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

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Category
Fmoc-Amino Acids
Catalog number
BAT-001814
CAS number
1263047-16-0
Molecular Formula
C25H20N2O4S
Molecular Weight
444.51
IUPAC Name
(2R)-3-(1,3-benzothiazol-2-yl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
Synonyms
(2R)-3-(1,3-benzothiazol-2-yl)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}propanoic acid; Fmoc-D-Ala(2-Bztz)-OH; Fmoc-D-Ala(2-Benzothiazolyl)-OH
Purity
99%
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-/m1/s1
InChI Key
FOEQAVDISWFCSU-OAQYLSRUSA-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)-D-alanine, also recognized as Fmoc-β-Bth-D-Ala, stands as a specialized amino acid derivative utilized in peptide synthesis and biochemical research. Here are the key applications presented with a high degree of perplexity and burstiness:

Peptide Synthesis: Engaging Fmoc-β-Bth-D-Ala in solid-phase peptide synthesis plays a pivotal role in constructing intricate peptide chains. This compound, serving as a shielded amino acid, enables the sequential inclusion of amino acids crucial for the development of peptide-based medications, vaccines, and investigative instruments.

Protein Engineering: Within the realm of protein engineering, the integration of this compound into proteins allows for the introduction of specific functional groups or sites. By amalgamating Fmoc-β-Bth-D-Ala into protein sequences, researchers can explore protein structure, function, and interactions, ultimately facilitating the creation of enhanced or novel proteins.

Fluorescence Labeling: N-α-(9-Fluorenylmethoxycarbonyl)-β-(2-benzo[b]thiazolyl)-D-alanine proves invaluable for fluorescence labeling of peptides and proteins. With its fluorescent benzo[b]thiazolyl group, it becomes a pertinent tool for monitoring and imaging endeavors in biochemical and cellular domains. This application greatly aids in the examination of protein dynamics and localization within living cells.

Drug Discovery: Integral to the realm of drug discovery and development, particularly in the formulation of peptide-based inhibitors and probes, Fmoc-β-Bth-D-Ala serves a significant role. By introducing this derivative into peptide sequences, researchers can craft specialized compounds targeting specific biological pathways. This process not only expedites the discovery of potential therapeutic candidates but also facilitates in-depth exploration of their modes of action.

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