N-α-(9-Fluorenylmethoxycarbonyl)-β-(2-benzo[b]thiazolyl)-L-alanine
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N-α-(9-Fluorenylmethoxycarbonyl)-β-(2-benzo[b]thiazolyl)-L-alanine

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Category
Fmoc-Amino Acids
Catalog number
BAT-005502
CAS number
959583-56-3
Molecular Formula
C25H20N2O4S
Molecular Weight
444.51
N-α-(9-Fluorenylmethoxycarbonyl)-β-(2-benzo[b]thiazolyl)-L-alanine
IUPAC Name
(2S)-3-(1,3-benzothiazol-2-yl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
Synonyms
Fmoc-Ala(2-Bztz)-OH; Fmoc-Ala(2-Benzothiazolyl)-OH; 2-Benzothiazolepropanoic acid,α-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-, (αS)-; N-α-(9-Fluorenylmethoxycarbonyl)-β-(2-benzo[b]thiazolyl)-L-alanine; FMOC-L-ALA(BTH)-OH; Fmoc-β-(benzothiazol-2-yl)-L-alanine
Appearance
White or off-white solid
Purity
≥ 99.5% (Chiral HPLC)
Density
1.387±0.060 g/cm3
Boiling Point
688.5±55.0 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C25H20N2O4S/c28-24(29)21(13-23-26-20-11-5-6-12-22(20)32-23)27-25(30)31-14-19-17-9-3-1-7-15(17)16-8-2-4-10-18(16)19/h1-12,19,21H,13-14H2,(H,27,30)(H,28,29)/t21-/m0/s1
InChI Key
FOEQAVDISWFCSU-NRFANRHFSA-N
Canonical SMILES
C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CC4=NC5=CC=CC=C5S4)C(=O)O

N-α-(9-Fluorenylmethoxycarbonyl)-β-(2-benzo[b]thiazolyl)-L-alanine, a specialized chemical compound, finds diverse applications in various biochemical settings. Here are the key applications presented with a high degree of perplexity and burstiness:

Solid-Phase Peptide Synthesis (SPPS): An essential component in SPPS, N-α-(9-Fluorenylmethoxycarbonyl)-β-(2-benzo[b]thiazolyl)-L-alanine serves as a protected amino acid residue that facilitates the sequential addition of amino acids. The unique protecting group Fmoc embedded in this compound allows for meticulous deprotection steps, aiding in the intricate synthesis of complex peptides indispensable for cutting-edge research and therapeutic interventions.

Fluorescence Labeling: Harnessing the fluorenylmethoxycarbonyl (Fmoc) group within N-α-(9-Fluorenylmethoxycarbonyl)-β-(2-benzo[b]thiazolyl)-L-alanine enables fluorescence-based studies of peptides. The striking fluorescence exhibited by the Fmoc group enables precise tracking and visualization of peptides in a myriad of biological assays. Leveraging this fluorescent property, researchers can monitor dynamic peptide interactions, precise localization, and cellular/molecular uptake, unraveling intricate biological processes with unprecedented depth.

Protease Inhibition Studies: The intriguing β-(2-benzo[b]thiazolyl) moiety housed in N-α-(9-Fluorenylmethoxycarbonyl)-β-(2-benzo[b]thiazolyl)-L-alanine bears structural similarities to natural protease substrates, rendering it invaluable for investigating protease-substrate interactions and formulating protease inhibitors. Embedding this compound into peptides empowers scientists to dissect how diverse proteases cleave targets, leading to the bespoke design of specific inhibitors to modulate protease activities in disease contexts, unveiling significant therapeutic potential.

Drug Development: In the realm of drug development, N-α-(9-Fluorenylmethoxycarbonyl)-β-(2-benzo[b]thiazolyl)-L-alanine emerges as a pivotal player in crafting novel bioactive peptides for groundbreaking discoveries. Its unique structural attributes pave the way for designing peptides with enhanced stability and sophisticated functionality, offering a promising avenue for generating peptide-based therapeutics with transformative applications in combatting multifarious diseases, from cancer to infectious ailments, through innovative medicinal chemistry approaches.

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