Bz-Met-NH2 is a benzoyl-protected methionine amide, consisting of methionine bearing a benzoyl (Bz) group on the amino functionality and a terminal primary carboxamide (-CONH2) at the carboxyl position. The side chain contains a thioether (-S-CH3) characteristic of methionine, and the molecule retains an amide-linked backbone with the N-acyl benzoyl group acting as a protecting group for chemoselective peptide and amide-bond-forming transformations. As an amino acid amide intermediate, it is used in peptide chemistry and related synthesis to control functional-group reactivity and to introduce a methionine-derived residue into larger peptide or amino-acid-derived structures.
CAT No: CP27182
CAS No:52811-71-9
Synonyms/Alias:52811-71-9;Bz-Met-NH2;AC1ODTM2;Benzoyl-L-methionineamide;SCHEMBL4388419;MolPort-008-267-349;ZINC1640066;CJ-26407;N-[(2S)-1-amino-4-methylsulfanyl-1-oxobutan-2-yl]benzamide
Bz-Met-NH2 (N-(2-phenylacetyl) methionamide) is a methionine-derived primary amide that retains the thioether-containing side chain characteristic of Met, while coupling the α-amino functionality to a benzyl-type acyl group (Bz) that modulates nucleophilicity and controls chemoselective reactivity. The molecule bears a stereogenic α-carbon inherited from L-methionine, enabling stereochemically defined downstream peptide or peptidomimetic assembly. The amide carbonyl and the N-acyl protection strategy reduce undesired side reactions during coupling, while the thioether can participate in selective oxidation or functional-group interconversions to access sulfoxide/sulfone motifs and related sulfur chemistry. As a compact, protected amino acid amide, Bz-Met-NH2 functions as a chiral amino acid derivative and synthetic intermediate for building peptide fragments and sulfur-functionalized analogs in both research and industrial fine-chemical workflows.
1. Peptide Synthesis
Bz-Met-NH2 supports peptide coupling chemistry in peptide building-block workflows because the N-acylated methionamide form provides an amide-stabilized nitrogen that can be carried through fragment assembly with reduced risk of premature N-reactivity. The α-amide/α-carbonyl framework and the protected amide nitrogen align with standard peptide synthesis logic for constructing Met-containing sequences, while the thioether side chain remains chemically addressable for later derivatization. The stereogenic center provides stereochemical fidelity for Met incorporation into oligopeptides and peptidomimetics, including controlled generation of Met analogs after side-chain oxidation. Downstream use can include preparing Met-bearing peptide intermediates, generating defined peptide fragments for structure-activity relationship studies, and supplying chiral inputs for iterative peptide construction in synthetic organic chemistry.
2. Amino Acid Derivatization
Bz-Met-NH2 is suitable for amino acid derivatization strategies that exploit the methionine thioether side chain while maintaining the α-amide scaffold for selective transformations. The thioether can be oxidized to sulfoxide or further to sulfone under controlled conditions, enabling access to stereochemically informative sulfur oxidation states that are frequently used to probe binding interactions and stability in peptide analogs. The N-benzyl-type acyl protection (Bz) and the terminal primary amide functionality enable chemoselective functional-group handling, including orthogonal protection/deprotection sequences when converting the compound into other protected Met derivatives. The resulting sulfur-functionalized products can serve as biochemical research intermediates, peptidomimetic components, and downstream precursors for molecular scaffolds that require tunable polarity and redox-responsive behavior.
3. Chemical Biology Probes
Bz-Met-NH2 can be applied in chemical biology research where Met-containing motifs are used to interrogate protein recognition, redox microenvironments, and side-chain-dependent conformational effects. The preserved methionamide backbone and the thioether side chain enable incorporation into peptide probes that may undergo controlled oxidation to sulfoxide/sulfone forms, supporting studies of how sulfur oxidation state influences molecular interactions. The N-acylated amino acid derivative format helps maintain defined connectivity during probe synthesis and supports conversion into conjugatable intermediates for labeling or affinity-tagging workflows. Downstream applications include preparing Met-based probe fragments for biochemical assays, generating defined peptide analogs for mechanistic studies, and supporting structure-function experiments that rely on stereodefined amino acid chemistry.
4. Protected Amino Acid Chemistry
Bz-Met-NH2 functions as a protected amino acid derivative in synthetic planning because the Bz acyl group on the nitrogen provides a stable, controllable protection element that can be carried through multi-step sequences. The methionamide structure provides an amide-compatible platform for coupling logic, allowing the α-carbon stereocenter and side-chain thioether to be retained while the nitrogen protection strategy governs chemoselectivity. The terminal amide and acyl-protected nitrogen can be leveraged to design orthogonal protection schemes for subsequent conversion into other peptide building blocks, including C-terminal functionalization or further N-protection adjustments. Industrially relevant use includes preparing chiral amino acid intermediates for fine chemical synthesis and supporting manufacturing routes that require reproducible, isolable protected forms for downstream peptide fragment production.
5. Pharmaceutical Intermediate Preparation
Bz-Met-NH2 is applicable to pharmaceutical intermediate preparation where defined Met-containing chiral fragments are required for peptidomimetic and peptide-like scaffold construction. The compound's amino acid amide architecture supports incorporation into larger synthetic sequences that generate drug-discovery libraries, with the thioether side chain providing a handle for controlled oxidation to modulate polarity and metabolic stability proxies in analog design. The N-acyl protection strategy contributes to process-compatible handling by reducing undesired side reactions during intermediate formation and purification steps. Downstream utility can include supplying a stereochemically defined chiral intermediate for manufacturing of peptide analog building blocks, enabling consistent assembly of Met-bearing structures used in medicinal chemistry and applied synthetic methodology.
4. High fat diet and GLP-1 drugs induce pancreatic injury in mice
5. SERS spectrum of the peptide thymosin‐β4 obtained with Ag nanorod substrate
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