N-α-(t-Butoxycarbonyl)-β-(1-pyrenyl)-L-alanine
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N-α-(t-Butoxycarbonyl)-β-(1-pyrenyl)-L-alanine

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Category
BOC-Amino Acids
Catalog number
BAT-003178
CAS number
100442-89-5
Molecular Formula
C24H23NO4
Molecular Weight
389.44
N-α-(t-Butoxycarbonyl)-β-(1-pyrenyl)-L-alanine
IUPAC Name
(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-pyren-1-ylpropanoic acid
Synonyms
Boc-Ala(1-Pyn)-OH; Boc-Ala(1-Pyrenyl)-OH; BOC-3-(1-PYRENYL)-L-ALANINE; 2,2-dimethylpropanoic hydrazide; tert-butoxycarbonyl hydrazine; Pivalic acid,hydrazide
Purity
95%
Density
1.293±0.060 g/cm3
Boiling Point
614.8±48.0 °C
InChI
InChI=1S/C24H23NO4/c1-24(2,3)29-23(28)25-19(22(26)27)13-17-10-9-16-8-7-14-5-4-6-15-11-12-18(17)21(16)20(14)15/h4-12,19H,13H2,1-3H3,(H,25,28)(H,26,27)/t19-/m0/s1
InChI Key
JDYATIJHVFTYFG-IBGZPJMESA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CC1=C2C=CC3=CC=CC4=C3C2=C(C=C4)C=C1)C(=O)O

N-α-(t-Butoxycarbonyl)-β-(1-pyrenyl)-L-alanine, a modified amino acid central to biochemistry and molecular biology, finds diverse applications in the scientific arena. Here are the key applications presented with high perplexity and burstiness:

Fluorescence Studies: Serving as a vibrant fluorescent probe in biochemical assays, this compound's pyrene moiety enables the visualization and tracking of molecular interactions. It proves invaluable for exploring protein folding conformational changes and intricate intracellular processes through its unique fluorescence properties.

Peptide Synthesis: N-α-(t-Butoxycarbonyl)-β-(1-pyrenyl)-L-alanine plays a pivotal role in solid-phase peptide synthesis. The t-butoxycarbonyl (Boc) protecting group streamlines the stepwise assembly of peptides, safeguarding amino groups from undesired reactions. This method allows for the construction of elaborate peptide sequences tailored for both research and therapeutic applications.

Protein Labeling: Harnessing the fluorescent nature of this modified amino acid, scientists utilize it for precise protein labeling. Integration into protein structures enables the exploration of dynamics localization and interactions within cellular environments. This illuminates essential facets of protein function and propels the advancement of fluorescence-based detection methodologies.

Molecular Probes: Functioning as a versatile molecular probe, N-α-(t-Butoxycarbonyl)-β-(1-pyrenyl)-L-alanine is instrumental in elucidating lipid and membrane dynamics. Its hydrophobic pyrene group seamlessly inserts into lipid membranes enabling researchers to monitor shifts in membrane structure and surrounding environments. This capability holds significance in unraveling membrane-associated processes and related disorders, offering valuable insights into cellular physiology.

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