Fmoc-D-Dap(Aloc)-OH is a protected amino acid derivative based on D-2,3-diaminopropanoic acid (D-Dap) in which the α-amino group is protected with an Fmoc group and the side-chain amino functionality is protected with an Alloc (allyloxycarbonyl) group. The molecule contains both α-amino and α-carboxyl functional groups masked as a carbamate/ester-protected form for chemoselective handling, while the free carboxyl is present as the acid (-COOH) and the stereochemistry is specified as D at the α-carbon. In peptide synthesis workflows, the orthogonal Fmoc/Alloc protection pattern supports stepwise assembly and side-chain functional-group control, while the protected diamino side chain provides a handle for later deprotection and subsequent coupling or conjugation to generate more complex amino acid and peptide derivatives.
CAT No: CP25480
CAS No:178924-05-5
Synonyms/Alias:178924-05-5;(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(((allyloxy)carbonyl)amino)propanoicacid;C22H22N2O6;AmbotzFAA1319;Fmoc-D-Dap(Aloc)-OH;SCHEMBL118389;MolPort-008-267-640;ZINC2572684;6833AH;AKOS022172473;AJ-42067;AK137912;KB-209608;I04-1262;I14-15382;(R)-2-[(9H-Fluoren-9-ylmethoxycarbonyl)amino]-3-[(allyloxycarbonyl)amino]propanoicacid
Chemical Name:N-alpha-(9-Fluorenylmethyloxycarbonyl)-N-beta-allyloxycarbonyl-D-2,3-diaminopropionic acid
Fmoc-D-Dap(Aloc)-OH is an Fmoc-protected, D-configuration amino acid derivative of diaminopropionic acid bearing an allyl oxycarbonyl (Aloc) protecting group on the side-chain amine. The molecule contains an N-Fmoc carbamate that supports base-stable peptide coupling compatibility, while the D stereocenter and the orthogonally protected side-chain enable controlled sequential deprotection and functionalization. The carboxylic acid at the C-terminus is suitable for standard peptide coupling chemistry, and the protected side-chain amine can be unmasked under orthogonal conditions to generate a reactive primary amine for subsequent conjugation or further derivatization. The combination of orthogonal protecting groups and defined stereochemistry makes Fmoc-D-Dap(Aloc)-OH a chiral, peptide-ready intermediate for building side-chain functional motifs in peptide and peptidomimetic scaffolds.
1. Peptide Synthesis
Fmoc-D-Dap(Aloc)-OH is applied in Fmoc-based solid-phase peptide synthesis where the N-Fmoc group controls N-terminal activation and coupling steps while the carboxylic acid participates as the C-terminal reactive handle. The D-configuration at the amino acid backbone supports incorporation of stereochemically defined diaminopropionic residues into peptides, including sequences designed to probe stereochemical effects on binding or stability. The Aloc-protected side-chain amine remains masked during routine peptide assembly, enabling orthogonal deprotection after chain elongation to introduce side-chain conjugation points. Downstream peptide analogs can then be generated for structure-activity relationship studies, chemical biology probes, and scaffold diversification where controlled access to the side-chain primary amine is required.
2. Amino Acid Derivatization
Fmoc-D-Dap(Aloc)-OH supports amino acid derivatization workflows that rely on orthogonal protection of both the backbone nitrogen and the side-chain amine. The Fmoc carbamate provides a removable N-protecting strategy compatible with peptide chemistry, while the Aloc group allows selective side-chain unmasking to generate a primary amine for nucleophilic functional group installation. The resulting free amine can be used to form amide, urea, sulfonamide, or carbamate linkages with activated electrophiles, enabling generation of N- and side-chain-modified derivatives for synthetic methodology development. The stereodefined D-diaminopropionic framework also enables chiral intermediate preparation for downstream medicinal chemistry and materials-facing linker design.
3. Bioconjugation Chemistry
Fmoc-D-Dap(Aloc)-OH is suitable for bioconjugation chemistry where a protected diaminopropionic residue is incorporated into peptide carriers before selective side-chain activation. The orthogonal protecting-group pattern enables sequential unveiling of the side-chain primary amine after peptide assembly, allowing targeted attachment to biomolecule-reactive handles such as activated esters, isothiocyanates, aldehydes, or sulfonylating reagents. The D stereochemistry and the spatially defined side-chain position can be leveraged to tune conjugation geometry in peptide-based linkers, which may influence labeling density and conjugate stability. Conjugation products derived from this intermediate can serve as tools for biochemical research intermediate preparation, including affinity probes, labeling reagents, and modular peptide conjugates.
4. Peptidomimetics And Linkers
Fmoc-D-Dap(Aloc)-OH is used in peptidomimetic and linker construction where the diaminopropionic side chain provides a controlled cationic or hydrogen-bonding element after orthogonal deprotection. The protected primary amine can be transformed into constrained or functionalized motifs that mimic charged residues or serve as attachment points for cyclization, crosslinking, or multivalent scaffold assembly. The Fmoc-protected backbone supports iterative synthesis of analogs and fragment coupling strategies that maintain stereochemical integrity of the D-amino acid unit. Generated peptidomimetic building blocks and side-chain-functionalized intermediates can be applied in molecular design programs and SAR studies focused on backbone and side-chain recognition features.
5. Pharmaceutical Manufacturing
Fmoc-D-Dap(Aloc)-OH can be incorporated into manufacturing-oriented workflows for peptide and peptide-like intermediates where orthogonally protected amino acid building blocks streamline controlled functionalization. The N-Fmoc protection strategy aligns with scalable Fmoc/tethered assembly logic, while the Aloc-protected side-chain amine supports a defined deprotection window for installing functional groups after peptide construction. The presence of a carboxylic acid enables compatibility with activated ester or coupling reagent-based peptide bond formation steps used in fine chemical synthesis and process chemistry. Downstream, the resulting protected or partially deprotected peptide intermediates can be directed toward defined conjugation handles, impurity-controlled synthetic branching, and reproducible intermediate generation for industrial peptide manufacturing routes.
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