(S)-2-Amino-2-methyl-4-pentenoic acid
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(S)-2-Amino-2-methyl-4-pentenoic acid

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(S)-2-Amino-2-methyl-4-pentenoic acid, an analog of amino acid, serves as a versatile ligand for studying the ionotropic glutamate receptors, besides becoming a precursor for synthesizing diverse natural and unnatural amino acids. With its potential therapeutic effects on neural injury and epilepsy, this compound bears immense significance in the realm of neurological research.

Category
Amino Acids for Stapled Peptide
Catalog number
BAT-006499
CAS number
96886-56-5
Molecular Formula
C6H11NO2
Molecular Weight
129.16
(S)-2-Amino-2-methyl-4-pentenoic acid
Size Price Stock Quantity
100 mg $439 In stock
1 g $999 In stock
IUPAC Name
(2R)-2-amino-2-methylpent-4-enoic acid
Synonyms
L-alpha-Allylalanine; 4-Pentenoicacid,2-amino-2-methyl-,(2R)-(9CI); L-α-Methylallylalanine; (S)-2-Amino-2-methyl-4-pentenoic acid; L-α-ALLYLALANINE; (R)-alpha-Allylalanine (>98%, >98%ee); H-alpha-All-L-Ala-OH; (R)-2-amino-2-methylpent-4-enoic acid
Purity
98%
Density
1.067g/cm3
Boiling Point
226.178°C at 760 mmHg
Storage
Store at RT
InChI
InChI=1S/C6H11NO2/c1-3-4-6(2,7)5(8)9/h3H,1,4,7H2,2H3,(H,8,9)/t6-/m1/s1
InChI Key
QMBTZYHBJFPEJB-ZCFIWIBFSA-N
Canonical SMILES
CC(CC=C)(C(=O)O)N
1.Local and traditional uses, phytochemistry, and pharmacology of Sophora japonica L.: A review.
He X1, Bai Y2, Zhao Z2, Wang X2, Fang J2, Huang L3, Zeng M2, Zhang Q2, Zhang Y2, Zheng X4. J Ethnopharmacol. 2016 Apr 13. pii: S0378-8741(16)30205-7. doi: 10.1016/j.jep.2016.04.014. [Epub ahead of print]
ETHNOPHARMACOLOGICAL RELEVANCE: Sophora japonica (Fabaceae), also known as Huai (Chinese: ), is a medium-sized deciduous tree commonly found in China, Japan, Korea, Vietnam, and other countries. The use of this plant has been recorded in classical medicinal treatises of ancient China, and it is currently recorded in both the Chinese Pharmacopoeia and European Pharmacopoeia. The flower buds and fruits of S. japonica, also known as Flos Sophorae Immaturus and Fructus Sophorae in China, are most commonly used in Asia (especially in China) to treat hemorrhoids, hematochezia, hematuria, hematemesis, hemorrhinia, uterine or intestinal hemorrhage, arteriosclerosis, headache, hypertension, dysentery, dizziness, and pyoderma. To discuss feasible trends for further research on S. japonica, this review highlights the botany, ethnopharmacology, phytochemistry, biological activities, and toxicology of S. japonica based on studies published in the last six decades.
2.Novel N-allyl/propargyl tetrahydroquinolines: Synthesis via three-component cationic imino Diels-Alder reaction, binding prediction and evaluation as cholinesterase inhibitors.
Rodríguez YA1, Gutiérrez M1, Ramírez D2, Alzate-Morales J2, Bernal CC3, Güiza FM3, Romero Bohórquez AR3. Chem Biol Drug Des. 2016 Apr 17. doi: 10.1111/cbdd.12773. [Epub ahead of print]
New N-allyl/propargyl 4-substituted 1,2,3,4-tetrahydroquinolines derivatives were efficiently synthesized using acid-catalyzed three components cationic imino Diels-Alder reaction (70-95%). All compounds were tested in vitro as dual acetylcholinesterase (AChE) and butyryl-cholinesterase (BChE) inhibitors and their potential binding modes, and affinity, were predicted by molecular docking and binding free energy calculations (∆G), respectively. The compound 4af (IC50 = 72 μM) presented the most effective inhibition against AChE despite its poor selectivity (SI= 2), while the best inhibitory activity on BChE was exhibited by compound 4ae (IC50 = 25.58 μM) with considerable selectivity (SI=0.15). Molecular docking studies indicated that the most active compounds fit in the reported AChE and BChE active sites. Moreover, our computational data indicated a high correlation between the calculated ∆G and the experimental activity values in both targets.
3.Antioxidant capacity of different cheeses: Affecting factors and prediction by near infrared spectroscopy.
Revilla I1, González-Martín MI2, Vivar-Quintana AM3, Blanco-López MA3, Lobos-Ortega IA4, Hernández-Hierro JM5. J Dairy Sci. 2016 Apr 13. pii: S0022-0302(16)30171-0. doi: 10.3168/jds.2015-10564. [Epub ahead of print]
In this study, we analyzed antioxidant capacity of 224 cheese samples prepared using 16 varied mixtures of milk from cows, ewes, and goats, in 2 manufacturing seasons (winter and summer), and over 6 mo of ripening. Antioxidant capacity was evaluated using the spectrophotometric 2,2-azinobis(3-ethylenebenzothiazoline-6-sulfonic acid) (ABTS) method. Total antioxidant capacity was significantly correlated with season of manufacturing and time of ripening but not with animal species providing the milk. Moreover, statistically significant correlations between the total antioxidant capacity and retinol (r = 0.399), fat percentage (r = 0.308), protein percentage (r = 0.366), K (r = 0.385), Mg (r = 0.312), Na (r = 0.432), and P (0.272) were observed. We evaluated the use of near infrared spectroscopy technology, together with the use of a remote reflectance fiber-optic probe, to predict the antioxidant capacity of cheese samples. The model generated allowed us to predict antioxidant capacity in unknown cheeses of different compositions and ripening times.
4.Antihyperlipidemic and Antioxidant Activities of Edible Tunisian Ficus carica L. Fruits in High Fat Diet-Induced Hyperlipidemic Rats.
Belguith-Hadriche O1,2, Ammar S3,4, Contreras MD4, Turki M5, Segura-Carretero A4, El Feki A6, Makni-Ayedi F5, Bouaziz M7. Plant Foods Hum Nutr. 2016 Apr 16. [Epub ahead of print]
The phenolic constituents of the aqueous-ethanolic extract of Tunisian Ficus carica (F. carica) fruit (FE) and its antihyperlipidemic and antioxidant activities in high-fat diet-induced hyperlipidemic rats (HFD) were evaluated. The obtained results demonstrated that the FE improved the lipid profile by decreasing the total cholesterol, triglyceride, low-density lipoprotein cholesterol and increasing high-density lipoprotein cholesterol levels. It also reduced the content of thiobarbituric acid-reactive substances and increased the antioxidant enzymes in liver, heart and kidney in HFD-fed rats. These antihyperlipidemic effects and in vivo antioxidative effects correlated with the in vitro phenolic content scavenging ability. Thus, the major phenolic compounds were identified using reversed-phase ultra-high-performance liquid chromatography (RP-UHPLC) coupled with two detection systems: diode-array detection (DAD) and quadrupole time-of-flight (QTOF) mass spectrometry (MS).
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