Fmoc-β-(2-pyridyl)-Ala-OH
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Fmoc-β-(2-pyridyl)-Ala-OH

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Category
Fmoc-Amino Acids
Catalog number
BAT-007499
CAS number
185379-40-2
Molecular Formula
C23H20N2O4
Molecular Weight
388.42
Fmoc-β-(2-pyridyl)-Ala-OH
IUPAC Name
(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-pyridin-2-ylpropanoic acid
Synonyms
Fmoc-3-(2'-pyridyl)-L-alanine
Appearance
White powder
Purity
≥ 99% (HPLC, Chiral Purity)
Density
1.2692 g/cm3
Melting Point
151 °C
Boiling Point
514.13°C
Storage
Store at 2-8 °C
InChI
InChI=1S/C23H20N2O4/c26-22(27)21(13-15-7-5-6-12-24-15)25-23(28)29-14-20-18-10-3-1-8-16(18)17-9-2-4-11-19(17)20/h1-12,20-21H,13-14H2,(H,25,28)(H,26,27)/t21-/m0/s1
InChI Key
DXIVJCDZOMUITR-NRFANRHFSA-N
Canonical SMILES
C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CC4=CC=CC=N4)C(=O)O

Fmoc-β-(2-pyridyl)-Ala-OH, a modified amino acid with versatile properties, finds diverse applications in the realm of bioscience. Here are the key applications presented with a high degree of perplexity and burstiness:

Peptide Synthesis: At the core of solid-phase peptide synthesis (SPPS) lies the widespread use of Fmoc-β-(2-pyridyl)-Ala-OH. Its distinct structure seamlessly integrates into peptide chains, impacting their conformation and biological functionality. This exceptional feature makes it indispensable for crafting peptides with tailored functional and structural attributes, catering to both research and therapeutic endeavors.

Protease Inhibitor Design: The pyridyl group within Fmoc-β-(2-pyridyl)-Ala-OH plays a pivotal role in the design of potent protease inhibitors. By engaging with the active sites of proteases, this unique group leads to robust inhibition. Researchers harness these customized peptides to delve into protease functionalities and advance the development of potential therapeutic agents for combating diseases such as cancer and viral infections.

Protein Interaction Studies: Introducing Fmoc-β-(2-pyridyl)-Ala-OH into peptides opens up avenues for probing intricate protein-protein interactions. Through the incorporation of this modified amino acid, researchers can introduce specialized binding motifs that either enhance or disrupt protein interactions. This application stands as a critical pillar for unraveling molecular mechanisms and screening small molecule inhibitors effectively.

Pharmacokinetics Modulation: Peptides enriched with Fmoc-β-(2-pyridyl)-Ala-OH emerge as potent tools for modulating the pharmacokinetic profiles of therapeutic peptides. Leveraging the influence of the pyridyl group, these peptides exhibit alterations in stability, solubility, and membrane permeability. This capability fuels the development of peptide-based drugs with heightened efficacy, improved bioavailability, and targeted delivery mechanisms.

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