Boc-β-iodo-Ala-OtBu
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Boc-β-iodo-Ala-OtBu

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Category
BOC-Amino Acids
Catalog number
BAT-010881
CAS number
1057341-65-7
Molecular Formula
C12H22INO4
Molecular Weight
371.21
IUPAC Name
tert-butyl (2R)-3-iodo-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
Synonyms
(R)-2-tert-butoxycarbonylamino-3-iodopropionic acid tert-butyl ester; N-(tert-Butoxycarbonyl)-3-iodo-L-alanine tert-butyl ester; Boc β iodo Ala OtBu
InChI
InChI=1S/C12H22INO4/c1-11(2,3)17-9(15)8(7-13)14-10(16)18-12(4,5)6/h8H,7H2,1-6H3,(H,14,16)/t8-/m0/s1
InChI Key
ZHILIIPKDAXSDM-QMMMGPOBSA-N
Canonical SMILES
CC(C)(C)OC(=O)C(CI)NC(=O)OC(C)(C)C

Boc-β-iodo-Ala-OtBu, a versatile chemical compound utilized in peptide synthesis and various organic synthesis processes, has diverse applications across multiple domains. Here are the key applications presented with a high degree of perplexity and burstiness:

Peptide Synthesis: Serving as a fundamental building block in peptide synthesis, Boc-β-iodo-Ala-OtBu plays a crucial role in crafting peptide chains. Its iodine substituent enables selective reactions facilitating the incorporation of diverse functionalities into peptide structures. This capability not only advances the development of therapeutic peptides but also enhances their utility in biochemical research, showcasing the compound's versatility and importance in the field.

Chemical Probes: Utilizing Boc-β-iodo-Ala-OtBu in the generation of chemical probes for exploring biological systems is a sophisticated application of this compound. The iodine atom within it enables efficient radiolabeling, a valuable feature for imaging studies and tracking biochemical pathways. These probes are indispensable tools for unraveling intricate molecular interactions and pinpointing specific biomolecules, shedding light on the complex dynamics within biological systems with precision and sophistication.

Click Chemistry: The inclusion of the iodo group in Boc-β-iodo-Ala-OtBu renders it a valuable reagent in click chemistry, a modular approach to chemical synthesis. Capable of engaging in reactions like the Sonogashira coupling, this compound contributes to the creation of intricate molecules with exceptional precision. This application holds significant implications for the development of novel pharmaceuticals and advancements in materials science research, showcasing the compound's potential to foster innovation and discovery in diverse scientific disciplines.

Proteomics Research: In the realm of proteomics research, the incorporation of Boc-β-iodo-Ala-OtBu into polypeptides enables the study of post-translational modifications and protein-protein interactions with intricate detail. By engineering peptides with specific modifications, researchers can explore how these alterations impact protein functionality and stability, offering insights into disease mechanisms and potential drug targets. This application underscores the compound's role in elucidating the complexities of cellular processes and advancing our understanding of biological systems at a molecular level.

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