Fmoc-L-Dap(Palm)-OH is an Fmoc-protected, L-form amino acid derivative of 2,3-diaminopropanoic acid (L-Dap) bearing a palmityl (Palm) substituent on the side-chain amino group, classifying it as a protected, non-free amino acid used for peptide building blocks. The molecule contains an Fmoc carbamate on the α-amino group and a carboxylic acid at the α-position, while the side-chain functionality is modified from a free primary amine to an N-palmitylated amide-like secondary/tertiary amine environment that changes hydrogen-bonding and lipophilicity relative to unmodified Dap. In synthesis, the orthogonally protected amine and the carboxyl group support stepwise peptide coupling in solid-phase or solution-phase workflows, and the long-chain Palm group can be used to introduce hydrophobic side-chain character for structure-activity studies, membrane-associated peptide designs, or lipidated analog preparation.
CAT No: CP26015
CAS No:724785-41-5
Chemical Name:N-alpha-(9-Fluorenylmethyloxycarbonyl)-N-beta-palmitoyl-L-2,3-diaminopropionic acid
Fmoc-L-Dap(Palm)-OH is an Fmoc-protected, L-configured lysine analog in which the side-chain bears a protected diaminopropyl terminus (Dap) with a Palmityl-type protecting group on the terminal amine. The molecule combines an aromatic fluorenylmethoxycarbonyl group for orthogonal N-protection at the α-amino position with a stereochemically defined chiral center typical of amino acid building blocks, enabling controlled peptide coupling under standard solid-phase or solution-phase conditions. The side-chain functional arrangement presents a protected primary amine that can be selectively deprotected to reveal a nucleophilic handle for subsequent derivatization, crosslinking, or further peptide elaboration. The presence of both a carboxylic acid and protected amine functionality makes the compound a robust intermediate for amino acid derivatization workflows and for constructing peptides that require lysine-like spacing with tunable reactivity.
1. Peptide Synthesis
Fmoc-L-Dap(Palm)-OH is used in peptide synthesis workflows where an Fmoc-protected α-amino group supports stepwise N-terminal deprotection and peptide bond formation while maintaining side-chain protection during chain assembly. The Dap side chain with a Palm-protected terminal amine provides a latent cationic functionality that can be preserved through coupling cycles and then unveiled for downstream modifications or for generating defined amine-containing peptide motifs. The free carboxylic acid enables incorporation as a protected amino acid building block compatible with peptide coupling chemistry, supporting the construction of peptides that require controlled presentation of a lysine-like side chain. The resulting peptide products can be used as research-grade scaffolds for studying amine-dependent interactions, folding behavior, and sequence-specific recognition in biochemical assays.
2. Side-Chain Functionalization
Fmoc-L-Dap(Palm)-OH is suited to chemical modification strategies targeting side-chain amines, particularly where orthogonal protection is needed to control timing of deprotection and functional group installation. The Palm-protected terminal amine can be selectively removed under appropriate conditions to generate a primary amine for conjugation, salt-bridge engineering, or attachment of electrophiles such as activated carbonyls, sulfonyl groups, or bioconjugation-ready handles. The orthogonality between the Fmoc group and the side-chain protecting group supports sequential transformations, allowing selective exposure of the Dap amine without perturbing other functional elements. The liberated amine can then be used to generate amine-functionalized peptide analogs, linkers for biomolecule conjugation, or chemically defined intermediates for further synthetic elaboration.
3. Bioconjugation Chemistry
Fmoc-L-Dap(Palm)-OH serves as an amino acid reagent for bioconjugation and chemical biology applications where controlled incorporation of a protected primary amine improves reproducibility of labeling and conjugate synthesis. The Dap side chain provides an extended amine-bearing motif that can be revealed from the Palm protection to enable coupling to biomolecule-reactive partners, including NHS-activated esters, aldehyde-based linkers, or other electrophiles used for amine targeting. The Fmoc-protected backbone facilitates preparation of peptide conjugation motifs with defined length and spacing, which can influence local charge density and conjugate solubility. Downstream, the resulting amine-bearing peptides or peptide fragments can be employed for creating labeled probes, affinity reagents, or modular conjugates for assays that rely on predictable functional group placement.
4. Peptidomimetics And SAR Studies
Fmoc-L-Dap(Palm)-OH is applicable to peptidomimetic construction and structure-activity relationship studies where lysine-like side-chain topology and controlled amine exposure are used to tune molecular recognition. The stereochemically defined L-Dap scaffold, combined with orthogonal protection, supports the synthesis of analog series in which the side-chain amine is introduced at a specific position and then transformed into alternative functionalities for SAR mapping. The protected amine can be used as a handle for converting the side chain into amide, sulfonamide, urea, or other derivatives that modulate hydrogen-bonding and charge state while retaining the peptide backbone architecture. The ability to generate a sequence-defined set of amine-modified analogs makes the compound compatible with iterative medicinal chemistry workflows focused on mapping how side-chain chemistry affects binding and function in vitro.
5. Pharmaceutical Manufacturing Intermediate
Fmoc-L-Dap(Palm)-OH is relevant to pharmaceutical manufacturing and fine chemical synthesis as a protected amino acid intermediate for producing amine-containing peptide segments used in active ingredient synthesis and process-scale peptide assembly. The Fmoc protection strategy supports controlled N-terminal handling during manufacturing, while the Palm-protected side-chain amine helps manage reactivity during repeated coupling and purification steps. The defined stereochemistry and functional group protection pattern support consistent downstream deprotection and incorporation into longer sequences, which is critical for reproducible peptide composition. The compound can therefore be integrated into industrial peptide building workflows that require reliable protected amino acid inputs for scalable synthesis of protected peptide intermediates and subsequent functionalization steps.
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