H-gamma-Carboxy-D-Glu-OH is a free, non-proteinogenic amino acid derivative related to glutamic acid, featuring an additional carboxyl group at the gamma position of the side chain and a terminal primary carboxylic acid on the alpha carbon (α-COOH) along with an amino group (α-NH2). The molecule is specified as the D stereoisomer at the alpha carbon and bears two carboxylate functionalities that can participate in acid-base equilibria and metal-ion coordination, while the gamma-carboxyl group provides a second anionic handle for electrostatic interactions and conjugation chemistry. As a chemically defined dicarboxylated amino acid, it is used as a substrate analog and building block in peptide- and linker-related synthesis, as well as in structure-activity studies and analytical method development where side-chain carboxyl positioning and stereochemistry are relevant.
CAT No: CP27316
CAS No:64153-47-5
Synonyms/Alias:64090-98-8;3-(3-Pyridyl)-L-alanine;(S)-2-Amino-3-(pyridin-3-yl)propanoicacid;L-3-PYRIDYLALANINE;3-(3-Pyridyl)alanine;3'-Aza-L-phenylalanine;(2S)-2-amino-3-(pyridin-3-yl)propanoicacid;3'-PYRIDYL-L-ALA;(S)-2-Amino-3-(3-pyridyl)propionicacid;(2S)-2-amino-3-pyridin-3-ylpropanoicacid;(2S)-2-Amino-3-pyridin-3-yl-propanoicacid;28105-69-3;(2S)-2-AMINO-3-(3-PYRIDYL)PROPANOICACID;3-Aza-D-phenylalanine;3-Aza-L-phenylalanine;3-(Pyridin-3-yl)-D-alanine;3-(Pyridin-3-yl)-L-alanine;DL-3-(3-PYRIDYL)ALANINE;L-3-(3-PYRIDYL)-ALANINE;3-[(2S)-2-Amino-2-carboxyethyl]pyridine;AmbotzHAA1230;(2R)-2-Amino-3-(pyridin-3-yl)propionicacid;beta-(3-Pyridyl)alanine;3-Pyridin-3-yl-L-alanine;3-PYRIDYL-L-ALANINE
H-gamma-Carboxy-D-Glu-OH is a D-configured glutamate-derived amino acid featuring an additional gamma-carboxylic acid on the side chain, yielding a highly polar, dianionic-capable structure under basic conditions. The molecule contains a free alpha-amino group and a free alpha-carboxylic acid, together with the side-chain carboxyl functionality that can participate in salt formation, hydrogen-bonding networks, and metal coordination. The D stereochemistry at the alpha carbon provides defined chiral recognition for peptide coupling and for downstream stereochemical studies. The presence of multiple carboxy groups makes selective protection and controlled deprotection strategies central to its use as a peptide-relevant intermediate and amino acid modification building block.
1. Peptide Synthesis
H-gamma-Carboxy-D-Glu-OH is applied in peptide synthesis and peptide building block preparation where the amino acid backbone supports standard amide bond formation at the alpha-amino position. The compound's side-chain gamma-carboxy group enables incorporation of an additional acidic functionality into peptide scaffolds, supporting peptide coupling chemistry that can be tuned by selective protection of the extra carboxyl group. D stereochemistry can be leveraged to generate stereochemically defined peptide analogs for studying backbone-dependent conformation and recognition. Downstream peptide construction can employ this residue for generating polyacidic segments, for tuning solubility, and for enabling subsequent functional transformations of the side-chain carboxyl group.
2. Amino Acid Derivatization
H-gamma-Carboxy-D-Glu-OH serves as a starting material for amino acid derivatization and functional group transformation strategies that target its multiple carboxylic acids. The gamma-carboxyl group can be selectively esterified, activated, or converted into amide, anhydride, or acyl-transferable derivatives while orthogonal protection of the alpha-carboxyl functionality supports stepwise synthesis. The free amino group can participate in coupling to form protected or unprotected conjugates, including incorporation into larger molecular frameworks for chemical biology and materials-oriented research. The resulting derivatives can act as biochemical research intermediates, chiral building blocks for fine chemical synthesis, or precursors to polyanionic motifs used to modulate solubility and binding behavior.
3. Chemical Biology Probes
H-gamma-Carboxy-D-Glu-OH is suitable for chemical biology research where the strongly acidic side chain can be used to probe electrostatic interactions and binding-site preferences in protein or peptide systems. The D configuration and the extra gamma-carboxyl group provide defined stereochemical and charge-pattern features that can influence molecular recognition during peptide-based assays and ligand design. Protecting-group strategies that temporarily mask carboxyl groups can facilitate conjugation chemistry, followed by controlled deprotection to regenerate the native-like acidic functionality for interaction studies. Downstream use can include construction of peptide mimics and charged ligands that support structure-activity relationship studies and molecular recognition mapping.
4. Protein Engineering
H-gamma-Carboxy-D-Glu-OH can be employed in protein engineering workflows that require incorporation of noncanonical acidic residues into peptide or protein-like constructs. The amino acid's alpha-amino and alpha-carboxyl groups support integration into engineered sequences, while the additional gamma-carboxyl group introduces an extra site for salt-bridge formation and hydrogen-bonding interactions. D stereochemistry allows controlled stereochemical variation relative to L-glutamate analogs, enabling studies of stereochemical effects on folding, stability, and binding interfaces in designed polypeptides. Resulting constructs can serve as research materials for evaluating how expanded acidic side-chain topology affects biomolecular recognition and conformational behavior.
5. Pharmaceutical Intermediate Preparation
H-gamma-Carboxy-D-Glu-OH is relevant to pharmaceutical intermediate preparation within synthetic organic chemistry and process chemistry contexts where chiral, multi-carboxyl amino acid motifs are required. The compound's defined stereocenter and multiple carboxyl groups enable downstream conversion into activated intermediates for forming amide or ester linkages in larger synthetic routes. Selective protection of carboxyl groups supports controlled reactivity during sequential transformations, including preparation of coupling-ready derivatives and controlled functionalization of the gamma-carboxyl group. The resulting intermediates can be used to build peptidomimetic fragments, charged linker units, or stereochemically defined components that integrate into broader manufacturing-oriented synthesis strategies.
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