Fmoc-L-Orn(Mtt)-OH is an Fmoc-protected, L-ornithine-based amino acid derivative bearing an N-Mtt (Mtt = methyltrityl) side-chain protecting group on the ornithine side-chain primary amine. The molecule contains an Fmoc carbamate protecting group on the α-amino function, a free α-carboxylic acid group, and an Mtt-protected ε-amino functionality that modulates chemoselectivity during peptide assembly. In peptide synthesis workflows, it is used as a protected building block that supports stepwise incorporation of ornithine into peptides while controlling orthogonality between the α-amino protection and the side-chain amine protection for subsequent deprotection and functionalization.
CAT No: CP25780
CAS No:343770-23-0
Synonyms/Alias:343770-23-0;Fmoc-(Nd-4-methyltrityl)-L-ornithine;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-((diphenyl(p-tolyl)methyl)amino)pentanoic acid;AmbotzFAA1165;AKOS025286134;ZINC100234337;MFCD00797872;AS-56744;N-alpha-(9-Fluorenylmethyloxycarbonyl)-N-delta-methyltrityl-L-ornithine (Fmoc-L-Orn(Mtt)-OH)
Chemical Name:N-alpha-(9-Fluorenylmethyloxycarbonyl)-N-delta-methyltrityl-L-ornithine
Fmoc-L-Orn(Mtt)-OH is an Fmoc-protected L-ornithine derivative bearing an Mtt (4-methyltrityl) protected side-chain amino group, providing orthogonal protection for peptide and amino acid chemistry. The molecule contains a chiral L-ornithine backbone with a free carboxylic acid suitable for amide bond formation after activation, while the Fmoc group enables base-labile N-deprotection during stepwise solid-phase or solution-phase synthesis. The Mtt-protected side-chain amine is sterically shielded and can be selectively removed under conditions compatible with many peptide workflows, enabling controlled access to the primary amine for further derivatization. The combination of an acid functionality, orthogonally protected amines, and defined stereochemistry makes Fmoc-L-Orn(Mtt)-OH a practical chiral intermediate for constructing polyamine-rich motifs and side-chain functionalized peptide analogs.
1. Peptide Synthesis
Fmoc-L-Orn(Mtt)-OH supports peptide building workflows where orthogonal N- and side-chain protection is required to control coupling order. The Fmoc group protects the alpha-amino functionality during peptide assembly, while the Mtt-protected side-chain primary amine preserves reactivity selectivity until the desired deprotection stage. The free carboxylic acid participates in standard peptide coupling chemistry, enabling incorporation of L-ornithine residues into linear peptides and protected peptide fragments. The resulting ornithine-containing peptide scaffolds can be extended, then selectively functionalized at the side-chain amine to generate cationic or conjugatable sequences for downstream biochemical studies and synthetic methodology development.
2. Side-Chain Functionalization
Fmoc-L-Orn(Mtt)-OH is suited to side-chain derivatization strategies that require masked access to a primary amine on the ornithine side chain. The Mtt group provides a removable protecting element that can be used to generate a controlled window for introducing functional handles such as amide, urea, sulfonamide, or alkylated derivatives. The chiral backbone and preserved stereochemistry help maintain consistent spatial presentation of the side-chain functionality when the amino acid is incorporated into peptides or used as a standalone chiral intermediate. Functionalized ornithine derivatives produced from this scaffold can serve as precursors for charge-tuned analogs, linker-bearing intermediates, and conjugation-ready building blocks in chemical biology and applied peptide chemistry.
3. Bioconjugation Chemistry
Fmoc-L-Orn(Mtt)-OH can be applied to bioconjugation-oriented molecular design where a protected primary amine is needed for controlled attachment chemistry. The orthogonally protected amines allow sequential deprotection and coupling logic, supporting the preparation of peptide conjugates that carry a defined reactive site at the ornithine side chain. The free carboxylic acid and protected amine pattern enable incorporation into peptide carriers, followed by selective side-chain activation for attachment to biomolecule scaffolds, affinity tags, or imaging/assay reagents. Downstream conjugate formation benefits from the predictable reactivity of the generated primary amine, supporting reproducible linker installation for analytical research and molecular interaction studies.
4. Protein Engineering
Fmoc-L-Orn(Mtt)-OH is relevant to protein engineering and engineered peptide/protein fragment construction where incorporation of an ornithine residue can modulate local charge and hydrogen-bonding patterns. The Fmoc-protected alpha-amino group supports controlled residue incorporation, while the Mtt-protected side-chain amine enables later introduction of specific side-chain chemistries without premature cross-reactivity. The chiral L-ornithine framework can be used to build constrained or charge-defined segments that participate in binding interface mapping, epitope mimicry, or scaffold stabilization studies. Resulting engineered constructs can be leveraged to generate structure-defined variants for biochemical investigation, including analog libraries used to probe residue-level effects on molecular recognition.
5. Pharmaceutical Manufacturing
Fmoc-L-Orn(Mtt)-OH fits pharmaceutical intermediate preparation and process chemistry contexts that require orthogonally protected amino acid derivatives for controlled peptide synthesis. The Fmoc group provides a base-labile handle for N-deprotection, while the Mtt side-chain protection supports selective deprotection logic to manage reactive primary amine availability during manufacturing-scale assembly. The presence of a carboxylic acid and protected amines makes the compound compatible with established coupling and protection/deprotection sequences used to generate protected peptide intermediates. Ornithine-containing protected segments derived from this scaffold can serve as inputs for producing peptide-based intermediates and functionalized peptide materials used in industrial fine chemical synthesis and applied manufacturing routes.
6. Analytical Research
Fmoc-L-Orn(Mtt)-OH can be used to prepare defined standards and reference fragments for analytical characterization of peptide products containing ornithine side chains. The orthogonal protection pattern supports synthesis of peptides with controlled placement of side-chain amine functionality, enabling reproducible generation of reference compounds for LC-MS, HPLC method development, and fragmentation pattern assignment. The chiral L-ornithine backbone and protected-group stability during synthesis can help ensure that analytical signals correspond to structurally defined intermediates rather than heterogeneous mixtures. Reference peptides or functionalized ornithine derivatives produced from this compound can support method validation, impurity profiling, and structural verification in research and industrial quality workflows.
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