and synthetic workflows where an unambiguous tyrosine analog is required. Owing to its phenolic and amino functionalities, it is commonly handled as a defined small-molecule reagent for labeling, derivatization, and preparation of nitro-substituted tyrosine standards and intermediates.
1. Analytical Derivatization Standards
3,5-Dinitro-DL-tyrosine is used to prepare derivatized analytical standards and reference materials for methods that distinguish tyrosine-related aromatic motifs by mass and fragmentation behavior. Researchers in analytical chemistry and bioanalytical method development rely on this nitro-substituted tyrosine analog to improve specificity when monitoring aromatic amino acid patterns in complex matrices. The DL configuration supports workflows where stereochemistry is not the primary variable, while the 3,5-dinitro substitution provides a robust chemical "tag" that differentiates it from unlabeled or mono-substituted tyrosine species.
2. Nitro-Tyrosine Intermediate Synthesis
3,5-Dinitro-DL-tyrosine serves as a defined intermediate for downstream synthesis of nitro-substituted aromatic amino acid derivatives and related heteroaromatic building blocks. Organic synthesis teams and pharmaceutical intermediate developers use it to access 3,5-dinitro-phenyl motifs that can be carried into larger scaffolds, including protected or further functionalized tyrosine analogs used in SAR studies and reagent libraries. The presence of both amino and phenolic functionality enables selective downstream conversion into protected amino acid derivatives or phenol-functionalized intermediates, supporting scalable intermediate manufacturing routes.
3. Chemical Biology Labeling Probes
3,5-Dinitro-DL-tyrosine is applied in chemical biology workflows that require a chemically distinctive tyrosine analog for probe construction and controlled derivatization. Investigators use the strongly substituted aromatic ring to create labeling reagents or conjugation-ready derivatives where the nitro pattern provides a spectroscopically or analytically differentiable handle. This compound is particularly useful when a tyrosine-based motif must be tracked or quantified after incorporation into larger chemical constructs, and when stereochemical purity is not required for the readout.
4. Peptide Building Block Derivatives
3,5-Dinitro-DL-tyrosine is used as a starting material to generate nitro-substituted tyrosine building blocks for peptide and peptidomimetic synthesis workflows. Peptide chemistry groups incorporate such aromatic variants to create defined test peptides for method validation, structure-property studies, or reagent development where the 3,5-dinitro substitution alters aromatic electronics and provides a distinct analytical signature. In these applications, the compound's amino acid functionality supports conversion into peptide-compatible forms, enabling its use in constructing tyrosine-containing sequences with a chemically traceable aromatic ring.
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