1-(Fmoc-aminomethyl)-beta-D-galacturonic acid is an Fmoc-protected amino acid derivative featuring a beta-D-galacturonic acid sugar acid framework bearing an aminomethyl substituent at the 1-position. The molecule contains a carboxylate functionality from the galacturonic acid and a primary amine that is masked as an Fmoc carbamate, providing an orthogonally protected nitrogen handle for peptide-coupling chemistry while the sugar-derived hydroxyl and carboxyl groups contribute multiple hydrogen-bonding and polarity features. In synthesis and chemical biology workflows, this protected, functionalized building block is employed as a precursor for stepwise incorporation of a galacturonic acid-containing motif into peptides or glycopeptide-like conjugates, where the Fmoc group supports controlled amide bond formation and the sugar acid portion supports the introduction of a defined, oxygen-rich side-chain environment.
CAT No: CP27331
CAS No:655246-28-9
Synonyms/Alias:1--beta-D-galacturonicacid;SCHEMBL13437050;ZINC144983210;1-[[(9H-Fluorene-9-ylmethoxycarbonyl)amino]methyl]-1-deoxy-beta-D-galactopyranuronicacid;655246-28-9
1-(Fmoc-aminomethyl)-beta-D-galacturonic acid is an Fmoc-protected amino acid building block featuring a beta-D-galacturonic acid side chain and an aminomethyl handle for incorporation into peptide or glycopeptide-like constructs. The Fmoc group supports standard base-labile protection logic used in modern stepwise peptide assembly, while the uronic acid functionality provides a polar, oxygen-rich stereodefined appendage that is valuable for carbohydrate-mimetic chemistry and solubility tuning in synthetic biomolecules. Researchers commonly select this scaffold when they need a defined, stereochemically consistent galacturonic acid motif presented from an amino acid backbone for downstream conjugation or structure-activity studies.
1. Glycopeptide-Like Assembly
1-(Fmoc-aminomethyl)-beta-D-galacturonic acid is used as a specialized building block in peptide synthesis workflows where a galacturonic acid motif is required as part of a larger sequence. Solid-phase peptide synthesis teams incorporate this residue to generate glycopeptide-like or carbohydrate-functionalized peptides with a stereodefined beta-D-galacturonic acid appendage. The Fmoc protection enables routine stepwise coupling on peptide synthesizers, while the uronic acid side chain contributes strong hydrogen-bonding and a distinct polar surface that can influence folding, recognition, and overall solubility of the resulting synthetic macromolecule.
2. Carbohydrate-Mimetic Conjugates
1-(Fmoc-aminomethyl)-beta-D-galacturonic acid supports chemical biology and medicinal chemistry programs that build carbohydrate-mimetic conjugates for binding studies and structure-function mapping. Synthetic chemists use the galacturonic acid functionality to present an oxygen-rich sugar acid epitope in a controlled orientation relative to a peptide scaffold, often followed by further derivatization of the construct for assay development or immobilization. The aminomethyl linkage provides a convenient synthetic "presentation point" that helps maintain the integrity of the galacturonic acid stereochemistry while enabling modular downstream modification strategies.
3. Uronic-Acid Functional Materials
1-(Fmoc-aminomethyl)-beta-D-galacturonic acid is also applied in biomaterials and surface-functionalization research where uronic-acid-rich interfaces are used to tune hydration, charge density, and specific molecular interactions. Materials scientists incorporate this building block into peptide-based polymers, coatings, or tethered layers to introduce a beta-D-galacturonic acid-containing repeat unit that can enhance water affinity and provide chemically defined functional groups for subsequent coupling steps. The Fmoc-enabled assembly approach is particularly convenient for generating defined constructs that can be transferred into material fabrication workflows while preserving the stereochemical identity of the sugar acid motif.
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