Fmoc-L-Orn(Palm)-OH is a protected, naturally occurring amino acid derivative in which L-ornithine bears an Fmoc carbamate on the α-amino group and a Palmityl (Palm) ester protecting group on the side-chain primary amine. The molecule contains a carboxylic acid functionality and two protected nitrogen sites, with the side-chain modified to mask nucleophilicity and modulate chemoselectivity during peptide assembly. In peptide chemistry, it is used as a building block for stepwise incorporation of an ornithine residue into peptides or peptide-related intermediates, where the orthogonal protection pattern supports controlled coupling and side-chain handling.
CAT No: CP25291
CAS No:1301706-41-1
Synonyms/Alias:Fmoc-Orn(palmitoyl);Fmoc-Orn(Palm)
Chemical Name:N-alpha-(9-Fluorenylmethyloxycarbonyl)-N-delta-palmitoyl-L-ornithine
Fmoc-L-Orn(Palm)-OH is an Fmoc-protected L-ornithine derivative bearing a palmityl (Palm) ester on the side-chain, forming a long-chain, lipophilic Nα-Fmoc amino acid building block with a defined stereocenter at the α-carbon. The molecule contains an Fmoc carbamate for orthogonal N-protection during peptide assembly, a free carboxylic acid for C-terminal coupling, and a side-chain ester that can influence solubility, aggregation behavior, and downstream chemoselective transformations. The ornithine scaffold provides a primary amine functionality in the underlying amino acid framework, while the Palm ester masks side-chain reactivity until deprotection or selective functional group manipulation is performed. The combination of chiral amino acid stereochemistry and protected side-chain functionality makes Fmoc-L-Orn(Palm)-OH suitable as a peptide-compatible intermediate and a lipid-modulating chiral precursor in synthetic amino acid chemistry.
1. Peptide Synthesis
Fmoc-L-Orn(Palm)-OH is applied in solid-phase peptide synthesis and peptide fragment construction where Nα-Fmoc protection supports standard Fmoc/tBu-based coupling cycles. The free α-carboxylic acid participates in amide bond formation, while the side-chain Palm ester modulates the ornithine-derived functionality during chain assembly by reducing premature side reactions and altering local polarity around the growing peptide. The long alkyl chain can be used to prepare amphiphilic sequences, lipidated peptide analogs, or membrane-interacting scaffolds after appropriate ester handling. Fmoc-L-Orn(Palm)-OH therefore functions as a chiral, peptide-coupling-ready intermediate for producing ornithine-containing peptides with controlled side-chain protection and downstream lipid functionality.
2. Side-Chain Functionalization
Fmoc-L-Orn(Palm)-OH supports amino acid derivatization strategies that target ornithine side-chain chemistry while maintaining orthogonal protection during synthesis. The Palm ester provides a chemically addressable handle that can be removed or transformed to reveal a side-chain amine equivalent or to enable controlled reinstallation of alternative protecting groups. The resulting side-chain modification pathway can be used to generate cationic ornithine variants, side-chain acylated derivatives, or lipophilic analogs for studying how hydrophobic substitution affects peptide conformation and molecular recognition. Fmoc-L-Orn(Palm)-OH thus serves as a chiral intermediate bridging protected amino acid synthesis and side-chain functional group programming.
3. Bioconjugation Chemistry
Fmoc-L-Orn(Palm)-OH can be employed in chemical biology workflows that require lipid-assisted conjugation or amphiphile tuning of peptide-based constructs. The presence of an Fmoc-protected amino acid backbone enables incorporation into peptide carriers that later undergo side-chain processing to generate reactive amine-containing or lipid-bearing motifs. The Palm ester contributes a hydrophobic segment that may enhance solubility in organic phases, promote self-association, or improve handling of conjugate precursors prior to conjugation steps. Fmoc-L-Orn(Palm)-OH therefore fits into bioconjugation-oriented synthesis of lipid-modified peptides and peptide conjugates used as research reagents and molecular probes.
4. Peptidomimetics And SAR Studies
Fmoc-L-Orn(Palm)-OH is suitable for peptidomimetic construction and structure-activity relationship studies where ornithine-derived cationic character and lipid substitution are treated as tunable structural variables. The Fmoc-protected amino acid format supports systematic replacement of native residues with chiral, side-chain-modified analogs, enabling controlled variation of hydrophobicity and charge presentation along a scaffold. Side-chain Palm ester functionality can be used to generate a family of analogs that differ in acyl chain length or ester stability, supporting comparative studies of how these parameters influence peptide behavior in solution and in binding assays. Fmoc-L-Orn(Palm)-OH thus serves as a chemically defined building block for SAR-driven analog libraries and mechanistic studies in amino acid and peptide science.
5. Pharmaceutical Intermediate Preparation
Fmoc-L-Orn(Palm)-OH is relevant to pharmaceutical intermediate preparation and fine chemical synthesis routes that require protected, chiral amino acid building blocks for downstream manufacturing of peptide-like intermediates. The orthogonally protected Nα-Fmoc group supports controlled deprotection timing relative to coupling operations, while the Palm ester provides a protected side-chain functionality that can be carried through multi-step sequences before conversion to the desired functional form. The defined stereochemistry at the α-carbon supports consistent incorporation into peptide intermediates used for process development and scale-up of peptide-derived chemical entities. Fmoc-L-Orn(Palm)-OH therefore functions as a process-compatible amino acid derivative for industrial synthesis planning where protection strategy and functional group stability are central considerations.
6. Analytical Research Standards
Fmoc-L-Orn(Palm)-OH can be utilized in analytical research for method development and reference standard preparation involving Fmoc-protected amino acids and lipid-modified ornithine derivatives. The combination of an Fmoc chromophore and a long-chain ester yields characteristic chromatographic and spectrometric signatures that can support LC-MS or HPLC method tuning for protected amino acid intermediates. Side-chain Palm ester content enables targeted monitoring of protection/deprotection steps and verification of intermediate identity during peptide building block preparation. Fmoc-L-Orn(Palm)-OH thus serves as a chemically defined standard material supporting analytical characterization workflows in amino acid chemistry and peptide manufacturing development.
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