Boc-alpha-Me-DL-Val-OH is a protected, non-natural amino acid derivative based on the valine scaffold bearing an alpha-methyl substituent (α-Me) and a Boc-protected amino group, with the DL designation indicating a racemic mixture at the stereogenic center. The molecule contains a Boc carbamate on the amino functionality and a free carboxylic acid, while the side chain retains the isopropyl group characteristic of valine and the additional alpha-methyl substitution changes steric and conformational preferences during coupling. As a stepwise peptide-synthesis intermediate, this protected amino acid is used to introduce the α-methylated valine residue into peptide chains under conditions that maintain the Boc group until deprotection and subsequent amide bond formation.
CAT No: CP26362
CAS No:139938-00-4
Synonyms/Alias:BOC-ALPHA-ME-DL-VAL-OH;139938-00-4;Boc-alpha-methyl-DL-Val-OH;SCHEMBL3528810;CTK8F0023;6264AH;AKOS013464347;RTC-066293;AM004870;KB-90578;TC-066293;I14-32634;2-[(TERT-BUTOXYCARBONYL)AMINO]-2,3-DIMETHYLBUTANOICACID
Boc-alpha-Me-DL-Val-OH is a Boc-protected, alpha-methylated valine derivative supplied as a DL stereochemical mixture, featuring a tert-butoxycarbonyl (Boc) group on the amino terminus and a free carboxylic acid for downstream coupling. The alpha-methyl substitution on the backbone introduces steric and conformational bias relative to unmodified valine, making this building block valuable in peptide and peptidomimetic synthesis where backbone substitution is used to tune structure and chemical behavior. As a protected amino acid intermediate, it is typically handled as a reagent for stepwise assembly of modified peptide segments or as a chiral-agnostic precursor for SAR-focused library work.
1. Backbone-Modified Peptide Synthesis
Boc-alpha-Me-DL-Val-OH is used by peptide synthesis groups to introduce an alpha-methylated valine residue into peptides and peptidomimetics, enabling systematic structure-property studies in custom peptide manufacturing and academic medicinal chemistry. The Boc-protected amino terminus supports controlled segment coupling in solution-phase workflows, while the free carboxylic acid provides the necessary functionality for forming the next amide bond during assembly. Researchers commonly select this derivative when they want to compare unmodified valine versus alpha-methylated analogs to assess how backbone substitution affects conformational preferences, synthetic robustness, and downstream reactivity of the peptide scaffold.
2. Peptidomimetic SAR Building Block
Boc-alpha-Me-DL-Val-OH serves as a practical amino acid building block for peptidomimetic development and SAR (structure-activity relationship) campaigns, especially when a backbone-substituted residue is required to probe steric and conformational effects. Medicinal chemistry teams often incorporate alpha-methylated amino acid units to create analog series that differ at a single, well-defined position, supporting parallel synthesis of peptide-like candidates for biochemical screening and chemical biology tool development. The DL form is frequently chosen in early-stage library construction when the goal is to generate material efficiently for comparative studies, with stereochemical resolution or downstream separation addressed later if needed.
3. Protected Amino Acid Intermediate Supply
Boc-alpha-Me-DL-Val-OH is supplied as a protected amino acid intermediate for downstream chemical manufacturing steps where controlled protection of the amino functionality is required prior to coupling chemistry. Pharmaceutical intermediate development teams and specialty synthesis providers use this reagent to prepare modified amino acid segments for custom peptide synthesis, including workflows that demand stable handling of the N-protected group and a carboxylic acid handle for activation and condensation. The defined Boc protection pattern helps streamline reagent logistics in multi-step assembly, particularly when building blocks are stored and batched for later coupling into larger peptide constructs.
4. Stereochemical-Agnostic Library Preparation
Boc-alpha-Me-DL-Val-OH is frequently selected for stereochemical-agnostic library preparation in research settings where rapid generation of analogs is prioritized over immediate stereochemical purity. Because the material is provided as a DL mixture, it supports efficient construction of peptide and peptidomimetic libraries that incorporate alpha-methylated valine-like residues without requiring separate enantiomer-specific procurement at the earliest stage. This approach is commonly used by chemical biology and medicinal chemistry groups to map position-specific effects within a scaffold, after which downstream purification, stereochemical characterization, or selective re-synthesis can be performed for the most informative analogs.
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