Fmoc-4-amino-1-methylpyrrole-2-carboxylic acid is an Fmoc-protected amino acid derivative featuring a pyrrole ring substituted at the 4-position with an amino group and at the 2-position with a carboxylic acid, with a 1-methyl substituent on the heterocycle. The molecule contains the Fmoc carbamate protecting group on the amino functionality, while the side-chain and ring structure present a heteroaromatic framework that can influence conformational and electronic properties in peptide contexts. In synthesis, it is employed as a building block for solid-phase or solution-phase assembly of peptides and peptide analogues where incorporation of a heteroaromatic, methyl-substituted pyrrolyl residue provides a defined structural handle for structure-activity studies and chemical biology probes.
CAT No: CP26597
CAS No:195387-29-2
Synonyms/Alias:4-(Fmoc-amino)-1-methyl-1H-pyrrole-2-carboxylic acid;195387-29-2;4-(9H-Fluoren-9-ylmethoxycarbonylamino)-1-methyl-1H-pyrrole-2-carboxylic acid;4-(fmoc-amino)-1-methyl-1h-pyrrole-2-carboxylic acid;Fmoc-4-amino-1-methylpyrrole-2-carboxylic acid;1H-Pyrrole-2-carboxylicacid, 4-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-1-methyl-;4-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-1-methyl-1H-pyrrole-2-carboxylic acid;4-(Fmoc-amino)-1-methylpyrrole-2-carboxylic acid;DTXSID90373270;4-(9H-fluoren-9-ylmethoxycarbonylamino)-1-methylpyrrole-2-carboxylic acid;4-({[(9H-FLUOREN-9-YL)METHOXY]CARBONYL}AMINO)-1-METHYL-1H-PYRROLE-2-CARBOXYLIC ACID;fmoc-py-oh;GHRPKWXGCOWBLD-UHFFFAOYSA-N;C21H18N2O4;MFCD02094546;fmoc-nh(4)-mepyl-(2)-oh;SCHEMBL178730;4-(fmoc-amino)-1-methyl-1h-pyrrole-2-carboxlyic acid;DTXCID30324302;Fmoc-NH(4)-MePyl-(2)COOH;AKOS015896185;AC-8727;SB62644;AS-37750;DB-044899;CS-0089844;EN300-1718103;Z1741964537;4-(9-fluorenylmethoxycarbonyl)amino-1-methylpyrrole-2-carboxylic acid;4-[(9-fluorenylmethoxycarbonyl)amino]-1-methyl-2-pyrrole carboxylic acid;4-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-1-methyl-1H-pyrrole-2-carboxylicacid;4-(((9H-fluoren-9-yl)methoxy)carbonylamino)-1-methyl-1H-pyrrole-2-carboxylic acid;822-980-6;
Fmoc-4-amino-1-methylpyrrole-2-carboxylic acid is an Fmoc-protected, non-proteinogenic amino acid building block featuring a 1-methylpyrrole core with a 4-amino substituent and a carboxylic acid at the 2-position. This heteroaromatic side-chain introduces distinct electronic and hydrogen-bonding characteristics that are commonly leveraged in peptide and peptidomimetic design, where conventional aliphatic or aromatic residues are not sufficient to achieve the desired conformation or interaction pattern. The Fmoc group supports standard protected-amino-acid workflows for stepwise peptide assembly, making the compound a practical choice for research-grade synthesis of modified peptide segments and analog libraries.
1. Peptidomimetic Building Block
Fmoc-4-amino-1-methylpyrrole-2-carboxylic acid is used as a heteroaromatic residue in peptide drug discovery and peptidomimetic development, where the 1-methylpyrrole scaffold provides a compact, conformationally informative side chain. Medicinal chemistry groups incorporate this building block into short peptide analogs and scaffold-constrained sequences to probe structure-activity relationships driven by side-chain electronics and hydrogen-bonding capacity. The Fmoc protection enables straightforward integration into custom peptide synthesis workflows, allowing researchers to position the residue at specific sequence locations during analog construction.
2. Solid-Phase Peptide Synthesis
Fmoc-4-amino-1-methylpyrrole-2-carboxylic acid serves as a protected amino acid building block for solid-phase peptide synthesis (SPPS), enabling stepwise incorporation into peptide sequences using established Fmoc deprotection/activation cycles. Peptide synthesis teams use this reagent to generate modified peptides that include a pyrrole-based side chain, supporting rapid library production for screening and downstream biophysical or biochemical characterization. The presence of the Fmoc group supports compatibility with common SPPS strategies, while the carboxylic acid functionality ensures reliable coupling into growing peptide chains.
3. Chemical Biology Probe Peptides
Fmoc-4-amino-1-methylpyrrole-2-carboxylic acid is frequently selected for constructing chemical biology probe peptides that require non-natural heteroaromatic elements to tune local interactions and improve interpretability of labeling or binding studies. Researchers incorporate the pyrrole residue to create probes with distinct physicochemical behavior compared with standard amino acid controls, supporting studies of recognition motifs, peptide-protein interaction mapping, or structure-function experiments where side-chain identity is a key variable. In these workflows, the building block's Fmoc protection supports consistent sequence-level placement, which is essential for comparing probe variants.
4. Structure-Activity Analogue Libraries
Fmoc-4-amino-1-methylpyrrole-2-carboxylic acid is used to expand analogue libraries in medicinal chemistry by introducing a non-natural pyrrole-based residue that can alter hydrogen-bonding patterns and aromatic/heteroaromatic interactions within a peptide framework. Teams developing SAR series rely on this building block to systematically vary sequence composition while keeping the backbone synthesis consistent, enabling controlled comparisons across analogs. The reagent's defined heteroaromatic side-chain functionality makes it a practical choice when researchers aim to evaluate how a specific non-natural residue impacts binding-site geometry and interaction networks in peptide-like scaffolds.
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