3-(2-Pyrrolyl)-D-alanine is a D-configured amino acid derivative in which the side chain bears a 2-pyrrolyl (pyrrole) substituent rather than a standard proteinogenic functional group. The molecule contains both an amino group and a carboxyl group on the amino acid backbone, with the pyrrolyl side chain providing an aromatic heterocycle that can participate in hydrogen bonding and π-related interactions while remaining chemically distinct from aliphatic or hydroxyl-bearing residues. It is used in peptide and amino acid derivative synthesis and structure-activity studies to introduce a heteroaromatic handle into amide-linked frameworks, and it can also serve as a defined building block for analytical method development involving pyrrole-containing amino acid motifs.
CAT No: CP23502
3-(2-Pyrrolyl)-D-alanine is a D-configured amino acid bearing a heteroaromatic 2-pyrrolyl substituent at the side chain, making it a useful building block for heteroaryl-containing peptide and peptidomimetic designs. Its combination of an amino acid backbone with a pyrrole-containing functional group supports downstream incorporation into synthetic sequences where aromatic electronics and heterocycle chemistry are desired. Researchers also use this scaffold to introduce a defined heteroaryl motif for structure-activity relationship studies and for chemical biology probes that require a stable, non-proteinogenic aromatic handle.
1. Peptidomimetic Building Block
3-(2-Pyrrolyl)-D-alanine is used by medicinal chemistry and peptide research groups to assemble heteroaryl-substituted peptidomimetics and modified peptide analogs where the D-amino acid stereochemistry and the pyrrolyl side chain help tune conformation and chemical functionality. The heteroaromatic pyrrole unit provides a distinct electronic and hydrogen-bonding environment compared with aliphatic or phenyl side chains, supporting SAR workflows that compare aromatic heterocycles in otherwise matched peptide scaffolds. Synthetic teams commonly select this amino acid when they need a defined, non-natural aromatic residue that can be incorporated into custom peptide sequences during building-block assembly.
2. Heteroaryl Peptide Synthesis
3-(2-Pyrrolyl)-D-alanine serves as a targeted amino acid building block for the preparation of peptides containing a pyrrole-bearing residue, enabling site-specific placement of a heteroaryl motif within a defined sequence. Peptide synthesis teams value the amino acid backbone functionality for straightforward coupling into peptide intermediates, while the pyrrolyl side chain supports the construction of aromatic/heteroaromatic peptide variants used for receptor-binding studies, enzyme substrate mapping, and structure-function experiments. This product is also frequently used when researchers want a non-proteinogenic aromatic side chain that remains chemically well-defined through the synthetic campaign and downstream analytical characterization.
3. Chemical Biology Probe Precursors
3-(2-Pyrrolyl)-D-alanine is employed as a chemical biology precursor for constructing probe-like peptide derivatives that incorporate a pyrrole heterocycle as a recognition or structural element. In practice, researchers use this residue as part of larger synthetic constructs where the heteroaryl substituent contributes to interaction patterns, labeling strategies, or assay readouts that depend on the presence of a defined aromatic heterocycle. By using a D-amino acid building block, probe designers can also introduce stereochemical control into the peptide framework, supporting comparative studies of probe behavior across stereochemical variants and heteroaryl substitutions.
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