N-α-(t-Butoxycarbonyl)-β-(t-butyl)-DL-alanine
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N-α-(t-Butoxycarbonyl)-β-(t-butyl)-DL-alanine

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Category
BOC-Amino Acids
Catalog number
BAT-003186
CAS number
507264-54-2
Molecular Formula
C12H23NO4
Molecular Weight
245.31
N-α-(t-Butoxycarbonyl)-β-(t-butyl)-DL-alanine
IUPAC Name
4,4-dimethyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid
Synonyms
Boc-DL-Ala(tBu)-OH; Boc-DL-Leu(Me)-OH; N-α-(t-Butoxycarbonyl)-γ-methyl-DL-leucine; 4,4-dimethyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid; N-BOC-3-T-BUTYL-DL-ALANINE; 2-(tert-butoxycarbonylamino)-4,4-dimethylpentanoic acid
Purity
≥ 95%
Density
1.048±0.060 g/cm3
Boiling Point
364.4±25.0 °C
InChI
InChI=1S/C12H23NO4/c1-11(2,3)7-8(9(14)15)13-10(16)17-12(4,5)6/h8H,7H2,1-6H3,(H,13,16)(H,14,15)
InChI Key
PUQVQDMFCAGQQB-UHFFFAOYSA-N
Canonical SMILES
CC(C)(C)CC(C(=O)O)NC(=O)OC(C)(C)C

N-α-(t-Butoxycarbonyl)-β-(t-butyl)-DL-alanine, a synthetic amino acid derivative, finds diverse applications in peptide synthesis and other biochemical endeavors. Here are the key applications presented with high perplexity and burstiness:

Peptide Synthesis: Serving as a fundamental constituent in solid-phase peptide synthesis, N-α-(t-Butoxycarbonyl)-β-(t-butyl)-DL-alanine acts as a crucial building block. Its shielded amino and carboxyl groups play a pivotal role in preventing undesirable side reactions during the synthesis process, facilitating the efficient generation of intricate peptides with unparalleled purity and precision.

Pharmaceutical Development: In the realm of pharmaceutical research, this compound assumes a pivotal role in the creation of peptide-based drugs characterized by enhanced stability and bioavailability. The presence of the t-butyl group offers steric protection, thereby mitigating peptide degradation by proteolytic enzymes. This attribute proves especially valuable in formulating therapeutics necessitating an extended half-life in the circulatory system.

Protein Engineering: Researchers leverage N-α-(t-Butoxycarbonyl)-β-(t-butyl)-DL-alanine to introduce non-natural amino acids into proteins, thereby reshaping their properties and functionalities. This innovative approach empowers the development of proteins endowed with superior or novel attributes, such as heightened binding affinities or modified catalytic capabilities. These tailored proteins find applications across a spectrum of industrial and therapeutic domains.

Biochemical Studies: Esteemed for its role in elucidating protein structure and function, this compound facilitates in-depth investigations into protein behavior. By incorporating it into peptide sequences, scientists can effect specific alterations that facilitate the exploration of protein folding dynamics, stability, and interactions. These studies yield invaluable insights into the fundamentals of protein design and operation, propelling the advancement of biomolecular tools and therapeutic interventions.

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