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
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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