Dimethyl ((3S)-4,4-dimethyl-3-(Boc-amino)-2-oxopentyl)phosphonate is a phosphonate-containing amino acid derivative featuring a Boc-protected amino group attached to a 2-oxopentyl backbone with a stereogenic center at C3 specified as (3S). The molecule bears a dimethyl phosphonate moiety as well as a carboxamide-forming Boc group (tert-butoxycarbonyl) and a ketone/oxo functionality at the 2-position, combining an N-protected amine with a carbonyl-bearing chain that can participate in further synthetic elaboration. In research and synthesis, such amino acid-derived phosphonates are employed as phosphoryl-mimetic or chemically stable handles for constructing more complex phosphonate/aminocarbonyl frameworks, including routes to labeled or structure-defined peptide-related intermediates and analytical standards.
CAT No: CP26533
CAS No:176504-89-5
Synonyms/Alias:Dimethyl((3S)-4,4-dimethyl-3-(Boc-amino)-2-oxopentyl)-phosphonate;
Dimethyl ((3S)-4,4-dimethyl-3-(Boc-amino)-2-oxopentyl)phosphonate is a chiral, Boc-protected amino acid derivative in which a phosphonate group is installed at the α-carbon framework and a tert-butoxycarbonyl-protected amine is carried on the side chain. The (3S) stereocenter and the adjacent carbonyl establish a rigid peptide-compatible motif, while the phosphonate functionality provides strong anionic character under deprotonating conditions and enables phosphorylation-mimetic behavior in synthetic and biochemical contexts. The molecule contains a carboxamide-forming carbonyl (as part of the amino acid backbone) and a protected carbamate nitrogen, which together support controlled peptide coupling and orthogonal deprotection strategies. The dimethyl phosphonate can be retained as a protected phosphate equivalent during assembly, then transformed downstream into more reactive or biologically relevant phosphate forms, making the compound a practical chiral intermediate for amino acid derivatization and phosphonate-containing scaffold construction.
1. Peptide Synthesis
Dimethyl ((3S)-4,4-dimethyl-3-(Boc-amino)-2-oxopentyl)phosphonate supports peptide building workflows by combining a Boc-protected amine with a backbone carbonyl that can participate in standard peptide coupling after Boc removal. The (3S) configuration fixes stereochemical identity at the amino acid center, while the phosphonate ester can be carried through coupling steps as a stable, non-interfering group under many peptide synthesis conditions. Carbamate protection enables selective deprotection to reveal the nucleophilic amine for sequential N-terminal elongation, and the phosphonate moiety can be positioned to yield phosphonate-containing peptide analogs. Downstream, deprotection or phosphonate functional-group conversion can furnish phosphorylated mimics used for studying backbone recognition and peptide stability trends in synthetic and biochemical research.
2. Phosphorylation Mimetic Design
Dimethyl ((3S)-4,4-dimethyl-3-(Boc-amino)-2-oxopentyl)phosphonate is suitable for chemical biology and molecular design efforts targeting phosphorylation-mimetic motifs, where the phosphonate group models a negatively charged phosphate at physiological pH. The amino acid-derived stereocenter and carbonyl pattern help align the phosphonate relative to the peptide backbone, enabling incorporation into peptide fragments, peptidomimetics, or constrained analogs. Boc protection provides orthogonal control over amine reactivity during scaffold assembly, allowing the phosphonate to remain in a protected ester state until the desired stage of functionalization. The resulting phosphonate-bearing derivatives can be used as tools for probing kinase-like recognition elements, binding-site electrostatics, and structure-dependent molecular interactions without requiring a free phosphate during early synthetic steps.
3. Protected Amino Acid Intermediate
Dimethyl ((3S)-4,4-dimethyl-3-(Boc-amino)-2-oxopentyl)phosphonate functions as a chiral, protected amino acid intermediate for fine chemical synthesis routes that require a Boc-protected nitrogen and a masked phosphate equivalent. The dimethyl phosphonate ester provides a chemically manageable handle for stepwise synthesis, while the Boc group enables controlled conversion to an activated coupling partner or further derivatization at the amine. The presence of both a backbone carbonyl and a phosphonate-bearing side chain supports downstream transformations into C-terminal modified amino acid derivatives, peptide building blocks, or phosphonate-functional fragments for library synthesis. Industrially relevant process chemistry can employ the stable protected groups to design scalable sequences where orthogonal deprotection and late-stage phosphonate conversion are needed to control impurity profiles and intermediate handling.
4. Bioconjugation Chemistry
Dimethyl ((3S)-4,4-dimethyl-3-(Boc-amino)-2-oxopentyl)phosphonate can be applied in bioconjugation and biomolecule modification strategies that leverage phosphonate electronegativity and amino acid-derived stereochemistry for controlled coupling. The Boc-protected amine can be converted to a reactive handle for attachment to linkers, surfaces, or carrier molecules after orthogonal deprotection, while the phosphonate ester can remain protected during conjugation to reduce side reactions. The chiral center and carbonyl framework can help maintain defined spatial presentation of the phosphonate group in conjugated constructs, supporting reproducible binding or recognition behavior in chemical biology studies. Downstream, phosphonate ester conversion can yield more reactive phosphate-like functionalities for subsequent conjugation steps, enabling construction of phosphonate-decorated probes, affinity reagents, or analytical standards.
5. Analytical Research Standards
Dimethyl ((3S)-4,4-dimethyl-3-(Boc-amino)-2-oxopentyl)phosphonate is useful for analytical method development and reference material preparation in studies involving phosphonate-containing amino acid derivatives and peptide analogs. The combination of a protected amino acid scaffold and a dimethyl phosphonate provides a defined, traceable chemical structure that can serve as an internal calibration or structural benchmark for LC-MS/MS fragmentation behavior and phosphonate stability assessments. Boc protection and the (3S) stereocenter support consistent chromatographic and mass spectrometric signatures across synthetic batches, aiding method transfer and impurity tracking during derivatization workflows. The compound's defined functional groups also enable generation of related standards through controlled deprotection or phosphonate conversion, supporting robust characterization of downstream peptide building blocks and phosphonate-modified products.
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