Fmoc-beta-Iodo-L-Ala-Obzl
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Fmoc-beta-Iodo-L-Ala-Obzl

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Category
Fmoc-Amino Acids
Catalog number
BAT-008708
CAS number
869107-32-4
Molecular Formula
C25H22INO4
Molecular Weight
527.35
IUPAC Name
benzyl 2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-iodopropanoate
Synonyms
Fmoc beta Iodo L Ala Obzl
Purity
95%
InChI
InChI=1S/C25H22INO4/c26-14-23(24(28)30-15-17-8-2-1-3-9-17)27-25(29)31-16-22-20-12-6-4-10-18(20)19-11-5-7-13-21(19)22/h1-13,22-23H,14-16H2,(H,27,29)
InChI Key
OXWWBZLBMCZQLM-UHFFFAOYSA-N
Canonical SMILES
C1=CC=C(C=C1)COC(=O)C(CI)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24

Fmoc-beta-Iodo-L-Ala-Obzl, a specialized amino acid derivative, plays a crucial role in peptide synthesis and biochemical research. Here are the key applications of Fmoc-beta-Iodo-L-Ala-Obzl, presented with high perplexity and burstiness:

One of the primary applications of Fmoc-beta-Iodo-L-Ala-Obzl is in the synthesis of peptides and peptidomimetics. This compound is particularly valuable due to its protected amino and carboxyl groups, which allow for selective deprotection and sequential elongation of peptide chains. The iodine atom at the beta position provides a reactive site that can be exploited for further functionalization through various coupling reactions, such as Suzuki, Heck, or Sonogashira coupling. This makes it an essential building block for researchers developing novel peptides with specific functional properties or for those aiming to modify existing peptide structures for enhanced biological activity.

Another key application is in the field of medicinal chemistry, where Fmoc-beta-Iodo-L-Ala-Obzl serves as a precursor for the synthesis of bioactive compounds. The incorporation of the beta-iodo-alanine derivative into peptide sequences can lead to the formation of unique bioactive motifs that interact with biological targets in specific ways. This compound is especially useful in the design of enzyme inhibitors, receptor agonists or antagonists, and other therapeutic agents. By introducing functionalities at the beta position, chemists can create a variety of derivatives that may exhibit improved pharmacokinetic and pharmacodynamic properties, thus advancing drug discovery projects.

In the realm of material science and nanotechnology, Fmoc-beta-Iodo-L-Ala-Obzl plays a crucial role in the fabrication of peptide-based materials. These materials can self-assemble into nanostructures such as nanofibers, nanotubes, or hydrogels, which have promising applications in drug delivery, tissue engineering, and biosensing. The beta-iodo substitution allows for the precise placement of additional functional groups, which can modulate the self-assembly behavior and mechanical properties of the resulting materials. Researchers can thus design peptide-based materials with tailored functionalities for specific applications, harnessing the unique properties of this compound.

Lastly, Fmoc-beta-Iodo-L-Ala-Obzl is used in the study of protein-protein interactions and molecular recognition processes. Structural modifications introduced by the beta-iodo substituent can serve as probes to investigate the binding mechanisms and the spatial arrangement of amino acid residues within protein complexes. This can provide valuable insights into the dynamics of protein folding, conformational changes, and interaction networks. Moreover, labeled peptides containing Fmoc-beta-Iodo-L-Ala-Obzl can be employed in techniques such as X-ray crystallography or NMR spectroscopy to elucidate the three-dimensional structures of protein complexes, contributing significantly to structural biology research.

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