L-3-Thiolnorvaline is a non-proteinogenic, sulfur-containing amino acid featuring a branched aliphatic side chain bearing a thiol group at the 3-position relative to the α-carbon, with free amino and carboxyl functional groups in the L stereochemical form. The side-chain thiol provides a reactive handle for redox-dependent chemistry and for forming thioether or disulfide-linked derivatives, while the amino and carboxyl groups enable acid-base behavior and participation in peptide coupling or analytical derivatization. It is used in peptide chemistry and chemical biology workflows to introduce thiol functionality into synthetic peptides or to support structure-activity and labeling studies where a defined sulfur-containing amino acid building block is required.
CAT No: CP09502
L-3-Thiolnorvaline is an L-configured amino acid analog featuring a chiral α-carbon and a side chain terminated by a thiol group, positioned at the 3-position relative to the backbone. The molecule contains a primary amino functionality and a carboxylic acid (or, depending on supplier form, a protected/derivatized acid), enabling standard amino acid coupling chemistry while the free thiol provides redox- and nucleophile-driven reactivity. The sulfur-bearing side chain can participate in thioether formation, disulfide exchange, and selective derivatization to install stable handles for downstream conjugation or analytical detection. As a chiral amino acid intermediate and peptide-relevant building block, L-3-Thiolnorvaline supports stereochemically defined incorporation into peptide frameworks and can be transformed into protected thiol derivatives to manage oxidation during synthetic sequences.
1. Peptide Synthesis
L-3-Thiolnorvaline serves as a peptide building block for assembling thiol-containing sequences used in peptide chemistry and chemical biology research. The α-amino acid backbone supports amide bond formation via standard peptide coupling strategies, while the side-chain thiol can be protected as a thioether or thiol-protecting group to maintain compatibility with coupling and deprotection steps. Incorporation into peptide chains enables access to disulfide-linked analogs, native-like redox motifs, and thiol-functional peptide fragments for subsequent conjugation. Downstream peptide products can be used to probe folding, stability, and site-specific reactivity in amino acid and peptide science workflows.
2. Chemical Biology Conjugation
L-3-Thiolnorvaline functions as an amino acid substrate for bioconjugation chemistry where thiol nucleophilicity and controlled oxidation state are central. The side-chain thiol provides a reactive sulfur center for forming thioether linkages to electrophilic tags, affinity handles, or reporter groups under conditions that preserve the L-stereochemistry at the α-carbon. The amino acid's defined functional groups also support orthogonal derivatization planning, including temporary thiol protection and later deprotection to trigger site-selective coupling. Resulting thiol-bearing conjugates can be applied as molecular probes, labeling intermediates, or chemically defined building blocks for biomolecule modification.
3. Chiral Amino Acid Intermediate
L-3-Thiolnorvaline is suitable as a chiral amino acid intermediate for stereoselective synthesis of sulfur-containing derivatives used in fine chemical production and process chemistry. The L-configuration at the α-carbon enables downstream construction of enantiopure thioether, sulfoxide, and disulfide-related motifs through controlled sulfur functional group transformations. The thiol group can be converted into protected forms to improve handling stability and then reverted to the free thiol for subsequent derivatization steps, supporting robust manufacturing route design. Industrially, the compound can be used to prepare chiral sulfur-containing intermediates that feed into specialty chemicals requiring defined stereochemistry.
4. Side-Chain Functionalization
L-3-Thiolnorvaline supports side-chain functionalization strategies that convert the thiol into chemically distinct sulfur functionalities for SAR studies and synthetic methodology development. The sulfur center can be transformed into thioethers, disulfides, or oxidized derivatives, enabling systematic exploration of how electronic and steric changes at the 3-thiol position affect molecular recognition. The presence of both amino and carboxyl groups allows selective protection schemes that decouple backbone reactivity from thiol chemistry, facilitating stepwise synthesis of functionalized analogs. Generated derivatives can serve as research intermediates for building peptidomimetics, redox-active scaffolds, and thiol-reactive probes.
5. Analytical Research Standards
L-3-Thiolnorvaline can be employed in analytical research as a reference material and derivatization target for quantifying thiol-containing species and monitoring thiol stability. The defined thiol functionality enables formation of detectable derivatives through controlled reaction with thiol-reactive labeling reagents, supporting method development for chromatographic and spectrometric workflows. The amino acid backbone provides a consistent chemical identity for calibration and for validating derivatization selectivity in complex matrices where thiol oxidation may occur. Downstream analytical use includes supporting quality control of thiol-bearing intermediates and peptide fragments during amino acid derivative synthesis and peptide coupling sequences.
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