Fmoc-DL-3-Aminoisobutyric acid is an Fmoc-protected amino acid derivative featuring the 3-aminioisobutyric acid side chain and a backbone bearing both an amino functionality and a carboxyl group masked for peptide coupling. The molecule is presented as a DL mixture, and the amino terminus is protected by the fluorenylmethoxycarbonyl (Fmoc) group, while the side chain contains a primary amine that can be used for further derivatization or for orthogonal protection strategies in peptide chemistry. In synthesis workflows, it functions as a protected building block for solid-phase or solution-phase incorporation of 3-aminioisobutyric acid-containing residues into peptides and peptide-related intermediates, and the free side-chain amine supports downstream conjugation, labeling, or structure-activity study modifications.
CAT No: CP04005
CAS No:186320-19-4
Synonyms/Alias:186320-19-4;3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpropanoicacid;3-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-2-methylpropanoicacid;3-({[(9H-FLUOREN-9-YL)METHOXY]CARBONYL}AMINO)-2-METHYLPROPANOICACID;ACMC-20a7ht;ACMC-20a7hu;AC1MU9KD;SCHEMBL60494;SCHEMBL15727228;CTK8B8542;fmoc-dl-beta-aminoisobutyricacid;Fmoc-DL-3-Aminoisobutyricacid;MolPort-006-705-649;9731AA;ANW-60641;AKOS012614302;RTR-061910;AK-87762;AM005717;AM018790;PL016974;KB-232302;TR-061910;I14-39969;3-(9H-fluoren-9-ylmethoxycarbonylamino)-2-methylpropanoicacid
Fmoc-DL-3-Aminoisobutyric acid is an Fmoc-protected amino acid derivative featuring a 3-aminoisobutyric acid side chain that contains an additional stereogenic center relative to the parent carbon skeleton, presented here as a DL (racemic) mixture. The molecule contains an Fmoc carbamate on the α-amino group and an unprotected carboxylic acid, enabling standard peptide coupling after carboxyl activation while maintaining orthogonality to the Fmoc deprotection step. The amino acid's branched side chain provides steric and conformational features that can influence local peptide geometry and side-chain packing in peptide analogs. The combination of a protected amine and a reactive acid makes it a practical chiral amino acid intermediate for protected amino acid synthesis workflows and downstream derivatization strategies.
1. Peptide Synthesis
Fmoc-DL-3-Aminoisobutyric acid is used in peptide building workflows where Fmoc-based solid-phase peptide synthesis or solution-phase coupling requires a stable N-protected amino acid. The Fmoc carbamate protects the α-amino functionality during chain assembly, while the free carboxylic acid participates in amide bond formation after activation, supporting incorporation at defined positions within peptide sequences. The branched 3-aminoisobutyric acid side chain can introduce steric bias and altered conformational preferences, which can be exploited in peptide libraries and sequence optimization studies. The racemic DL stereochemistry enables access to both enantiomeric incorporation patterns for structure-activity relationship studies and comparative peptide analog construction.
2. Amino Acid Derivatization
Fmoc-DL-3-Aminoisobutyric acid is applicable to amino acid derivatization routes that leverage the orthogonality of Fmoc protection to carboxyl functional group transformations. The free carboxylic acid can be converted into activated esters, amides, or other downstream intermediates, while the Fmoc group can be retained during selective side-chain or carboxyl modifications to control chemoselectivity. The branched side chain bearing an additional amino substituent can participate in further protection strategies or subsequent functional group installation, supporting generation of N-functionalized amino acid derivatives. The resulting products can serve as biochemical research intermediates for constructing modified peptide building blocks and for mapping how side-chain substitution patterns affect molecular recognition.
3. Peptidomimetics And SAR Studies
Fmoc-DL-3-Aminoisobutyric acid is suitable for peptidomimetic construction and structure-activity relationship studies where amino acid sterics and stereochemical composition influence binding-site interactions. The 3-aminoisobutyric acid motif contributes a compact, branched side chain that can modulate hydrophobic contacts and local backbone/side-chain orientation in peptide analogs. The Fmoc-protected α-amino group supports sequential assembly into defined scaffolds, enabling systematic variation of residue identity and stereochemical content across analog series. The DL format can be employed to generate racemic peptide analogs for comparative SAR mapping, supporting downstream selection of more stereochemically defined variants when needed.
4. Pharmaceutical Intermediate Preparation
Fmoc-DL-3-Aminoisobutyric acid is used as a protected amino acid intermediate in fine chemical synthesis routes that require controlled N-protection during multi-step manufacturing of peptide-related intermediates. The Fmoc carbamate provides a robust handle for protecting-group management, allowing manufacturing sequences to proceed through carboxyl activation and coupling steps without premature amine reactivity. The free carboxylic acid enables conversion into coupling-ready forms for incorporation into larger fragments, supporting the preparation of peptide building blocks used in active pharmaceutical ingredient (API) precursor synthesis. The branched amino acid structure can be carried through as a defined stereochemical element in intermediate sets, supporting consistent downstream assembly and analytical verification of peptide fragment composition.
5. Chemical Biology And Protein Engineering
Fmoc-DL-3-Aminoisobutyric acid is applicable to chemical biology workflows and protein engineering efforts that require incorporation of amino acid residues into peptide tags, linker regions, or engineered binding domains. The Fmoc-protected α-amino group enables reproducible peptide incorporation, while the branched 3-aminoisobutyric acid side chain can affect solubility, steric accessibility, and local conformational behavior of engineered constructs. The racemic stereochemistry can be used in exploratory labeling or scaffold-generation studies where multiple stereochemical outcomes are acceptable for screening and subsequent refinement. The resulting peptide or peptide-derived constructs can be employed as biochemical research intermediates for studying structure-function relationships at the molecular level, including how side-chain geometry impacts recognition and assembly.
6. Analytical Research Standards
Fmoc-DL-3-Aminoisobutyric acid is suitable for analytical research and method development where defined amino acid derivatives serve as reference materials for LC-MS, HPLC, or peptide mapping workflows. The presence of an Fmoc-protected amino group supports consistent detection behavior and facilitates derivatization-compatible handling during analytical sample preparation. The free carboxylic acid and branched side chain provide characteristic fragmentation patterns after activation or coupling, aiding identification of the residue in peptide fragments. The DL stereochemical mixture supports comparative quantitation and method robustness when analyzing racemic peptide libraries or stereochemically mixed intermediate sets in applied peptide chemistry.
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