Description
(R)-2-((tert-Butoxycarbonyl)amino)-2-methylbutanoic acid (CAS: 123254-58-0) is a high-purity chiral amino acid derivative widely used in peptide synthesis and pharmaceutical research. This Boc-protected D-isovaline analog features a tert-butoxycarbonyl (Boc) group, ensuring optimal stability during solid-phase peptide synthesis (SPPS) and other organic transformations. With a molecular formula of C10H19NO4, it serves as a critical building block for designing bioactive peptides, peptidomimetics, and asymmetric catalysts. The compound is rigorously characterized by HPLC, NMR, and MS to guarantee ≥95% purity, making it ideal for sensitive applications in medicinal chemistry and structural biology. Store desiccated at -20°C to maintain reactivity.
Properties
- CAS Number: 123254-58-0
- Complexity: 257
- IUPAC Name: (2R)-2-(tert-butoxycarbonylamino)-2-methyl-butanoic acid
- InChI: InChI=1S/C10H19NO4/c1-6-10(5,7(12)13)11-8(14)15-9(2,3)4/h6H2,1-5H3,(H,11,14)(H,12,13)/t10-/m1/s1
- InChI Key: SHZXLTCEPXVCSV-SNVBAGLBSA-N
- Exact Mass: 217.13140809
- Molecular Formula: C10H19NO4
- Molecular Weight: 217.26
- SMILES: CC[C@](C)(C(=O)O)NC(=O)OC(C)(C)C
- Topological: 75.6
- Monoisotopic Mass: 217.13140809
- Synonyms: 123254-58-0, (R)-2-((tert-Butoxycarbonyl)amino)-2-methylbutanoic acid, Boc-D-isovaline, D-Isovaline, N-[(1,1-dimethylethoxy)carbonyl]-, (2R)-2-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid, Boc-a-Me-D-Gly(Ethyl)-OH, Boc-iso-Valine, MFCD12963786, N-BOC-D-ISOVALINE, (R)-N-Boc-a-ethylalanine, (S)-N-Boc-a-ethylalanine, SCHEMBL1979477, (R)-2-((tert-Butoxycarbonyl)amino)-2-methylbutanoicacid, (R)-2-(tert-butoxycarbonylamino)-2-methylbutanoic acid, (2R)-2-(tert-butoxycarbonylamino)-2-methyl-butanoic acid, SHZXLTCEPXVCSV-SNVBAGLBSA-N, Boc-D-Isovaline (Boc-D-Iva-OH), AKOS025117414, DS-8339, CS-0039041, F15253, (2R)-2-{[(tert-butoxy)carbonyl]amino}-2-methylbutanoic acid
This compound is primarily employed as a chiral auxiliary in asymmetric synthesis and as a precursor for non-natural amino acid incorporation into peptides. It is essential for studying enzyme-substrate interactions due to its sterically hindered α-methyl group. Researchers also utilize it to modulate peptide conformation and stability in drug discovery projects targeting GPCRs and proteases.
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