Fmoc-4-(neopentyloxysulfonyl)-Abu-OH is an Fmoc-protected amino acid derivative in which the side chain corresponds to 4-substituted Abu (aminobutyric acid) bearing a neopentyloxysulfonyl substituent. The molecule contains an Fmoc carbamate on the amino functionality and a free carboxylic acid, while the side-chain sulfonyl group is masked as a neopentyloxysulfonyl ester-like substituent that provides a bulky, polar handle for controlled reactivity during peptide assembly. In peptide synthesis workflows, the Fmoc protection supports stepwise coupling at the α-amino position, and the sulfonyl-based substituent can be used to introduce a chemically differentiated side chain for structure-activity studies, chemical biology labeling strategies, or preparation of further amino acid and peptide derivatives.
CAT No: CP26814
CAS No:220951-81-5
Synonyms/Alias:Fmoc-4-(neopentyloxysulfonyl)-ABU-OH;220951-81-5;Fmoc-4-(neopentyloxysulfonyl)-L-aminobutyricacid;CTK8E9966;ZINC2573515;RT-012885
Fmoc-4-(neopentyloxysulfonyl)-Abu-OH is an Fmoc-protected, chiral amino acid derivative based on 4-aminobutyric acid (Abu) bearing a sulfonyl substituent at the 4-position and a neopentyloxysulfonyl (neopentyl oxy-sulfonyl) group that provides an additional, strongly electron-withdrawing handle. The molecule contains the Fmoc carbamate on the α-amino functionality, a free carboxylic acid for coupling chemistry, and a side-chain sulfonate/sulfonyl oxygen functionality that can participate in polarity-driven interactions and controlled reactivity during synthetic sequences. The chiral center in the Abu backbone supports stereodefined peptide construction, while the sulfonyl oxy substituent can influence solubility and compatibility with common peptide coupling and deprotection conditions. The combination of a protected amine, a reactive acid, and a functionalized side chain makes the compound a practical intermediate for peptide building block preparation and downstream functional group conversion in amino acid and peptide chemistry.
1. Peptide Synthesis
Fmoc-4-(neopentyloxysulfonyl)-Abu-OH is applied as an Fmoc-based peptide building block in solid-phase peptide synthesis and related protected amino acid assembly workflows. The Fmoc-protected α-amino group enables standard base-mediated deprotection to expose the coupling-ready amine, while the free carboxylic acid supports amide bond formation with activated carboxyl partners. The 4-position sulfonyl substituent on the Abu side chain can be retained through chain elongation to preserve side-chain functionality for later derivatization, enabling controlled incorporation of a polar, sulfonyl-bearing motif into peptide backbones. The resulting peptide intermediates can be used to generate sulfonyl-functionalized analogs for biochemical research and synthetic methodology development within peptide science.
2. Side-Chain Functionalization
Fmoc-4-(neopentyloxysulfonyl)-Abu-OH serves as a side-chain functionalization precursor in synthetic organic chemistry where a sulfonyl oxy motif is required at a defined position relative to the amino acid backbone. The neopentyloxysulfonyl group provides a protected sulfonyl-oxygen environment that can modulate reactivity during peptide coupling, then can potentially be transformed after peptide assembly through selective deprotection or functional group interconversion strategies. The Abu scaffold positions the sulfonyl functionality at the δ-like side-chain distance characteristic of 4-aminobutyric acid derivatives, supporting structure-defined spatial presentation of polar or hydrogen-bonding features. Downstream use includes preparing sulfonyl-containing peptide fragments, peptidomimetic scaffolds, and functionalized amide-linked intermediates that retain stereochemical integrity from the chiral amino acid precursor.
3. Chemical Biology Probes
Fmoc-4-(neopentyloxysulfonyl)-Abu-OH can be employed in chemical biology research for constructing labeled or reactive peptide-like probes that incorporate a sulfonyl oxy functionality. The Fmoc-protected amine and carboxylic acid allow incorporation into peptide sequences that can be used as substrates, affinity handles, or scaffold units for molecular recognition studies. The side-chain sulfonyl oxygen can contribute to specific physicochemical properties such as altered polarity and potential interaction patterns, which may be leveraged when designing peptide analogs for studying binding events or enzyme recognition. The compound's protected-amino acid format also supports sequential assembly of multi-component probe structures, enabling downstream conjugation or derivatization of the sulfonyl-bearing side chain in applied biochemical investigations.
4. Peptidomimetics And SAR Studies
Fmoc-4-(neopentyloxysulfonyl)-Abu-OH is suitable for peptidomimetic construction and structure-activity relationship (SAR) studies where defined incorporation of a sulfonyl-functionalized Abu unit is needed. The chiral Abu backbone and Fmoc chemistry support stereodefined placement of the side-chain sulfonyl group, which can be critical when comparing analogs that differ only in side-chain electronics or hydrogen-bonding capacity. The protected amino acid format facilitates stepwise synthesis of analog libraries by enabling consistent coupling chemistry and controlled retention of the sulfonyl oxy group during scaffold assembly. The resulting peptidomimetic intermediates can be used to generate structure-defined series for SAR-oriented molecular design and comparative evaluation in applied medicinal chemistry workflows.
5. Pharmaceutical Manufacturing Intermediates
Fmoc-4-(neopentyloxysulfonyl)-Abu-OH can be used in pharmaceutical manufacturing and process chemistry contexts as a protected amino acid intermediate for producing sulfonyl-functionalized peptide ingredients or peptide-based intermediates. The Fmoc carbamate and free carboxylic acid provide a predictable protection/deprotection logic compatible with standard peptide coupling operations, supporting scalable route design for protected amino acid synthesis and subsequent chain assembly. The neopentyloxysulfonyl side chain can be selected to control side-chain reactivity during manufacturing steps, helping manage functional group stability until the desired stage of downstream transformation. The compound's defined stereochemistry and functional group pattern make it suitable for generating consistent, structurally characterized intermediates used in fine chemical production and applied peptide manufacturing pipelines.
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