N-α-(t-Butoxycarbonyl)-3-(1-methylbenzimidazol-2-yl)-L-alanine
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N-α-(t-Butoxycarbonyl)-3-(1-methylbenzimidazol-2-yl)-L-alanine

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Category
BOC-Amino Acids
Catalog number
BAT-001379
CAS number
2389078-86-6
Molecular Formula
C16H21N3O4
Molecular Weight
319.36
IUPAC Name
3-(1-methylbenzimidazol-2-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
Synonyms
Boc-Ala[2-Bim(1-Me)]-OH; Boc-Ala(1-Methylbenzimidazol-2-yl)-OH
Purity
≥ 95%
Storage
Store at 2-8 °C
InChI
InChI=1S/C16H21N3O4/c1-16(2,3)23-15(22)18-11(14(20)21)9-13-17-10-7-5-6-8-12(10)19(13)4/h5-8,11H,9H2,1-4H3,(H,18,22)(H,20,21)
InChI Key
GHJTVSGOZPWXOR-UHFFFAOYSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CC1=NC2=CC=CC=C2N1C)C(=O)O

N-α-(t-Butoxycarbonyl)-3-(1-methylbenzimidazol-2-yl)-L-alanine, a specialized chemical reagent utilized in peptide synthesis and various biochemical applications, boasts a diverse range of functionalities. Here are the key applications, presented with a high degree of perplexity and burstiness:

Peptide Synthesis: Serving as a cornerstone in solid-phase peptide synthesis, this compound acts as a protected amino acid derivative, utilizing its t-Butoxycarbonyl (Boc) group to maintain the amino group inert during coupling reactions. This meticulous protection plays a pivotal role in the incremental assembly of peptides, ensuring unparalleled purity and yield in the final products.

Protein Engineering: Within the realm of protein engineering, this reagent emerges as a powerful tool for implementing targeted modifications in peptides and proteins. By integrating this altered amino acid, researchers can tailor protein characteristics, such as stability and binding affinity, to desired specifications. This transformative application is instrumental in crafting proteins for therapeutic and industrial applications, pushing the boundaries of biological innovation.

Drug Design: Playing a critical role in developing peptide-based pharmaceutical candidates, N-α-(t-Butoxycarbonyl)-3-(1-methylbenzimidazol-2-yl)-L-alanine possesses a unique structure that enhances the stability of peptide drugs, rendering them more resilient to enzymatic breakdown. This enhanced stability is essential for achieving sustained therapeutic effects, revolutionizing the landscape of drug design and delivery.

Biophysical Studies: Enabling in-depth exploration of protein-peptide interactions and conformational dynamics, this compound finds use in biophysical studies to unravel molecular mechanisms. Its integration into peptides facilitates precise investigations using advanced techniques like Nuclear Magnetic Resonance (NMR) spectroscopy and X-ray crystallography. These studies offer profound insights into the structural underpinnings of protein functionality and interplay, advancing our comprehension of complex biological systems.

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