Boc-D-methionine is a protected amino acid derivative of D-methionine in which the α-amino group is carbamated with a Boc (tert-butoxycarbonyl) protecting group, yielding a methionine side chain featuring a thioether (-CH2-CH2-S-CH3). The molecule contains a free carboxylic acid functional group and a stereogenic center consistent with the D configuration indicated by the product name, while the Boc group suppresses side reactions at nitrogen during coupling chemistry. Boc-D-methionine is used as a stepwise building block in peptide synthesis workflows, including solid-phase or solution-phase strategies, where N-protection supports chemoselective formation of peptide bonds and controlled deprotection of the amino terminus.
CAT No: CP01505
CAS No:5241-66-7
Synonyms/Alias:Boc-D-methionine;N-Boc-D-methionine;5241-66-7;Boc-D-Met-OH;N-(tert-Butoxycarbonyl)-D-methionine;Boc-L-Met-OH;N-(TERT-BUTYLOXYCARBONYL)-D-METHIONINE;(TERT-BUTOXYCARBONYL)-D-METHIONINE;(2R)-2-[(tert-Butoxycarbonyl)amino]-4-(methylsulphonyl)butanoicacid;(2R)-2-[(TERT-BUTOXYCARBONYL)AMINO]-4-(METHYLTHIO)BUTANOICACID;N-tert-Butoxycarbonyl-D-methionine;(R)-BOC-methionine;AmbotzBAA1359;PubChem12201;N-Boc-(D)-methionine;BOC-D-MET;AC1Q5XMH;AC1L38WH;TERT-BUTOXYCARBONYL-D;t-butoxycarbonyl-D-methionine;KSC491O0P;15132_ALDRICH;SCHEMBL1486229;15132_FLUKA;CTK3J1707
Boc-D-methionine is a D-configured methionine building block bearing an N-terminal Boc protecting group, providing a protected amino acid suitable for controlled peptide assembly. With the thioether-containing methionine side chain, it offers compatibility with standard amino acid coupling workflows while maintaining the stereochemical integrity required for D-amino acid incorporation. This protected form is routinely selected when downstream peptide synthesis requires an N-protected residue and a stable, isolable intermediate for custom peptide manufacturing and medicinal chemistry programs.
1. D-Amino Acid Peptide Synthesis
Boc-D-methionine is used by peptide chemists to incorporate D-Met residues into sequence-defined peptides via protected-amino-acid coupling strategies. Its N-Boc protection supports reliable segment assembly in workflows where the N-terminus of the residue must be masked prior to condensation, enabling the construction of D-amino acid-containing peptides for structure-activity relationship studies and backbone stereochemistry control. Researchers developing protease-resistant or stereochemically constrained peptide analogs often select this reagent to introduce the D-configuration at methionine positions while preserving the native thioether side chain for further derivatization or for maintaining sulfur-containing functionality in the final sequence.
2. Medicinal Chemistry Peptidomimetics
Boc-D-methionine serves as a practical methionine-derived intermediate for medicinal chemistry teams preparing peptidomimetics and D-amino-acid enriched analog libraries. The protected Boc format allows integration into custom peptide synthesis routes used to generate series of stereochemically defined compounds for SAR screening, where the position and identity of D-amino acids are key variables. The methionine thioether side chain is particularly useful in programs that require a sulfur-containing residue for maintaining side-chain size and electronic character, or for enabling orthogonal downstream modifications after peptide assembly.
3. Solid-Phase Segment Building
Boc-D-methionine is frequently employed as a protected residue for stepwise peptide assembly workflows, including segment condensation and iterative synthesis strategies that rely on N-protection to manage reactivity. In these workflows, the Boc-protected amino acid is handled as a defined building block to ensure consistent coupling behavior and to support the assembly of peptide fragments that can be further elaborated or combined into longer constructs. Peptide manufacturing groups and academic peptide cores use this reagent when they need a D-methionine-containing segment with a protected N-terminus, reducing variability during fragment preparation and improving traceability in library synthesis.
4. Thioether-Functional Peptide Derivatization
Boc-D-methionine is selected when the methionine thioether side chain must be retained through peptide synthesis and then used as a handle for subsequent chemical modification. After incorporation into a peptide scaffold, the sulfur-containing side chain can be leveraged in downstream derivatization strategies to generate functionalized peptide materials, affinity reagents, or labeled constructs where side-chain chemistry is introduced after sequence assembly. This approach is commonly used in chemical biology and biomaterials research groups that prefer to control modification timing, keeping the residue protected during synthesis while enabling later functional group installation on the thioether-bearing methionine side chain.
1. Urinary Metabolites Associated with Blood Pressure on a Low-or High-Sodium Die
3. C-Peptide replacement therapy and sensory nerve function in type 1 diabetic neuropathy
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