Fmoc-3-(3'-pyridyl)-D-alanine
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Fmoc-3-(3'-pyridyl)-D-alanine

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Category
Fmoc-Amino Acids
Catalog number
BAT-007319
CAS number
142994-45-4
Molecular Formula
C23H20N2O4
Molecular Weight
388.42
Fmoc-3-(3'-pyridyl)-D-alanine
IUPAC Name
(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-pyridin-3-ylpropanoic acid
Synonyms
Fmoc-D-Ala(3'-pyridyl)-OH; Fmoc-(R)-2-amino-3-(3'-pyridyl)propanoic acid
Related CAS
175453-07-3 (L-isomer)
Appearance
White crystalline powder
Purity
≥ 99% (HPLC)
Density
1.309 g/cm3
Melting Point
164-169 °C
Boiling Point
645.6°C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C23H20N2O4/c26-22(27)21(12-15-6-5-11-24-13-15)25-23(28)29-14-20-18-9-3-1-7-16(18)17-8-2-4-10-19(17)20/h1-11,13,20-21H,12,14H2,(H,25,28)(H,26,27)/t21-/m1/s1
InChI Key
JQLPMTXRCLXOJO-OAQYLSRUSA-N
Canonical SMILES
C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CC4=CN=CC=C4)C(=O)O

Fmoc-3-(3'-pyridyl)-D-alanine, a derivative of alanine combining a pyridine ring and an Fmoc protecting group, finds diverse applications in various fields. Here are the key applications presented with high perplexity and burstiness:

Peptide Synthesis: A cornerstone in solid-phase peptide synthesis, Fmoc-3-(3'-pyridyl)-D-alanine acts as a crucial building block, thanks to the Fmoc group's role in temporarily safeguarding the amino group during peptide elongation. This strategic protection prevents premature reactions, ensuring the peptide's integrity and sequence fidelity are preserved throughout the synthesis process.

Structure-Activity Relationship Studies: By integrating Fmoc-3-(3'-pyridyl)-D-alanine into peptides or protein sequences, researchers embark on a fascinating journey exploring how alterations in amino acid structure influence biological activity. The unique pyridyl ring appended to the alanine residue engages with biological targets, offering valuable insights into molecular interactions and binding affinities. Such investigations are fundamental for advancing drug discovery efforts and designing bioactive compounds with precision.

Pharmaceutical Development: With its exceptional structural characteristics, Fmoc-3-(3'-pyridyl)-D-alanine emerges as a valuable asset in shaping pharmaceutical peptides and peptidomimetics. Its incorporation elevates the stability, bioavailability, and specificity of therapeutic peptides, empowering researchers to engineer novel drugs with enhanced pharmacological profiles. Leveraging these distinct attributes, scientists pave the way for innovative advancements in pharmaceutical development.

Molecular Probes and Diagnostics: Harnessing the potential of Fmoc-3-(3'-pyridyl)-D-alanine, researchers forge fluorescent or radiolabeled probes tailored for diagnostic applications. The pyridyl group's presence facilitates specific interactions with target molecules or receptors, streamlining detection and imaging processes. This capability proves invaluable in dissecting biological processes and unraveling disease states in real-time, thus propelling advancements in molecular diagnostics and probing.

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