D-3-Thiolnorleucine is a D-configured, non-proteinogenic amino acid featuring an aliphatic side chain terminating in a thiol group at the 3-position relative to the α-carbon, with free amino and carboxyl functionalities. The molecule bears a stereogenic center at the α-carbon (D-configuration as indicated by the name) and a reactive sulfhydryl moiety that can undergo thiol-disulfide exchange or be derivatized for controlled conjugation, while the amino and carboxyl groups support acid-base behavior and peptide-coupling chemistry. In biochemical and synthetic workflows, it is used as a building block for incorporating thiol-bearing residues into peptide analogues and for preparing labeled or crosslinkable amino acid derivatives used in chemical biology, protein-structure studies, and structure-activity investigations.
CAT No: CP09302
D-3-Thiolnorleucine is a D-configured thioether-bearing amino acid derivative featuring a chiral α-center and a side chain that terminates in a sulfur functionality suitable for thioalkylation, oxidation-state tuning, and nucleophilic reactivity. The molecule contains the amino acid backbone with a free or derivatizable amino group and a carboxyl group, enabling conversion into protected amino acid forms and subsequent peptide coupling chemistry. The D stereochemistry supports stereochemically defined incorporation into peptide sequences and chiral SAR scaffolds where side-chain orientation influences conformational preferences and recognition. The sulfur-containing side chain can participate in redox transformations and can be functionalized to generate downstream thioether, sulfoxide/sulfone, or thioester-like motifs used in synthetic intermediate design.
1. Peptide Synthesis
D-3-Thiolnorleucine supports peptide building workflows in chemical peptide synthesis by providing a D-configured amino acid backbone with a side-chain sulfur handle that can be preserved or selectively transformed during coupling. The amino and carboxyl functionality enables standard N-protection and C-terminal activation strategies so the residue can be incorporated at defined positions using peptide coupling reagents compatible with thioether-bearing side chains. The stereochemical integrity of the D α-center helps maintain sequence-level stereocontrol, which is relevant for peptidomimetics and constrained analogs where sulfur side-chain geometry affects backbone torsion and intramolecular contacts. The resulting D-thiolnorleucine-containing peptides can be used as research-grade intermediates for further side-chain derivatization and for generating libraries of sulfur-functional peptide analogs.
2. Amino Acid Derivatization
D-3-Thiolnorleucine is well suited for amino acid derivatization and sulfur chemistry intermediate preparation because the side-chain thiol or thioether functionality enables targeted functional group transformations without altering the α-chiral center. The sulfur group can be employed for selective alkylation to introduce thioether substituents, for oxidation to sulfoxide or sulfone analogs to modulate polarity, and for conversion into activated sulfur intermediates for downstream conjugation chemistry. The amino acid backbone can be protected as needed to control chemoselectivity during multi-step syntheses, allowing orthogonal handling of the carboxyl and amino functionalities. The resulting derivatives serve as chiral building blocks for fine chemical synthesis, including preparation of thio-functional linkers and stereochemically defined amino acid reagents used in subsequent coupling or labeling steps.
3. Chemical Biology Labeling
D-3-Thiolnorleucine enables chemical biology workflows that require sulfur-reactive amino acid components for biomolecule labeling and probe construction. The sulfur functionality can participate in nucleophilic conjugation strategies to attach the amino acid residue to electrophilic partners, while the D stereochemistry supports incorporation into peptide-based probes with defined chiral presentation. The amino acid framework supports conversion into protected intermediates for controlled synthesis of peptide tags, affinity handles, or recognition elements that retain the sulfur group for later conjugation. Downstream use can include generation of labeled peptide fragments and chiral chemical tools for studying molecular interactions, binding-site preferences, and structure-dependent reactivity patterns in amino acid-containing constructs.
4. Peptidomimetics And SAR
D-3-Thiolnorleucine is applicable to peptidomimetic construction and structure-activity relationship studies because its D configuration and sulfur side chain provide a stereochemically defined substitution pattern distinct from L analogs. The side-chain sulfur can be used to tune hydrophobicity, polarizability, and potential oxidation-state-dependent behavior, supporting systematic SAR exploration of how sulfur identity and stereochemistry influence conformational bias and molecular recognition. The amino acid can be incorporated into constrained scaffolds through peptide coupling chemistry, then further functionalized to generate a panel of analogs with controlled side-chain electronics and steric profiles. The resulting sulfur-containing D-amino acid motifs can function as chiral SAR elements in medicinal chemistry and chemical biology research intermediate programs.
5. Pharmaceutical Manufacturing Intermediates
D-3-Thiolnorleucine can be integrated into pharmaceutical intermediate preparation and process chemistry routes where stereodefined sulfur-containing amino acid residues are required for downstream synthesis of peptide-like or peptidomimetic intermediates. The compound's amino acid functionality supports conversion into N-protected forms and controlled activation of the carboxyl group for coupling steps in multi-residue assemblies, while the sulfur side chain can be managed through protection, selective oxidation, or chemoselective derivatization depending on the manufacturing sequence. The D stereochemistry supports reproducible incorporation into chiral intermediates used for consistent downstream product profiles in fine chemical production. The sulfur-bearing residue can also serve as a precursor for generating activated sulfur derivatives used in subsequent conjugation or functional group interconversion steps within industrial synthetic planning.
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