N-α-(9-Fluorenylmethoxycarbonyl)-β-(2-anthryl)-D-alanine
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N-α-(9-Fluorenylmethoxycarbonyl)-β-(2-anthryl)-D-alanine

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Category
Fmoc-Amino Acids
Catalog number
BAT-001812
CAS number
1391555-74-0
Molecular Formula
C32H25NO4
Molecular Weight
487.56
IUPAC Name
(2R)-3-anthracen-2-yl-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
Synonyms
N-alpha-(9-Fluorenylmethoxycarbonyl)-beta-(2-anthryl)-D-alanine; Fmoc-D-Ala(2-Anth)-OH
InChI
InChI=1S/C32H25NO4/c34-31(35)30(16-20-13-14-23-17-21-7-1-2-8-22(21)18-24(23)15-20)33-32(36)37-19-29-27-11-5-3-9-25(27)26-10-4-6-12-28(26)29/h1-15,17-18,29-30H,16,19H2,(H,33,36)(H,34,35)/t30-/m1/s1
InChI Key
CYQGAAWWCDXJIK-SSEXGKCCSA-N
Canonical SMILES
C1=CC=C2C=C3C=C(C=CC3=CC2=C1)CC(C(=O)O)NC(=O)OCC4C5=CC=CC=C5C6=CC=CC=C46

N-α-(9-Fluorenylmethoxycarbonyl)-β-(2-anthryl)-D-alanine, commonly known as Fmoc-Anth-D-Ala, is a specialized chemical compound with diverse applications in bioscience. Here are the key applications presented with high perplexity and burstiness:

Peptide Synthesis: Serving a critical role in solid-phase peptide synthesis (SPPS), N-α-(9-Fluorenylmethoxycarbonyl)-β-(2-anthryl)-D-alanine functions as a protected amino acid derivative. The Fmoc group strategically shields the amine function during the incremental chain elongation process, ensuring precise integration of the amino acid into the evolving peptide chain. This meticulous approach facilitates the production of high-fidelity peptides with exceptional accuracy and structural integrity.

Fluorescence Studies: Harnessing the power of its anthryl group, N-α-(9-Fluorenylmethoxycarbonyl)-β-(2-anthryl)-D-alanine serves as a potent fluorescent probe in biochemical investigations. This unique capability allows researchers to monitor the amino acid's incorporation into peptides and proteins, enabling detailed explorations of protein structure, folding dynamics, and molecular interactions. Particularly valuable in probing protein complexes and uncovering conformational changes, this compound opens new vistas in the field of fluorescence-based studies.

Pharmaceutical Development: By incorporating N-α-(9-Fluorenylmethoxycarbonyl)-β-(2-anthryl)-D-alanine into peptide-based drug candidates, researchers can significantly enhance their stability and bioavailability. The anthryl moiety serves to amplify hydrophobic interactions, bolstering the peptide's binding affinity to its target molecular partners. This unique feature holds great promise in advancing peptide therapeutics for a wide range of ailments, including cancer, diabetes, and infectious diseases, revolutionizing the landscape of pharmaceutical science.

Material Science: In the realm of material science, N-α-(9-Fluorenylmethoxycarbonyl)-β-(2-anthryl)-D-alanine plays a crucial role in the design and synthesis of cutting-edge biomaterials. By integrating this compound into polymer chains, researchers can engineer materials with tailored properties, such as enhanced biocompatibility and mechanical strength. These sophisticated biomaterials find applications in diverse areas, including tissue engineering, drug delivery systems, and medical implants, ushering in a new era of innovation in material science and biotechnology.

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