γ-(2-Furyl)-D-β-homoalanine
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γ-(2-Furyl)-D-β-homoalanine

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Category
β−Amino Acids
Catalog number
BAT-007539
CAS number
270596-32-2
Molecular Formula
C8H11NO3
Molecular Weight
169.18
γ-(2-Furyl)-D-β-homoalanine
IUPAC Name
(3R)-3-amino-4-(furan-2-yl)butanoic acid
Synonyms
H-D-Ala(2-Furyl)-(C#CH2)OH; (R)-3-Amino-4-(2-furyl)butanoic acid; (R)-3-AMINO-4-(2-FURYL)BUTANOIC ACID; (R)-3-amino-4-(furan-2-yl)butanoic acid; (R)-beta-Furfuryl-beta-alanine; H-D-Ala(2-Furyl)-(C#CH2)OH; (3R)-3-amino-4-(furan-2-yl)butanoic acid
Purity
≥ 98% (Chiral purity)
Density
1.237 g/cm3
Boiling Point
306.5 °C at 760 mmHg
InChI
InChI=1S/C8H11NO3/c9-6(5-8(10)11)4-7-2-1-3-12-7/h1-3,6H,4-5,9H2,(H,10,11)/t6-/m1/s1
InChI Key
ZIAIKPBTLUWDMG-ZCFIWIBFSA-N
Canonical SMILES
C1=COC(=C1)CC(CC(=O)O)N

γ-(2-Furyl)-D-β-homoalanine, an extraordinary amino acid with diverse potential applications across scientific domains owing to its distinct chemical composition. Here are four significant applications of γ-(2-Furyl)-D-β-homoalanine portrayed with heightened perplexity and burstiness:

Drug Development: Serving as a fundamental component for synthesizing novel pharmaceuticals, γ-(2-Furyl)-D-β-homoalanine offers a platform for enhancing the bioavailability and efficacy of drug candidates. By incorporating this unique amino acid into peptide-based drugs, researchers can delve into its therapeutic potentials, unveiling new avenues for drug discovery and development.

Peptide Engineering: Amidst biochemical inquiries, γ-(2-Furyl)-D-β-homoalanine emerges as a valuable asset for crafting peptides with unprecedented attributes. Its integration into peptide sequences not only bolsters stability but also amplifies binding affinity and specificity towards specific targets, catalyzing the advancement of cutting-edge biomedical applications, encompassing biomaterials and biosensors.

Protein Structure Studies: In quests to unravel the intricacies of protein structure and function, γ-(2-Furyl)-D-β-homoalanine plays a pivotal role. By strategically substituting this amino acid at precise locations within proteins, researchers embark on a journey to decipher its influence on protein folding, stability, and activity, shedding light on the significance of individual residues in dictating protein behaviors.

Chemistry and Materials Science: Embarking on the synthesis of innovative polymers and materials, γ-(2-Furyl)-D-β-homoalanine emerges as a key player, courtesy of its unique furan ring and amino acid backbone. Scientists can explore its incorporation into polymer chains, sculpting materials endowed with exceptional mechanical and chemical properties, heralding breakthroughs in the realm of advanced materials for industrial and technological applications.

1. N-glycosides of amino acid amides from Hemerocallis fulva var. sempervirens
Yuko Ogawa, Tenji Konishi Chem Pharm Bull (Tokyo). 2009 Oct;57(10):1110-2. doi: 10.1248/cpb.57.1110.
As part of our search for sedative substances from natural sources, we isolated two novel amino acid amides connected with the fructopyranose, kwansonine A (1) and kwansonine B (2), together with three known amino acid amides, longitubanine A (3), longitubanine B (4), and pinnatanine (5), from Hemerocallis fulva L. var. sempervirens (ARAKI) M. HOTTA. The structures of 1 and 2 have been determined on the spectroscopic evidences as N(2)-(1-beta-D-fructopyranosyl)-N(5)-(2',5'-dihydro-2'-furyl-3'-hydroxymethyl)-gamma-hydroxyglutamine and N(2)-(1-beta-D-fructopyranosyl)-N(5)-(2-hydroxymethylbutadienyl)-gamma-hydroxyglutamine. This is the first report on the isolation of amino acid amide N-furctoside from Hemerocallis genus plant.
2. The mutagenic activity of 61 agents as determined by the micronucleus, Salmonella, and sperm abnormality assays
W R Bruce, J A Heddle Can J Genet Cytol. 1979 Sep;21(3):319-34. doi: 10.1139/g79-036.
A comparison of two rapid and inexpensive in vivo mammalian assays and the Ames Salmonella assay is presented for 61 agents; Acetylsalicylic acid; Acriflavine; Actinomycin D; 2(2-furyl)-3-(5-nitro-2-furyl)acrylamide (AF-2); Aflatoxin B1; 2-aminofluorene; Aminopterin; Aroclor 1254; Ascorbic acid; Azathioprine; Benzo(a)pyrene; 5-Bromo-2'-deoxyuridine; Busulphan, Butylated hydroxytoluene; Cadmium chloride; Caffeine; Calcium cyclamate; Chloral hydrate; Chloromycetin succinate; Codeine phosphate, Colchicine; Cycloheximide; Cyclophosphamide; DDT; 2,4-Diaminoanisole; Dibutylnitrosamine; 9, 10 Dimethyl-1,2-benzanthracene; 1,1-Dimethylhydrazine; Dimethylnitrosamine; Epinephrine; Ethyl methane sulphonate (EMS); 2-formylamino-4-(5-nitro-2-furyl)thiazole (FANFT); 2-(2-formylhydrazino)-4-(5-nitro-2-furyl)thiazole (FNT); Glucose, Griseofulvin; Hycanthone methane sulphonate; Hydroxyurea; 5-Iodo-2'-deoxyuridine; Lead acetate; Mechlorethamine; 3-Methylcholanthrene; Methyl mercury acetate; Methyl methane sulfonate (MMS); N-methyl-N-nitro-N'-nitrosoguanidine; Mitomycin C; Monosodium glutamate; 1-Naphthalamine; 2-Naphthalamine; Nitrofurazone; 4-Nitro-O-phenylene diamine; 4-Nitro-quinoline-1-oxide (4-NQO); Phenobarbitone; Procarbazine; Quinacrine dihydrochloride; Radiation (gamma-rays); Sodium chloride; Triethylene thiophosphoramide; Trimethyl phosphate; Tris(2-methyl-1-arizidinyl) phosphine oxide; Urethan; Vinblastine. The results support the concept of multiple assays for mutagenicity and show that some combinations of assays are superior to others.
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