DL-Isovaline is a free, non-proteinogenic amino acid derivative of isovaleric acid featuring a branched aliphatic side chain (isopropyl-like) attached to the alpha carbon, placing it within the class of aliphatic amino acids. It contains both a primary amino group and a carboxyl functional group, and the "DL" designation indicates a racemic mixture of stereoisomers at the alpha stereocenter. DL-Isovaline is used in peptide and amino acid chemistry workflows where racemic amino acids are required for structure-activity studies, synthetic method development, or analytical method calibration involving defined amino acid standards.
CAT No: CP07601
DL-Isovaline is a branched-chain amino acid (α-aminoisovaleric acid) with an isopropyl side chain, existing as a racemic mixture (DL) at the α-carbon where the stereocenter is defined. The molecule contains a primary amino group and a carboxylic acid, enabling salt formation and standard amino-acid coupling chemistry after appropriate activation. Side-chain steric bulk and hydrophobic character influence conformational preferences in peptides and can affect chromatographic behavior during analytical method development. As an amino acid building block and chiral precursor precursor stream, DL-Isovaline is commonly handled through derivatization, protection/deprotection, and resolution strategies to access either enantiomer or to prepare downstream functionalized intermediates.
1. Peptide Building Block
DL-Isovaline is applied in peptide synthesis and peptide analog construction where an isopropyl-bearing side chain is required to tune hydrophobicity and steric profile. The amino and carboxyl functionalities participate in standard peptide coupling after conversion to an N-protected amino acid derivative and activation of the carboxyl group, supporting C-terminal incorporation into linear sequences. Racemic composition can be used for non-stereospecific studies, library synthesis, or for generating diastereomeric mixtures that are later resolved at the peptide or intermediate stage. Downstream, DL-Isovaline-derived residues can be used to prepare amide-linked fragments for structure-activity relationship studies and to support method development for peptide purification and characterization.
2. Chiral Resolution Intermediate
DL-Isovaline is suitable as a chiral synthetic intermediate in workflows that separate enantiomers or generate enantiopure derivatives for stereochemically defined studies. The α-stereocenter enables conversion into diastereomeric salts or derivatives using stereoselective resolving agents, followed by crystallization or chromatographic separation. The free amino acid functionality supports formation of protected intermediates that preserve stereochemical information through subsequent transformations such as esterification, N-protection, and side-chain functionalization. Resulting enantiopure isovaline building blocks can then feed into protected amino acid synthesis and stereodefined peptide construction, including incorporation into unnatural amino acid sequences.
3. Amino Acid Derivatization Chemistry
DL-Isovaline is utilized in amino acid derivatization and analytical chemistry where controlled functional group transformation is needed for detection, quantification, or downstream synthesis. The carboxylic acid can be converted to esters or activated derivatives to enable coupling chemistry, while the primary amine can be protected (e.g., carbamate or amide protection) to manage chemoselectivity during multistep routes. Branched-chain structure can influence derivatization kinetics and chromatographic retention, making DL-Isovaline a practical substrate for optimizing derivatization conditions and validating analytical methods for amino acid profiling. Functionalized derivatives prepared from DL-Isovaline can also serve as intermediates for further conversion into peptidomimetic scaffolds or hydrophobic side-chain analogs.
4. Process Chemistry Intermediate
DL-Isovaline is employed in process chemistry and fine chemical synthesis as a readily available amino acid feedstock for producing protected amino acid intermediates and downstream specialty chemicals. The presence of both amino and acid groups supports scalable conversion into N-protected forms and activated carboxyl derivatives that integrate into peptide coupling or fragment assembly on manufacturing-relevant timelines. Racemic material can reduce supply constraints when stereochemical purity is not required at the intermediate stage, with later resolution or stereoselective steps applied only when enantiopurity becomes necessary. Downstream utility includes preparation of amino acid esters, protected derivatives for automated synthesis platforms, and intermediate streams used to manufacture amino-acid-based building blocks for research and industrial supply chains.
5. Chemical Biology And SAR Screening
DL-Isovaline is applied in chemical biology research and structure-activity relationship studies where incorporation of a hydrophobic, branched residue can modulate binding-site interactions without requiring a specific enantiomer. The isopropyl side chain contributes steric and hydrophobic effects that can be systematically varied across peptide or peptidomimetic libraries to probe sequence-dependent recognition. N- and C-terminal modification strategies compatible with peptide chemistry can be used to generate fragments for conjugation handles, stability tuning, or assay-compatible constructs. Resulting DL-Isovaline-containing analogs can support comparative SAR workflows, fragment-based optimization, and analytical evaluation of structure-dependent behavior in amino-acid-derived molecular series.
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