Fmoc-3-styryl-D-alanine
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Fmoc-3-styryl-D-alanine

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Category
Fmoc-Amino Acids
Catalog number
BAT-007357
CAS number
215190-23-1
Molecular Formula
C26H23NO4
Molecular Weight
413.47
Fmoc-3-styryl-D-alanine
IUPAC Name
(E,2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-phenylpent-4-enoic acid
Synonyms
Fmoc-D-Ala(styryl)-OH; (R)-2-(Fmoc-amino)-5-phenyl-4-pentenoic acid
Related CAS
159610-82-9 (L-isomer)
Appearance
White amorphous powder
Purity
≥ 99% (HPLC)
Density
1.3±0.1 g/cm3
Melting Point
114-118 °C
Boiling Point
651.0±55.0 °C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C26H23NO4/c28-25(29)24(16-8-11-18-9-2-1-3-10-18)27-26(30)31-17-23-21-14-6-4-12-19(21)20-13-5-7-15-22(20)23/h1-15,23-24H,16-17H2,(H,27,30)(H,28,29)/b11-8+/t24-/m1/s1
InChI Key
ZFMHHKMOLFNMMV-NOENIZQJSA-N
Canonical SMILES
C1=CC=C(C=C1)C=CCC(C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24

Fmoc-3-styryl-D-alanine, a synthetic amino acid derivative commonly utilized in peptide synthesis and pharmaceutical research, boasts versatile applications. Here are the key applications presented with high perplexity and burstiness:

Peptide Synthesis: A pivotal player in solid-phase peptide synthesis, Fmoc-3-styryl-D-alanine serves as a foundational unit, enabling the integration of non-natural amino acids into peptide sequences. This innovation allows for the creation of peptides with distinctive attributes. The Fmoc group provides a shield during synthesis, easily removable under gentle conditions, streamlining the synthetic process.

Antimicrobial Peptides: Harnessing the potential of Fmoc-3-styryl-D-alanine, researchers pioneer the development of novel antimicrobial peptides endowed with heightened efficacy and durability. By incorporating this bulky, hydrophobic residue, peptides acquire enhanced resistance against enzymatic breakdown. These peptides exhibit the ability to target and disrupt microbial cell membranes, presenting promising therapeutic prospects against resilient bacterial strains.

Structural Biology: With modifications involving Fmoc-3-styryl-D-alanine, scientists delve into the realm of protein-protein interactions and conformational alterations. The styryl group, acting as a fluorescing agent, facilitates real-time monitoring of peptide dynamics in solution or cellular milieu. This unique property proves invaluable for investigating peptide behavior in diverse biological contexts.

Drug Development: In the landscape of pharmaceutical innovation, Fmoc-3-styryl-D-alanine emerges as a catalyst for crafting peptidomimetics that elevate the drug-like attributes of therapeutic candidates. Leveraging the distinct chemical traits of this amino acid derivative, researchers enhance the pharmacokinetics and bioavailability of peptide-based medicinal compounds. Moreover, it aids in the exploration of novel scaffolds for advancing drug discovery endeavors.

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