Boc-3-(2-naphthyl)-L-alanine
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Boc-3-(2-naphthyl)-L-alanine

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Boc-3-(2-naphthyl)-L-alanine functions as a reagent for the synthesis of dipeptidyl nitriles as potent and reversible inhibitors of Cathepsin C.

Category
BOC-Amino Acids
Catalog number
BAT-007959
CAS number
58438-04-3
Molecular Formula
C18H21NO4
Molecular Weight
315.36
Boc-3-(2-naphthyl)-L-alanine
IUPAC Name
(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-naphthalen-2-ylpropanoic acid
Synonyms
Boc-L-Ala(2-naphthyl)-OH; Boc-2-Nal-OH; N-(tert-Butoxycarbonyl)-3-(2-naphthyl)-L-alanine; Boc-3-(2 naphthyl)-L-alanine; BOC-2-L-NAPHTHYLALANINE; (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(naphthalen-2-yl)propanoic acid; Boc-L-2-Naphthylalanine; N-Boc-3-(2-naphthyl)-L-alanine; (S)-2-((tert-butoxycarbonyl)amino)-3-(naphthalen-2-yl)propanoic acid
Appearance
White to off-white powder
Purity
≥ 99.5% (Chiral HPLC)
Density
1.200 g/cm3
Melting Point
92-95 °C
Boiling Point
512.2 °C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C18H21NO4/c1-18(2,3)23-17(22)19-15(16(20)21)11-12-8-9-13-6-4-5-7-14(13)10-12/h4-10,15H,11H2,1-3H3,(H,19,22)(H,20,21)/t15-/m0/s1
InChI Key
URKWHOVNPHQQTM-HNNXBMFYSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CC1=CC2=CC=CC=C2C=C1)C(=O)O

Boc-3-(2-naphthyl)-L-alanine, a crucial compound in peptide synthesis and diverse biochemical applications, boasts a spectrum of key utilities. Here are four primary applications presented with heightened perplexity and burstiness:

Peptide Synthesis: Embedded within the realm of peptide synthesis, Boc-3-(2-naphthyl)-L-alanine stands tall as a fundamental building block. Its structural intricacies, including the prominent naphthyl group, play a pivotal role in crafting peptides with elevated stability and specificity. This compound finds extensive application in generating peptides tailored for both research and therapeutic endeavors, highlighting its versatility in peptide science.

Protease Inhibitor Studies: Foraying into the domain of biochemical research, Boc-3-(2-naphthyl)-L-alanine emerges as a key player in probing protease inhibitors. Eminent for its bulky naphthyl moiety, this compound serves as a valuable tool in unraveling enzyme-substrate interactions. Researchers leverage its properties to decipher the mechanisms of protease inhibitors, paving the way for novel drug development targeting afflictions like cancer and HIV, ushering in a new era of therapeutic innovation.

Protein Engineering: Delving into the realm of protein manipulation, Boc-3-(2-naphthyl)-L-alanine shines as a catalyst for altering protein characteristics. By incorporating this compound into protein sequences, scientists can fine-tune protein folding dynamics, stability, and functionality. This methodological approach plays a pivotal role in engineering proteins endowed with enhanced therapeutic or industrial attributes, showcasing the transformative power of protein design in diverse applications.

Chemical Biology: Anchored in the arena of chemical biology, Boc-3-(2-naphthyl)-L-alanine assumes a pivotal role in crafting bioactive molecular entities. Its integration into diverse molecular architectures facilitates the synthesis of compounds with precise biological functionalities. Researchers harness the potential of this compound to fabricate inhibitors, probes, and other bioactive molecules that serve as key tools for interrogating complex biological systems, underscoring its significance in unraveling the intricacies of life's molecular tapestry.

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