Description

N-[(1,1-Dimethylethoxy)carbonyl]-3-iodo-L-alanine ethyl ester (CAS No. 455264-61-6) is a high-purity, synthetic amino acid derivative designed for advanced research and pharmaceutical applications. With the molecular formula C₁₀H₁₈INO₄, this compound features a tert-butoxycarbonyl (Boc) protecting group and an iodo-substituted alanine ethyl ester moiety, making it a versatile intermediate in peptide synthesis and medicinal chemistry. Its IUPAC name, ethyl (2R)-3-iodo-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate, highlights its stereospecific (R)-configuration, ensuring precise reactivity in chiral synthesis. Ideal for use in cross-coupling reactions, radiolabeling, and proteomics research, this product is rigorously tested for purity (>98% by HPLC) and stability under controlled storage conditions (-20°C). Each batch is supplied with comprehensive analytical documentation, including ¹H NMR, ¹³C NMR, and mass spectrometry data.

Properties

• CAS Number: 455264-61-6
• Complexity: 250
• IUPAC Name: ethyl (2R)-2-(tert-butoxycarbonylamino)-3-iodo-propanoate
• InChI: InChI=1S/C10H18INO4/c1-5-15-8(13)7(6-11)12-9(14)16-10(2,3)4/h7H,5-6H2,1-4H3,(H,12,14)/t7-/m0/s1
• InChI Key: POBZRNDVBGJMTK-ZETCQYMHSA-N
• Exact Mass: 343.02806
• Molecular Formula: C10H18INO4
• Molecular Weight: 343.16
• SMILES: CCOC(=O)[C@H](CI)NC(=O)OC(C)(C)C
• Topological: 64.6
• Monoisotopic Mass: 343.02806
• Synonyms: 455264-61-6, N-[(1,1-Dimethylethoxy)carbonyl]-3-iodo-L-alanine ethyl ester, Ethyl (R)-2-((tert-butoxycarbonyl)amino)-3-iodopropanoate, n-boc-3-iodo-l-alanine ethyl ester, SCHEMBL5147608, MFCD12546208, DB-173033, G83923, (R)-ETHYL 2-((TERT-BUTOXYCARBONYL)AMINO)-3-IODOPROPANOATE, ethyl (2R)-3-iodo-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate

Application

This Boc-protected iodoalanine derivative is widely employed in peptide synthesis as a key building block for introducing iodine-labeled side chains, enabling downstream modifications like Suzuki-Miyaura couplings. It serves as a precursor for radiopharmaceuticals in PET imaging due to the iodine atom’s potential for isotopic substitution. Researchers also utilize it in solid-phase peptide synthesis (SPPS) to incorporate halogenated amino acids for structure-activity relationship (SAR) studies.

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