Boc-S-trityl-D-Homocysteine is a protected, sulfur-functionalized homocysteine derivative in which the amino group is masked as a Boc carbamate and the thiol is protected as a trityl thioether (S-trityl). The molecule contains a free carboxyl group and a side chain bearing a thioether sulfur, with D stereochemistry indicated at the α-carbon, while the Boc and trityl groups control chemoselectivity by suppressing undesired amine and thiol reactivity during peptide-coupling steps. In synthetic peptide chemistry and chemical biology workflows, this protected amino acid is used as a stepwise building block to introduce a protected homocysteine residue for subsequent deprotection and downstream functionalization or conjugation studies.
CAT No: CP06307
Boc-S-trityl-D-Homocysteine is a protected D-homocysteine derivative featuring a Boc-protected amino group, a thioether side chain masked as an S-trityl (trityl thioether) group, and a free carboxylic acid suitable for peptide coupling chemistry. The molecule contains a stereogenic center at the alpha carbon consistent with D-configuration, enabling stereochemically defined incorporation into chiral peptide sequences and downstream derivatization. The Boc carbamate and the bulky trityl thioether provide orthogonal protection patterns that can be selectively removed or transformed under controlled conditions, while the carboxylic acid participates in standard amide bond formation. The combination of protected amine, protected sulfur functionality, and maintained chirality makes this compound a practical chiral amino acid intermediate for peptide building block preparation and sulfur-functional synthetic routes.
1. Protected Amino Acid Synthesis
Boc-S-trityl-D-Homocysteine is applied in protected amino acid synthesis workflows where orthogonal protection of the amino and sulfur functionalities is required for controlled peptide coupling. The Boc-protected amine supports predictable N-protection behavior during activation and coupling, while the S-trityl thioether masks the sulfur to mitigate side reactions during peptide assembly and purification. The free carboxylic acid enables conversion to activated esters or coupling reagents that form amide linkages with protected amino partners. Downstream, removal of the Boc group and staged sulfur deprotection can generate D-homocysteine-containing intermediates for peptide building block preparation and chiral intermediate elaboration in fine chemical synthesis.
2. Peptide Synthesis
Boc-S-trityl-D-Homocysteine is used as a peptide building block in solid-phase or solution-phase peptide synthesis targeting sequences that require a D-homocysteine residue. The Boc carbamate and S-trityl thioether provide protection that helps maintain chemoselectivity during iterative peptide coupling steps, limiting undesired sulfur oxidation or thioether participation in side reactions. The D stereocenter is preserved through coupling, supporting stereodefined incorporation for peptide analog construction and stereochemical mapping studies. The resulting peptide products can then be further processed to generate sulfur-unmasked derivatives for subsequent functionalization, enabling structured access to thiol-reactive or sulfur-functional peptide analogs.
3. Side-Chain Functionalization
Boc-S-trityl-D-Homocysteine is suitable for side-chain functionalization programs in amino acid derivatization and sulfur chemistry where controlled exposure of the homocysteine sulfur is needed. The S-trityl group acts as a sterically demanding sulfur protecting group that can be removed to reveal a reactive sulfur handle for further transformations, including conversion to thiol-reactive species or attachment of electrophiles and linkers. The Boc-protected amino group supports selective manipulation of the side-chain without premature amine reactivity, while the carboxylic acid allows formation of amide or ester derivatives that tune solubility and reactivity. The compound therefore serves as a chiral intermediate enabling downstream generation of functionalized sulfur-containing building blocks for chemical biology research and synthetic organic chemistry.
4. Chemical Biology Probes
Boc-S-trityl-D-Homocysteine is applied in chemical biology research where sulfur-containing amino acid analogs are used to construct probes with defined stereochemistry and controlled functional group presentation. The protected sulfur and protected amine allow incorporation into peptide or small-molecule scaffolds while maintaining stability during probe assembly and purification. The D configuration provides a stereochemically distinct residue that can be used to probe molecular recognition, peptide processing, or enzyme selectivity in structure-function studies. After orthogonal deprotection and conjugation steps, sulfur-reactive derivatives derived from this intermediate can be used to generate labeling reagents, affinity handles, or modular probe components for biochemical investigation.
5. Pharmaceutical Intermediate Preparation
Boc-S-trityl-D-Homocysteine is relevant to pharmaceutical intermediate preparation and process chemistry intermediate design for manufacturing routes that require protected sulfur amino acid building blocks. The Boc-protected amine and S-trityl thioether provide a protection strategy that can be integrated into scalable synthesis of chiral intermediates, including activated carboxylic acid derivatives for amide formation. The free carboxylic acid supports conversion into coupling-ready intermediates used to assemble larger fragments under controlled conditions. The stereogenic D-center and orthogonal protection pattern support downstream formation of sulfur-functional motifs used in peptidomimetic construction, fragment elaboration, and fine chemical synthesis where consistent stereochemical identity is maintained.
2. Immune-awakening Saccharomyces-inspired nanocarrier for oral target delivery to lymph and tumors
3. Low bone turnover and low BMD in Down syndrome: effect of intermittent PTH treatment
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