Fmoc-Lys(N-Me-Abz-Boc)-OH is an Fmoc-protected lysine derivative bearing a side-chain amine substituted with N-methyl-aminobenzoate (Abz) and a tert-butoxycarbonyl (Boc) group on the remaining nitrogen, classifying it as a protected, non-free amino acid used for peptide-related synthesis. The molecule contains an N-terminal 9H-fluoren-9-ylmethoxycarbonyl (Fmoc) carbamate, a free carboxylic acid at the α-position, and a protected ε-amino functionality on the lysine side chain that includes the Abz substituent and Boc-protected nitrogen, with stereochemistry not specified in the name. In synthesis and labeling workflows, this protected amino acid functions as a stepwise building block for introducing a lysine side chain carrying an Abz motif while maintaining chemoselectivity through orthogonal Fmoc/Boc-type protection, supporting preparation of fluorescent or functionalized peptide analogues for structure-activity and chemical biology studies.
CAT No: CP26866
CAS No:251103-43-2
Synonyms/Alias:Boc-N-Me-Abz-(Fmoc-Lys-OH);ZINC71788123;251103-43-2
Fmoc-Lys(N-Me-Abz-Boc)-OH is an Fmoc-protected lysine derivative bearing a Boc-protected amide-containing side-chain substituent derived from N-methylaminobenzamide (Abz) chemistry. The molecule contains a chiral lysine backbone with an Fmoc carbamate on the alpha-amino group and a protected ε-amino functionality on the side chain, enabling controlled peptide coupling while preventing premature side reactions. The Abz moiety provides an aromatic amide handle that can participate in spectroscopic readouts, while the Boc group supports orthogonal deprotection strategies during stepwise synthesis. The overall structure is engineered for solid-phase peptide synthesis compatibility and downstream conversion into labeled or constrained lysine-containing peptide analogs.
1. Peptide Synthesis
Fmoc-Lys(N-Me-Abz-Boc)-OH supports peptide building block preparation for solid-phase peptide synthesis workflows where lysine side-chain protection and aromatic labeling are required in the same residue. The Fmoc group enables standard base-mediated N-deprotection to expose the alpha-amine for coupling, while the Boc-protected side-chain nitrogen maintains orthogonality to typical Fmoc removal conditions. The N-Me-Abz-Boc side-chain architecture introduces an aromatic amide motif that can be retained through peptide assembly and used as a functional reporter within peptide sequences. Lysine's ε-functionalization pattern allows incorporation into peptides that require defined charge distribution and non-native aromatic features for sequence-dependent studies. The resulting peptidic products can be used as research-grade intermediates for mapping residue effects, generating labeled analog libraries, and preparing sequence-defined materials.
2. Chemical Biology Labeling
Fmoc-Lys(N-Me-Abz-Boc)-OH is suitable for chemical biology research that relies on amino acid derivatization to introduce a defined aromatic amide reporter into biomolecular constructs. The Abz-derived aromatic amide functionality can be positioned at lysine side-chain depth within peptides, enabling monitoring approaches that depend on local environment sensitivity and fixed stereochemical placement. The protected amine and carbamate pattern supports controlled incorporation during peptide synthesis, after which deprotection and side-chain handling can be applied to generate conjugation-ready peptide intermediates. The N-methyl substitution on the Abz unit can modulate hydrogen-bonding and conformational preferences, which may influence how labeled peptides interact with proteins or receptors in vitro. The compound therefore functions as a chiral, residue-specific handle for constructing labeled biomolecule analogs and for probing molecular recognition with defined structural features.
3. Peptidomimetic Construction
Fmoc-Lys(N-Me-Abz-Boc)-OH enables peptidomimetic construction by providing a lysine scaffold that can be carried into constrained or modified analogs while preserving peptide-like connectivity. The Fmoc-protected alpha-amino group supports sequential assembly of peptidic backbones, whereas the Boc-protected side-chain amide-bearing substituent maintains stability during coupling and cleavage steps typical of protected amino acid chemistry. The aromatic Abz motif can be used as a structural element to tune hydrophobicity, aromatic stacking propensity, and local electronic properties within peptidomimetic frameworks. The N-methyl amide character can reduce conformational flexibility relative to unsubstituted amides, which may help generate analogs with improved structural definition for binding studies. The compound can be employed to produce lysine-containing peptidomimetics for structure-guided optimization and for generating analog panels in synthetic organic chemistry.
4. SAR Studies
Fmoc-Lys(N-Me-Abz-Boc)-OH is applicable to structure-activity relationship studies where residue-level modifications at lysine are required to correlate structural changes with measurable experimental outputs. The lysine stereocenter and protected functional groups allow systematic variation of side-chain architecture while keeping the peptide backbone chemistry consistent across a series. The Abz aromatic amide provides a chemically defined substituent that can serve as a reporter element or a physicochemical tuning group, supporting side-chain functionalization strategies that map how aromatic and amide features affect molecular recognition. The orthogonal protection scheme, combining Fmoc and Boc, supports iterative synthesis of analogs with controlled deprotection timing and minimized scrambling or side reactions. The resulting labeled or modified peptides can be used downstream to compare analog behavior in assay formats that depend on sequence-defined chemical structure.
5. Pharmaceutical Manufacturing
Fmoc-Lys(N-Me-Abz-Boc)-OH can be integrated into pharmaceutical manufacturing supply chains for the preparation of labeled or structurally defined peptide intermediates used in process development, analytical method qualification, and reference standard generation. The Fmoc-protected amino functionality supports reproducible peptide coupling chemistry, while the Boc-protected side-chain nitrogen helps maintain consistent impurity profiles by preventing uncontrolled amide/amine cross-reactivity during manufacturing-scale synthesis. The presence of a stable aromatic amide moiety can be advantageous for producing reference materials that retain structural integrity through downstream purification and analytical characterization. The compound's protected amino acid design aligns with industrially relevant orthogonal deprotection strategies used to control stepwise assembly of peptide fragments. The resulting peptides and peptide fragments can be manufactured as defined intermediates for downstream synthetic steps, including conjugation workflows and analytical reference preparation.
6. Analytical Research
Fmoc-Lys(N-Me-Abz-Boc)-OH is suitable for analytical research applications that require incorporation of a defined aromatic amide motif into peptide standards or calibration materials. The Abz-derived aromatic amide can provide a consistent spectroscopic or chromatographic signature when positioned at a lysine side-chain site within a peptide context. The Fmoc/Boc protection pattern enables synthesis of well-defined labeled peptides with controlled residue placement, supporting reproducible analytical readouts across batches of reference compounds. The N-methyl amide feature can influence ionization behavior and fragmentation patterns, which may aid method development for mass spectrometry-based characterization of peptide analogs. The compound can therefore serve as a chiral, residue-specific intermediate for generating analytical standards, method development samples, and structural probes in amino acid and peptide chemistry workflows.
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