Fmoc-L-Dap(2-Cl-Z)-OH is an Fmoc-protected amino acid derivative featuring the side chain of L-2,3-diaminopropanoic acid (L-Dap) bearing a 2-chloro-substituted benzyloxycarbonyl (Z) protecting group on one amino functionality. The molecule contains an N-terminal fluorenylmethoxycarbonyl (Fmoc) carbamate, a free carboxylic acid (-COOH), and a stereochemically specified L-center, with the remaining side-chain amino group available for coupling chemistry while the Z group suppresses undesired side reactions. In peptide synthesis workflows, it functions as a protected Dap building block that enables controlled introduction of a diamino side chain under chemoselective conditions and supports preparation of labeled or functionalized peptide analogues for structure-activity and chemical biology studies.
CAT No: CP25227
CAS No:1220955-73-6
Synonyms/Alias:Fmoc-Dapa(Z-2-Cl)-OH;Fmoc-Dpr(Z-2-Cl)-OH;Fmoc-Dap(2-Cl-Z);Fmoc-Dap(2-ClZ);Fmoc-Dap(2-chloro-Z)
Chemical Name:N-alpha-(9-Fluorenylmethyloxycarbonyl)-N-beta-(2-chloro-benzyloxycarbonyl)-L-2,3-diaminopropionic acid
Fmoc-L-Dap(2-Cl-Z)-OH is an Fmoc-protected L-2,3-diaminopropionic acid derivative bearing a side-chain amino group protected as a 2-chloro-benzyloxycarbonyl (2-Cl-Z) carbamate. The molecule combines an N-terminal fluorenylmethyloxycarbonyl (Fmoc) group with a stereodefined L-configuration at the alpha carbon, while the side-chain functionality is masked to control chemoselective peptide coupling. The presence of the 2-chloro substituent on the benzyloxycarbonyl protecting group influences benzyl-type deprotection behavior and supports orthogonal protection strategies relative to other common amino protecting groups. The resulting protected amino acid is engineered for compatibility with standard peptide synthesis workflows and downstream conversion to a diamino acid motif for incorporation into peptide scaffolds and peptidomimetics.
1. Peptide Synthesis
Fmoc-L-Dap(2-Cl-Z)-OH is used as a protected diamino acid building block for solid-phase peptide synthesis where orthogonal protection is required for selective coupling. The Fmoc group enables base-labile N-terminal unmasking, while the 2-Cl-Z carbamate on the side-chain amino group maintains chemoselectivity during chain elongation. The alpha-amino and side-chain amino pattern supports formation of peptide sequences that preserve a controlled diamino functionality for later deprotection and functionalization. The product can be applied to generate protected peptide intermediates that, after orthogonal removal of the side-chain protecting group, yield peptides with reactive amine handles for further derivatization.
2. Side-Chain Functionalization
Fmoc-L-Dap(2-Cl-Z)-OH serves in amino acid derivatization workflows that target controlled introduction of side-chain amine reactivity into peptide or small-molecule frameworks. The protected side-chain carbamate prevents premature side reactions during coupling and purification, while the underlying diamino acid topology supports subsequent conversion to free amines under conditions compatible with peptide-bound substrates. The 2-Cl-Z protecting group design can be leveraged to manage deprotection selectivity when multiple nitrogen functionalities are present in the same synthetic sequence. Downstream use includes preparation of amine-functional peptide analogs for conjugation chemistry, crosslinking studies, or scaffold diversification in synthetic organic chemistry.
3. Chemical Biology Probes
Fmoc-L-Dap(2-Cl-Z)-OH can be incorporated into chemically defined peptide probes used in chemical biology research to study recognition events involving cationic or diamino motifs. The Fmoc-protected amino acid format supports reliable peptide assembly, while the protected side-chain amine allows post-synthetic activation to generate defined charge density and nucleophilicity at a specific position. The stereodefined L-alpha center helps maintain conformational consistency in peptide scaffolds where backbone stereochemistry affects binding and processing. The resulting functionalized peptides can be utilized as research intermediates for assays that require controlled amine presentation for labeling, immobilization, or interaction mapping.
4. Peptidomimetics And SAR
Fmoc-L-Dap(2-Cl-Z)-OH supports peptidomimetic construction and structure-activity relationship studies by enabling systematic variation of diamino acid placement and side-chain reactivity within constrained scaffolds. The protected amine pattern allows iterative synthesis of analog libraries where N-terminal deprotection and side-chain activation can be timed to maintain orthogonality across multiple functional groups. The diamino acid core can be used to introduce hydrogen-bonding and electrostatic features that are often probed during SAR campaigns. The compound's compatibility with peptide coupling chemistry makes it suitable for generating a series of protected intermediates that can be converted into free-amine variants for comparative molecular design.
5. Pharmaceutical Intermediate Preparation
Fmoc-L-Dap(2-Cl-Z)-OH is applicable to pharmaceutical intermediate preparation in fine chemical and specialty manufacturing contexts where protected amino acid building blocks are required for controlled assembly of nitrogen-rich intermediates. The Fmoc group supports standardized N-protection handling in manufacturing-scale peptide or peptidomimetic synthesis, while the 2-Cl-Z side-chain protection helps regulate chemoselective transformations in multi-step routes. The defined stereochemistry and protected diamino functionality can be used to build consistent intermediate profiles for downstream conversion into final active or analytical-stage materials. The compound can therefore function as a process chemistry intermediate for producing protected nitrogen-containing scaffolds used in research and development supply chains.
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