Fmoc-3-(4'-pyridyl)-D-alanine
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Fmoc-3-(4'-pyridyl)-D-alanine

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Category
Fmoc-Amino Acids
Catalog number
BAT-007321
CAS number
205528-30-9
Molecular Formula
C23H20N2O4
Molecular Weight
388.42
Fmoc-3-(4'-pyridyl)-D-alanine
IUPAC Name
(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-pyridin-4-ylpropanoic acid
Synonyms
Fmoc-D-Ala(4'-pyridyl)-OH; Fmoc-(R)-2-amino-3-(4'-pyridyl)propanoic acid
Related CAS
169555-95-7 (L-isomer)
Appearance
White powder
Purity
≥ 99% (HPLC)
Density
1.309 g/cm3
Boiling Point
646.9°C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C23H20N2O4/c26-22(27)21(13-15-9-11-24-12-10-15)25-23(28)29-14-20-18-7-3-1-5-16(18)17-6-2-4-8-19(17)20/h1-12,20-21H,13-14H2,(H,25,28)(H,26,27)/t21-/m1/s1
InChI Key
SCSSXJVRZMQUKA-OAQYLSRUSA-N
Canonical SMILES
C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CC4=CC=NC=C4)C(=O)O

Fmoc-3-(4'-pyridyl)-D-alanine is a derivative of the amino acid alanine protected by the Fmoc (9-fluorenylmethyloxycarbonyl) group, and it finds numerous applications in peptide synthesis and biochemical research. Here are some key applications of Fmoc-3-(4'-pyridyl)-D-alanine:

Solid-Phase Peptide Synthesis: Fmoc-3-(4'-pyridyl)-D-alanine is employed in solid-phase peptide synthesis (SPPS) to incorporate modified amino acids into peptides. The Fmoc group provides a temporary protective group that prevents unwanted reactions during the synthesis process. This allows researchers to create peptides with specific sequences for studies in drug development, molecular biology, and biochemistry.

Peptide-Based Drug Development: In pharmaceutical research, Fmoc-3-(4'-pyridyl)-D-alanine is used to design peptide-based drug candidates with enhanced activity and specificity. The inclusion of modified amino acids can improve the stability and bioavailability of peptide drugs. This modification can also provide specific interactions with biological targets, leading to more effective therapeutics.

Structural Biology Studies: Fmoc-3-(4'-pyridyl)-D-alanine is valuable in structural biology for investigating protein-peptide interactions and protein folding. By incorporating this modified amino acid into peptides, researchers can probe the structural and functional roles of specific residues in proteins. This helps in understanding the mechanisms underlying protein function and designing inhibitors or modulators.

Chemical Biology: In the field of chemical biology, Fmoc-3-(4'-pyridyl)-D-alanine is used to study protein modification and signaling pathways. The pyridyl side chain can be employed to introduce reactive groups for subsequent chemical modifications or bioconjugation. This versatility enables the study of dynamic biological processes and the development of novel biochemical tools and probes.

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