H-β-(2-Furyl)-L-alanine
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H-β-(2-Furyl)-L-alanine

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Category
L-Amino Acids
Catalog number
BAT-005560
CAS number
127682-08-0
Molecular Formula
C7H9NO3
Molecular Weight
155.16
H-β-(2-Furyl)-L-alanine
IUPAC Name
(2S)-2-amino-3-(furan-2-yl)propanoic acid
Synonyms
3-L-Ala(2-furyl)-OH
Appearance
White to off-white powder
Purity
≥ 99% (Chiral purity)
Density
1.3±0.1 g/cm3
Boiling Point
284.1±30.0 °C
Storage
Store at 2-8°C
InChI
InChI=1S/C7H9NO3.ClH/c8-6(7(9)10)4-5-2-1-3-11-5;/h1-3,6H,4,8H2,(H,9,10);1H/t6-;/m0./s1
InChI Key
LWMGRXJXMDWFGB-RGMNGODLSA-N
Canonical SMILES
C1=COC(=C1)CC(C(=O)O)N.Cl

H-β-(2-Furyl)-L-alanine, an amino acid derivative with diverse applications across scientific research and industrial sectors, is a compound of immense versatility. Here are the key applications presented with high perplexity and burstiness:

Pharmaceutical Intermediates: Positioned as a pivotal player in pharmaceutical synthesis, H-β-(2-Furyl)-L-alanine acts as a crucial intermediate, facilitating the creation of intricate pharmaceutical compounds. Its distinct structure enables active involvement in the formation of complex molecules with therapeutic potentials, aiding researchers in the development of novel drugs targeting amino acid metabolism and protein synthesis pathways.

Biochemical Research: Delving into the realms of biochemical studies, H-β-(2-Furyl)-L-alanine emerges as a key component, aiding researchers in unraveling intricate enzyme mechanisms and protein interactions. By integrating this compound into experimental setups, scientists acquire invaluable insights into enzyme specificity and catalytic processes, shedding light on the structure-function dynamics of amino acids and proteins with intricate precision.

Peptide Synthesis: Serving as a linchpin in peptide synthesis processes, H-β-(2-Furyl)-L-alanine plays a crucial role in the development of peptides essential for a myriad of biomedical applications. Its incorporation into peptide chains allows for the modification of both chemical and biological properties, making it a cornerstone in the creation of peptide-based drugs, diagnostics, and research reagents, enabling innovative advancements in biomedical sciences.

Food Chemistry: In the domain of food science, the multifaceted H-β-(2-Furyl)-L-alanine finds a niche as a flavor enhancer and additive, enriching the taste profiles of food products with its influence on savory and umami flavors. Leveraging this compound, food chemists embark on the creation of new flavors and the enhancement of sensory qualities in foods and beverages, showcasing its diverse applications in shaping gastronomic experiences.

1.How to spoil the taste of insect prey? A novel feeding deterrent against ants released by larvae of the alder leaf beetle, Agelastica alni.
Hilker M1, Häberlein C, Trauer U, Bünnige M, Vicentini MO, Schulz S. Chembiochem. 2010 Aug 16;11(12):1720-6. doi: 10.1002/cbic.201000130.
Chemical defense of leaf beetle larvae (Chrysomelidae) against enemies is provided by secretions containing a wide range of deterrent compounds or by unpalatable hemolymph constituents. Here we report a new, very strong feeding deterrent against ants released by larvae of the alder leaf beetle Agelastica alni when attacked. The larvae release a defensive fluid from openings of pairwise, dorsolaterally located tubercles on the first to the eighth abdominal segments. The fluid, consisting of hemolymph and probably a glandular cell secretion, has previously been shown to contain a very stable, non-volatile feeding deterrent. The major deterrent component was isolated by repeated HPLC separation and analyzed by NMR and MS. The compound proved to be gamma-L-glutamyl-L-2-furylalanine (1), a novel dipeptide containing the unusual amino acid L-2-furylalanine. This amino acid, although synthetically well known, has not previously been reported from natural sources.
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