N-α-(t-Butoxycarbonyl)-β-(2-anthryl)-D-alanine
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N-α-(t-Butoxycarbonyl)-β-(2-anthryl)-D-alanine

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Category
BOC-Amino Acids
Catalog number
BAT-003179
CAS number
1213943-80-6
Molecular Formula
C22H23NO4
Molecular Weight
365.43
IUPAC Name
(2R)-3-anthracen-2-yl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
Synonyms
Boc-D-Ala(2-Anth)-OH
Purity
95%
InChI
InChI=1S/C22H23NO4/c1-22(2,3)27-21(26)23-19(20(24)25)11-14-8-9-17-12-15-6-4-5-7-16(15)13-18(17)10-14/h4-10,12-13,19H,11H2,1-3H3,(H,23,26)(H,24,25)/t19-/m1/s1
InChI Key
VDRHOOVNFURBFF-LJQANCHMSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CC1=CC2=CC3=CC=CC=C3C=C2C=C1)C(=O)O

N-α-(t-Butoxycarbonyl)-β-(2-anthryl)-D-alanine, a specialized chemical compound utilized across diverse scientific domains, offers multifaceted applications. Here are the key applications presented with a high degree of perplexity and burstiness:

Peptide Synthesis: Central to solid-phase peptide synthesis, N-α-(t-Butoxycarbonyl)-β-(2-anthryl)-D-alanine functions as a protected amino acid safeguarding the amino function with the t-Butoxycarbonyl (Boc) group. This protective measure prevents undesirable reactions during synthesis ensuring the integrity of the final peptide structure post-synthesis by facilitating the facile removal of the Boc group.

Fluorescence Studies: The anthryl group within N-α-(t-Butoxycarbonyl)-β-(2-anthryl)-D-alanine acts as a potent fluorescent probe in molecular and cellular biology experiments. Leveraging its inherent fluorescence, researchers delve into real-time investigations of protein interactions folding dynamics and cellular processes. This compound's intrinsic fluorescence capability offers a seamless approach to monitoring biological phenomena obviating the need for additional labeling steps.

Structural Biology: In the domain of structural biology, this compound serves as a tool for introducing specific protein modifications enabling comprehensive analyses of protein structure and function. The anthryl group also functions as a pivotal reporter group in techniques like nuclear magnetic resonance (NMR) shedding light on conformational dynamics and protein interactions thereby enriching our understanding of protein behavior.

Synthetic Biology: Embracing synthetic biology, N-α-(t-Butoxycarbonyl)-β-(2-anthryl)-D-alanine finds applications in protein engineering to confer novel functionalities. By integrating non-natural amino acids like this compound into proteins, researchers broaden the chemical repertoire of proteins fostering the creation of protein variants with unique attributes and catalytic properties. This diversification enables the development of tailored proteins for diverse applications spanning biocatalysis and therapeutic innovations.

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