N-α-(9-Fluorenylmethoxycarbonyl)-β-cyano-D-alanine
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N-α-(9-Fluorenylmethoxycarbonyl)-β-cyano-D-alanine

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Category
Fmoc-Amino Acids
Catalog number
BAT-001819
CAS number
1820575-73-2
Molecular Formula
C19H16N2O4
Molecular Weight
336.35
IUPAC Name
(2R)-3-cyano-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
Synonyms
(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-cyanopropanoic acid; Fmoc-D-Ala(3-CN)-OH; Fmoc-D-Ala(β-CN)-OH
InChI
InChI=1S/C19H16N2O4/c20-10-9-17(18(22)23)21-19(24)25-11-16-14-7-3-1-5-12(14)13-6-2-4-8-15(13)16/h1-8,16-17H,9,11H2,(H,21,24)(H,22,23)/t17-/m1/s1
InChI Key
FJSOTHAUCCEZLI-QGZVFWFLSA-N
Canonical SMILES
C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CC#N)C(=O)O

N-α-(9-Fluorenylmethoxycarbonyl)-β-cyano-D-alanine (Fmoc-β-cyano-D-alanine) stands as a prized compound with diverse applications in the realms of biochemistry and pharmaceuticals. Here are the key applications of this invaluable compound, presented with high perplexity and burstiness:

Peptide Synthesis: Integral to solid-phase peptide synthesis (SPPS), Fmoc-β-cyano-D-alanine finds widespread use due to its amino group protection. By incorporating this amino acid, researchers unlock the ability to synthesize peptides enriched with beta-amino acids, thus enhancing their stability and bioactivity. This process plays a pivotal role in advancing the frontier of novel peptide-based therapeutics and cutting-edge research tools.

Enzyme Inhibition Studies: Within the realm of enzyme inhibition, Fmoc-β-cyano-D-alanine emerges as a key player in the design of enzyme inhibitors, particularly targeting enzymes involved in amino acid metabolism. Through the strategic introduction of this residue into peptides or small molecules, researchers can delve into binding affinities and inhibitory mechanisms, propelling the discovery of groundbreaking drugs aimed at combatting metabolic and infectious diseases.

Structural Biology: In the intricate field of structural biology, Fmoc-β-cyano-D-alanine holds significant importance for unravelling the mysteries of protein folding and stability. With its distinctive structural properties, scientists can craft peptide analogs mirroring natural proteins, shedding light on protein-protein interactions and folding pathways. This deepens our comprehension of disease mechanisms and facilitates the development of therapeutic proteins, marking a leap forward in the biopharmaceutical landscape.

Proteomics Research: A linchpin in the realm of proteomics, Fmoc-β-cyano-D-alanine serves as a vital tool for generating precise peptide markers tailored for mass spectrometry analysis. Through its incorporation, researchers can effectively label and identify peptides, enabling the comprehensive study of protein expression and modifications. This pivotal role aids in the discovery of biomarkers and the advancement of diagnostic tools, paving the way for innovative approaches in the realm of molecular diagnostics.

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