1-Fmoc-4-(Fmoc-amino)-piperidine-4-carboxylic acid is a protected, non-standard amino acid derivative featuring a piperidine ring bearing a carboxylic acid at the 4-position and an additional amino substituent at the same carbon, with both the ring nitrogen substituent and the side-chain amino functionality protected as fluorenylmethoxycarbonyl (Fmoc) carbamates. The molecule therefore contains a free carboxylic acid group alongside two Fmoc-protected amines, and its stereochemical configuration is not specified in the product name. In peptide chemistry, such bis-Fmoc protected amino acid building blocks are employed to control chemoselectivity during stepwise assembly, enabling orthogonal deprotection and incorporation of the substituted piperidine motif into peptides or peptide-related intermediates for structure-activity studies and chemical biology workflows.
CAT No: CP26869
CAS No:252029-00-8
Synonyms/Alias:252029-00-8;Fmoc-Pip(Fmoc)-OH;1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)piperidine-4-carboxylicacid;1-{[(9H-FLUOREN-9-YL)METHOXY]CARBONYL}-4-({[(9H-FLUOREN-9-YL)METHOXY]CARBONYL}AMINO)PIPERIDINE-4-CARBOXYLICACID;SCHEMBL1404235;CTK4F5199;YCGIGJPLYCPSOP-UHFFFAOYSA-N;C36H32N2O6;6983AH;ZINC71788142;AKOS024464613;CF-1007;AK162677;PL036951;FT-0698099;1,4-Piperidinedicarboxylicacid,4-[[carbonyl]amino]-,1-ester;1,4-Piperidinedicarboxylicacid,4-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-,1-(9H-fluoren-9-ylmethyl)ester;1,4-Piperidinedicarboxylicacid,4-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-,1-(9H-fluoren-9-ylmethyl)ester(9CI);4-(9H-fluoren-9-ylmethoxycarbonylamino)-piperidine-1,4-dicarboxylicacidmono-(9H-fluoren-9-ylmethyl)ester
1-Fmoc-4-(Fmoc-amino)-piperidine-4-carboxylic acid is a piperidine-based, doubly Fmoc-protected amino acid building block designed for peptide and peptidomimetic synthesis. The scaffold incorporates a tertiary amine-containing ring with a carboxylic acid handle and an additional Fmoc-amino substituent, enabling controlled introduction of a conformationally constrained residue during stepwise assembly. Researchers use this compound to access rigidified peptide backbones and to prepare complex, sequence-defined intermediates where orthogonal functionalization is not the primary requirement but double Fmoc activation is advantageous for iterative coupling strategies.
1. Peptidomimetic Backbone Building
1-Fmoc-4-(Fmoc-amino)-piperidine-4-carboxylic acid is used by medicinal chemistry and chemical biology groups to construct conformationally constrained peptide analogs and peptidomimetics. The piperidine core supports backbone rigidity and can help tune local geometry in structure-activity relationship workflows, where analog libraries are synthesized to probe how stereochemistry and side-chain positioning affect binding-relevant conformations. The dual Fmoc functionality supports iterative protection/deprotection-compatible assembly, making it practical for custom peptide synthesis programs that require incorporation of a defined, ring-constrained residue rather than a flexible amino acid analogue.
2. Solid-Phase Peptide Synthesis
1-Fmoc-4-(Fmoc-amino)-piperidine-4-carboxylic acid is a building block for solid-phase peptide synthesis workflows used in academic peptide chemistry labs and peptide manufacturing development. Its Fmoc-protected nature aligns with standard stepwise coupling cycles, enabling incorporation into peptide sequences where a piperidine-containing segment is desired for backbone modulation. The presence of the additional Fmoc-amino substituent supports the preparation of larger, structurally complex intermediates and sequence-defined constructs, including branched or extended motifs that benefit from controlled functional group masking during chain elongation.
3. Complex Intermediate Synthesis
1-Fmoc-4-(Fmoc-amino)-piperidine-4-carboxylic acid is frequently selected for the preparation of advanced peptide fragments and protected intermediates used in segment condensation and custom assembly strategies. The scaffold's protected carboxyl functionality and Fmoc-masked amino substituent help maintain reactivity control during multi-step synthesis, which is valuable when building larger constructs from pre-formed segments. In pharmaceutical intermediate development settings, this compound supports the generation of defined, analytically tractable intermediates that can be carried forward into downstream coupling steps to produce target peptides or peptide-based research reagents.
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