Fmoc-D-Lys(Palm)-OH is an Fmoc-protected, D-configured lysine amino acid derivative bearing a side-chain Nε-(palmityl) (Palm) amide substituent, placing it in the class of protected amino acids used for peptide assembly. The molecule contains a free α-amino group and carboxyl group masked for coupling by the Fmoc group on the α-nitrogen while the lysine side chain is modified to a long-chain hydrophobic Nε-acyl functionality, which alters polarity and can influence intramolecular interactions during synthesis. In peptide chemistry, this protected analogue is employed as a building block in stepwise peptide synthesis to introduce an Nε-palmitylated lysine residue for structure-activity studies, lipid-mimetic or hydrophobicity-modulating designs, and preparation of more complex amino acid and peptide derivatives.
CAT No: CP25292
CAS No:1301706-55-7
Chemical Name:N-alpha-(9-Fluorenylmethyloxycarbonyl)-N-epsilon-palmitoyl-D-lysine
Fmoc-D-Lys(Palm)-OH is an Fmoc-protected D-lysine derivative bearing a palmityl (Palm) group on the ε-amino side chain, yielding a long-chain, hydrophobic lysine building block with a stereodefined chiral center at the α-carbon. The molecule contains an N-(9H-fluoren-9-ylmethoxycarbonyl) protecting group on the α-amine, a free carboxylic acid for coupling chemistry, and an ε-N-palmamide that modulates polarity and side-chain reactivity during peptide assembly. The D-configuration supports stereochemical control for unnatural amino acid incorporation and epimerization-sensitive peptide designs, while the amphiphilic balance of the carboxylate and long alkyl side chain can influence aggregation behavior and membrane association. The combination of an orthogonally removable Fmoc group and a stable amide side-chain protection strategy makes the compound a practical amino acid intermediate for peptide building block preparation and downstream synthetic diversification.
1. Peptide Synthesis
Fmoc-D-Lys(Palm)-OH is applied in solid-phase peptide synthesis workflows where the Fmoc-protected α-amine enables standard peptide coupling after base-mediated Fmoc removal. The free C-terminal carboxylic acid participates in amide bond formation, while the ε-N-palmamide functions as a side-chain protection strategy that preserves the lysine ε-position from undesired reactions during chain elongation. The D-stereochemistry can be used to access D-lysine-containing peptide sequences for stereochemically defined analogs that resist proteolytic processing pathways associated with L-amino acid patterns. The long C16 alkyl side chain supports hydrophobic patterning in amphipathic peptides and can be carried through to final products for membrane-interacting peptide materials.
2. Side-Chain Functionalization
Fmoc-D-Lys(Palm)-OH supports amino acid derivatization programs targeting lysine side-chain chemistry where the ε-amide already bears a hydrophobic palmityl handle. The ε-N-palmamide can be leveraged as a controlled, non-nucleophilic lysine surrogate during synthetic steps that require selective reactivity at the α-carboxylate or at other protected positions. The Fmoc group provides orthogonal protection to enable iterative synthesis while deferring side-chain modification until later stages, such as selective deprotection or functional transformation of the lysine-derived scaffold. The resulting long-chain lysine analog can serve as a precursor for amphiphile-like peptide conjugates, lipidated biomolecule fragments, and hydrophobicity-tuned building blocks used in chemical biology and materials-oriented peptide design.
3. Bioconjugation Chemistry
Fmoc-D-Lys(Palm)-OH is suitable for chemical biology and bioconjugation strategies that require lysine-derived linkers with hydrophobic character for controlled association to proteins, nanoparticles, or lipid environments. The protected amino acid format allows incorporation into peptide tags or spacer segments, with the D-configuration enabling stereochemically defined conjugates that can be used to probe recognition and binding effects. The ε-N-palmamide contributes a stable amide-linked alkyl segment that can modulate local microenvironment and influence conjugate solubility and aggregation tendencies during labeling workflows. Downstream, peptide-based conjugates containing this lysine motif can be used as scaffolds for affinity reagents, surface-active probes, and structured linkers in biomolecule modification campaigns.
4. Peptidomimetics And SAR
Fmoc-D-Lys(Palm)-OH is used in peptidomimetic and structure-activity relationship studies where lysine side-chain hydrophobicity and stereochemistry are key variables for molecular recognition. The long alkyl palmyl group provides a tunable hydrophobic element that can be positioned through peptide coupling to generate analog series with controlled steric and lipophilic profiles. The D-lysine stereocenter enables systematic comparison of stereochemical effects on conformational preferences and binding behavior in SAR-oriented molecular design. The Fmoc-protected peptide building block format supports rapid synthesis of analog libraries and subsequent functional group transformations, enabling downstream generation of peptide-like scaffolds for mechanistic studies and binding-site mapping.
5. Pharmaceutical Manufacturing
Fmoc-D-Lys(Palm)-OH can be employed in pharmaceutical manufacturing contexts for the synthesis of protected peptide intermediates used in nonclinical-grade or process development material preparation. The Fmoc-protected α-amine and carboxylic acid functionality align with scalable peptide coupling chemistries, while the ε-N-palmamide provides a stable side-chain protection pattern that can reduce side reactions during iterative assembly. The D-lysine configuration supports manufacturing routes for stereochemically defined peptide analogs where epimerization control and predictable deprotection behavior are required for consistent intermediate quality. The resulting process-compatible amino acid building block can feed into downstream purification and formulation development for peptide-derived ingredients and specialty chemical intermediates.
6. Process Chemistry Intermediate
Fmoc-D-Lys(Palm)-OH serves as a chiral amino acid intermediate for process chemistry and fine chemical synthesis where orthogonal protection and functional-group compatibility guide manufacturing route design. The Fmoc carbamate on the α-amine supports controlled deprotection to reveal the coupling-ready amine, while the palmityl side-chain amide remains intact to maintain the intended lysine substitution pattern through multiple synthetic steps. The presence of a free carboxylic acid enables conversion into activated coupling derivatives or direct peptide coupling inputs, supporting flexible downstream manufacturing operations. The stereodefined D-lysine scaffold and hydrophobic palmyl group can be carried into higher-value peptide building blocks, lipidated fragments, and specialty intermediates used across industrial peptide science and applied amino acid chemistry.
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