D-3-Thiolisoleucine is a D-configured, non-proteinogenic amino acid featuring an isoleucine-derived carbon skeleton bearing a thioether-containing side chain (thiolisoleucine). The molecule contains both an amino group and a carboxyl group, with the side chain presenting a sulfur-containing functionality that can participate in thioether-based chemical transformations and provides distinct polarity and steric characteristics relative to canonical aliphatic residues. In peptide and chemical biology research, D-3-Thiolisoleucine is used as a structurally modified amino acid building block for preparing analog peptides and structure-activity studies, as well as for incorporating a sulfur-containing handle into synthetic targets for subsequent derivatization or analytical labeling.
CAT No: CP09403
D-3-Thiolisoleucine is a chiral D-amino acid derivative in which the side chain bears a thioether functionality at the 3-position, corresponding to a thiol-protected motif that can participate in sulfur chemistry without requiring free thiol handling during early synthetic steps. The molecule contains the amino and carboxyl framework characteristic of amino acid building blocks, enabling conversion to N-protected forms and activation for peptide coupling, while the thioether/thiol-equivalent group influences nucleophilicity, oxidation state control, and downstream functional-group interconversions. Stereochemical definition at the amino acid carbon supports stereospecific incorporation into peptides and chiral intermediate synthesis, and the sulfur-containing side chain can be carried through coupling chemistry with controlled reactivity. D-3-Thiolisoleucine therefore functions as a chemically stable, sulfur-functional amino acid intermediate for peptide science, chemical biology probes, and industrial fine-chemical routes that require a protected thiol surrogate.
1. Peptide Synthesis
D-3-Thiolisoleucine is applied in peptide building-block preparation for solid-phase or solution-phase peptide synthesis where a D-configured sulfur-bearing side chain is required. The amino acid backbone supports N-protection strategies and subsequent activation of the carboxyl group for amide bond formation, while the thioether/thiol-equivalent side chain can be maintained during coupling to reduce side reactions associated with free thiols. Deprotection or side-chain transformation after chain assembly can enable generation of thiol-containing peptide analogs, thioether-to-thiol conversion, or controlled oxidation states for disulfide formation. Incorporation of the D-stereocenter supports stereodefined peptide analogs used in peptide chemistry workflows and structure-function studies of sulfur-containing motifs.
2. Side-Chain Functionalization
D-3-Thiolisoleucine is used for side-chain functionalization in synthetic organic chemistry and biochemical probe development where sulfur chemistry provides a handle for subsequent derivatization. The thioether-bearing 3-substituted side chain can undergo oxidation, alkylation, or conversion to thiol-reactive intermediates under appropriate conditions, enabling access to thioether, sulfoxide, or thiol-based derivatives from a single chiral precursor. The amino acid framework allows selective manipulation through orthogonal protection of the amine and carboxyl groups, supporting downstream formation of amides, esters, or activated intermediates for conjugation. Productive transformation into thiol-bearing or sulfur-functional analogs supports generation of labeling reagents, enzyme-reactive probes, and peptidomimetic fragments with defined stereochemistry.
3. Chemical Biology Probes
D-3-Thiolisoleucine is utilized in chemical biology research for constructing sulfur-functional peptide mimics and labeling substrates that interact with cysteine-reactive or redox-sensitive biochemical environments. The D-amino acid configuration and sulfur side chain enable preparation of stereochemically defined analogs that can be incorporated into peptides used to probe binding pockets, redox pathways, or thiol-dependent recognition events. The protected thiol surrogate behavior helps maintain stability during synthesis and handling, while enabling later release or functional conversion to thiol-reactive forms for conjugation to biomolecules. Downstream formation of bioconjugates and tagged peptide fragments supports analytical and mechanistic studies in applied biochemical research.
4. Bioconjugation Chemistry
D-3-Thiolisoleucine is suitable for bioconjugation workflows where controlled sulfur functionality is required for coupling to proteins, peptides, or polymeric carriers. The amino acid scaffold can be converted to reactive derivatives for conjugation chemistry, while the thioether/thiol-equivalent side chain provides a sulfur anchor that can be transformed into thiol-reactive species or used as a stable linkage element depending on the conjugation strategy. Stereochemical control from the D-center can be maintained through the conjugate synthesis, supporting consistent structure in labeled biomolecular constructs. The resulting sulfur-functional conjugates can serve as intermediates for affinity reagents, immobilized ligands, and analytical standards in biochemical and materials-oriented research.
5. Pharmaceutical Intermediate Preparation
D-3-Thiolisoleucine is applied as a chiral amino acid intermediate in pharmaceutical intermediate preparation and fine chemical synthesis where sulfur-bearing side chains must be introduced with stereochemical fidelity. The amino acid backbone enables conversion to N-protected derivatives and carboxyl-activated intermediates that can be routed into peptide-like fragments, peptidomimetic scaffolds, or sulfur-functional side-chain units. The presence of a protected thiol surrogate reduces handling complexity compared with free thiols during manufacturing-scale synthesis, supporting process-compatible protection and later functional-group unveiling. The compound's defined stereochemistry and sulfur functionality make it suitable for downstream synthesis of chiral, sulfur-containing building blocks used in industrial chemical manufacturing and applied drug-discovery chemistry.
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