Fmoc-D-3-Aminobutyric acid is a protected amino acid derivative featuring a D-configured 3-aminobutyric acid backbone bearing a side chain with an additional methylene relative to alanine. The molecule includes a fluorenylmethoxycarbonyl (Fmoc) protecting group on the α-amino functionality, leaving the carboxyl group and the side-chain primary amine available for controlled chemoselective transformations during peptide construction. In solid-phase or solution-phase peptide synthesis and related amide-coupling chemistry, it functions as a building block that introduces a protected α-amino group while providing a side-chain amino handle for further derivatization, conjugation, or structure-activity studies.
CAT No: CP03008
Fmoc-D-3-Aminobutyric acid is a D-configured, Fmoc-protected amino acid derivative featuring a chiral center at the alpha carbon and a primary amine in the side chain at the 3-position. The molecule contains an N-(9H-fluoren-9-ylmethoxycarbonyl) carbamate that suppresses side reactions during peptide coupling while enabling orthogonal deprotection under standard Fmoc strategies. The free side-chain amino functionality can participate in nucleophilic acylation, sulfonylation, and reductive amination chemistry, allowing controlled conversion into protected or functionalized variants. As an amino acid ester-free solid building block, it is typically handled as a peptide-compatible chiral intermediate for constructing D-amino acid segments and for generating side-chain-modified peptidomimetics and research probes.
1. Peptide Synthesis
Fmoc-D-3-Aminobutyric acid is used in peptide synthesis workflows to introduce a D-3-aminobutyric acid residue that contributes stereochemical inversion relative to L-analogues. The Fmoc carbamate protects the alpha amine during standard coupling cycles, while the side-chain primary amine enables subsequent intramolecular or intermolecular functionalization steps after incorporation. Side-chain reactivity supports the preparation of protected diamino motifs, branching handles, and amide or urea linkages that can be carried through to longer peptide sequences. Downstream, D-configuration incorporation can be applied to generate peptide fragments and analog libraries for stability-oriented scaffold design and mechanistic studies in amino acid chemistry.
2. Side-Chain Functionalization
Fmoc-D-3-Aminobutyric acid is applied in amino acid derivatization and side-chain functionalization chemistry where the pendant primary amine serves as a targeted nucleophile for installing new chemical features. The chiral backbone and Fmoc-protected alpha nitrogen allow selective transformations that focus on the side chain, including conversion to protected amines, sulfonamides, carbamates, and amide-linked substituents. Functionalized products derived from this building block can be used as intermediates for peptidomimetics, constrained scaffolds, and affinity reagents that require defined spacing and stereochemistry. The resulting derivatives support downstream synthetic routes where side-chain chemistry must be orthogonally controlled relative to the peptide-forming nitrogen.
3. Chemical Biology Probes
Fmoc-D-3-Aminobutyric acid is utilized in chemical biology research to construct D-amino acid-containing peptides and peptide-like probes with controlled amine handles for labeling and conjugation. The presence of a protected alpha amine (Fmoc) supports sequential assembly, while the side-chain primary amine can be converted into electrophiles or protected forms compatible with bioconjugation workflows. D-amino acid incorporation can be leveraged to tune resistance to proteolysis and to modulate molecular recognition in structure-function experiments that rely on non-natural stereochemistry. Probe generation from this chiral intermediate enables downstream preparation of labeled peptides, affinity capture reagents, and chemically defined molecular tools for biochemical investigation.
4. Peptidomimetics And SAR
Fmoc-D-3-Aminobutyric acid supports peptidomimetic construction and structure-activity relationship studies through its combination of a stereodefined D-alpha center and a side-chain primary amine for systematic substitution. The Fmoc-protected nitrogen allows reliable peptide coupling to generate analog series, while side-chain derivatization enables rapid generation of amide, urea, heteroatom-rich, or charged variants. The resulting D-3-aminobutyric acid motifs can be used to probe how spacing, hydrogen-bonding capacity, and stereochemical configuration influence binding or conformational preferences in medicinal chemistry contexts. SAR-focused libraries prepared from this intermediate can feed iterative fragment optimization and scaffold refinement using amino acid chemistry-compatible synthetic logic.
5. Process Chemistry Intermediate
Fmoc-D-3-Aminobutyric acid is suitable for process chemistry and fine chemical synthesis as a chiral, Fmoc-protected amino acid intermediate that aligns with scalable peptide-manufacturing strategies. The Fmoc carbamate provides a stable protection mode for the alpha amine during handling and coupling, while the side-chain primary amine enables controlled downstream conversion to protected forms needed for consistent manufacturing of longer sequences. D-configuration and the defined 3-aminobutyl topology support reproducible incorporation into peptide building blocks used in industrial and research-grade synthesis. The compound can therefore be employed as a manufacturing input for producing protected amino acid derivatives, intermediate fragments, and standardized chiral components for peptide and peptidomimetic production.
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