N-α-(t-Butoxycarbonyl)-β,β-dicyclohexyl-DL-alanine
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N-α-(t-Butoxycarbonyl)-β,β-dicyclohexyl-DL-alanine

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Category
BOC-Amino Acids
Catalog number
BAT-003187
CAS number
177795-78-7
Molecular Formula
C20H35NO4
Molecular Weight
353.50
N-α-(t-Butoxycarbonyl)-β,β-dicyclohexyl-DL-alanine
IUPAC Name
3,3-dicyclohexyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
Synonyms
Boc-DL-Ala(DCH)-OH; Boc-DL-Ala(Dicyclohexyl)-OH; Boc-(D,L)-Dch-OH; N-α-t-Butoxycarbonyl-β,β-dicyclohexyl-DL-alanine
InChI
InChI=1S/C20H35NO4/c1-20(2,3)25-19(24)21-17(18(22)23)16(14-10-6-4-7-11-14)15-12-8-5-9-13-15/h14-17H,4-13H2,1-3H3,(H,21,24)(H,22,23)
InChI Key
ACUROTZKSJCGCE-UHFFFAOYSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(C(C1CCCCC1)C2CCCCC2)C(=O)O

N-α-(t-Butoxycarbonyl)-β,β-dicyclohexyl-DL-alanine, a specialized amino acid derivative, plays a crucial role in peptide synthesis and medicinal chemistry. Here are the applications presented with high perplexity and burstiness:

Peptide Synthesis: Acting as a cornerstone in peptide synthesis, this compound's intricate structure introduces significant steric hindrance profoundly influencing the conformation of peptides. The N-α-protecting group (Boc) strategically shields the amino terminus during stepwise peptide assembly ensuring meticulous peptide construction and preventing unwanted side reactions.

Drug Design and Discovery: By integrating N-α-(t-Butoxycarbonyl)-β,β-dicyclohexyl-DL-alanine into synthetic peptides or small molecules, researchers pave the way for exploring and developing innovative pharmaceuticals. Incorporating this bulky amino acid enables a deep dive into its impact on the biological activity and stability of drug candidates, potentially unveiling more potent and selective therapeutics.

Structural Biology: Playing a pivotal role in unraveling protein folding and dynamics, this compound manipulates peptide interactions and stability, shedding light on the molecular intricacies of proteins. Utilized in model peptides, it serves as a tool to probe the effects of steric hindrance on secondary and tertiary structures, providing valuable insights into the intricate relationships between protein structure and function.

Protease Inhibitor Development: Anchoring the development of protease-resistant peptides, N-α-(t-Butoxycarbonyl)-β,β-dicyclohexyl-DL-alanine is indispensable for creating stable peptide-based drugs. By incorporating this amino acid, scientists engineer analogs that defy enzymatic degradation, extending the therapeutic window of the peptide. This breakthrough holds immense potential for crafting peptide drugs with enhanced pharmacokinetic properties.

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