N-α-(t-Butoxycarbonyl)-3-(benzimidazol-2-yl)-L-alanine
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N-α-(t-Butoxycarbonyl)-3-(benzimidazol-2-yl)-L-alanine

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Category
BOC-Amino Acids
Catalog number
BAT-001380
CAS number
2389078-30-0
Molecular Formula
C15H19N3O4
Molecular Weight
305.33
IUPAC Name
3-(1H-benzimidazol-2-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
Synonyms
Boc-Ala(2-Bim)-OH; Boc-Ala(Benzimidazol-2-yl)-OH
Storage
Store at 2-8 °C
InChI
InChI=1S/C15H19N3O4/c1-15(2,3)22-14(21)18-11(13(19)20)8-12-16-9-6-4-5-7-10(9)17-12/h4-7,11H,8H2,1-3H3,(H,16,17)(H,18,21)(H,19,20)
InChI Key
VKYOVEGLCCXLBT-UHFFFAOYSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CC1=NC2=CC=CC=C2N1)C(=O)O

N-α-(t-Butoxycarbonyl)-3-(benzimidazol-2-yl)-L-alanine, a chemical compound commonly utilized in medicinal and biochemical research, boasts a myriad of versatile applications. Here are the key applications intricately presented with high perplexity and burstiness:

Peptide Synthesis: Playing a pivotal role in solid-phase peptide synthesis, this compound acts as a shielded amino acid, with the t-Butoxycarbonyl (Boc) group serving as a guardian for the amino terminus, thwarting undesired side reactions. Upon completion of peptide synthesis, the Boc group can be meticulously stripped away under acidic conditions, unveiling the liberated amine with precision.

Drug Discovery: Within the realm of drug discovery, N-α-(t-Butoxycarbonyl)-3-(benzimidazol-2-yl)-L-alanine shines as a foundational unit for crafting peptide-based drugs or drug candidates. Infused with the pharmacologically potent benzimidazole moiety, it harbors potential as an enzyme inhibitor, captivating researchers in their quest to engineer novel molecules endowed with tailored biological functions.

Bioconjugation Studies: In the intricate domain of bioconjugation, this compound emerges as a valuable asset, capable of forming conjugates with augmented properties when tethered to other molecules. Its adaptability allows for the fusion with proteins or other macromolecules, fostering the creation of diagnostic tools or therapeutic agents through meticulous modification steps facilitated by the Boc-protected alanine derivative.

Enzyme Studies: Positioned at the forefront of enzyme studies, N-α-(t-Butoxycarbonyl)-3-(benzimidazol-2-yl)-L-alanine proves indispensable for scrutinizing enzyme-substrate interactions and unraveling the intricacies of enzyme kinetics. The benzimidazole entity engages with enzyme active sites, unveiling insights into enzyme mechanisms that are invaluable for designing potent enzyme inhibitors and unraveling the mysteries of catalytic processes.

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