(2S,4S)-4-Fluoro-pyrrolidine-2-carboxylic acid
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(2S,4S)-4-Fluoro-pyrrolidine-2-carboxylic acid

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(2S,4S)-4-Fluoro-pyrrolidine-2-carboxylic acid is used in the study of stereoelectronic effects on collagen stability.

Category
Fluorinated amino acids
Catalog number
BAT-007764
CAS number
2438-57-5
Molecular Formula
C5H8FNO2
Molecular Weight
133.12
(2S,4S)-4-Fluoro-pyrrolidine-2-carboxylic acid
IUPAC Name
(2S,4S)-4-fluoropyrrolidine-2-carboxylic acid
Synonyms
cis-4-Fluoro-L-Pro-OH; cis-4-Fluoro-L-proline; (2S,4S)-4-fluoropyrrolidine-2-carboxylic acid; cis-4-Fluoroproline; (4S)-4-fluoro-L-proline; cis 4 Fluoro L Pro OH
Appearance
White to pale yellow solid
Purity
≥ 97% (NMR)
Density
1.300±0.10 g/cm3 (Predicted)
Boiling Point
265.1±40.0 °C (Predicted)
Storage
Store at 2-8 °C
InChI
InChI=1S/C5H8FNO2/c6-3-1-4(5(8)9)7-2-3/h3-4,7H,1-2H2,(H,8,9)/t3-,4-/m0/s1
InChI Key
ZIWHMENIDGOELV-IMJSIDKUSA-N
Canonical SMILES
C1C(CNC1C(=O)O)F
1.An efficient method for high-purity anthocyanin isomers isolation from wild blueberries and their radical scavenging activity.
Chorfa N1, Savard S2, Belkacemi K3. Food Chem. 2016 Apr 15;197 Pt B:1226-34. doi: 10.1016/j.foodchem.2015.11.076. Epub 2015 Nov 21.
An efficient process for the purification of anthocyanin monomeric isomers from wild blueberries of Lake Saint-Jean region (Quebec, Canada) was developed and easy scalable at industrial purpose. The blueberries were soaked in acidified ethanol, filtered, and the filtrate was cleaned by solid phase extraction using silica gel C-18 and DSC-SCX cation-exchange resin. Anthocyanin-enriched elutes (87 wt.%) were successfully fractionated by preparative liquid chromatography. The major anthocyanins mono-galactoside, -glucoside and -arabinoside isomers of delphinidin, cyanidin, petunidin, peonidin and malvidin were isolated with a purity up to 100% according to their LC-MS and (1)H NMR spectra. The oxygen radical absorbance capacity (ORAC) of the obtained pure anthocyanins was evaluated. Delphinidin-3-galactoside has the highest capacity (13.062 ± 2.729 μmol TE/μmol), and malvidin-3-glucoside the lowest (0.851 ± 0.032 μmol TE/μmol). A mechanistic pathway preview is suggested for the anthocyanins scavenging free radical activity by hydrogen transfer.
2.Identification of a highly sulfated fucoidan from sea cucumber Pearsonothuria graeffei with well-repeated tetrasaccharides units.
Hu Y1, Li S1, Li J1, Ye X1, Ding T1, Liu D1, Chen J1, Ge Z2, Chen S3. Carbohydr Polym. 2015 Dec 10;134:808-16. doi: 10.1016/j.carbpol.2015.06.088. Epub 2015 Jul 29.
Sea cucumber fucoidan is a major bioactive component of sea cucumber. The structures of fucoidans have significant influences on their biological activities. The present study clarified the delicate structure of a fucoidan from Pearsonothuria graeffei. Fucoidan was obtained after papain digestion and purified by ion chromatography. The carbohydrate sequence of fucoidan was firstly determined by negative-ion electrospray tandem mass spectrometry (ES-MS) with collision-induced dissociation of the oligosaccharide fragments, which were obtained by mild acid hydrolysis, and completed by NMR for assignment of the anomeric conformation. It was unambiguously identified as a tetrasaccharide repeating unit with a backbone of [ → 3Fuc (2S, 4S) α1 → 3Fucα1→ 3Fuc (4S) α1 → 3Fuc#7 × 10#]n. The glycosidic bonds between the non-sulfated and 2,4-O-disulfated fucose residues were selectively cleaved, and highly ordered oligosaccharide fragments with a tetrasaccharide repeating unit were obtained.
3.Effects of 4-hydroxyisoleucine from Fenugreek Seeds on Depression-like Behavior in Socially Isolated Olfactory Bulbectomized Rats.
Kalshetti PB1, Alluri R2, Mohan V3, Thakurdesai PA3. Pharmacogn Mag. 2015 Oct;11(Suppl 3):S388-96. doi: 10.4103/0973-1296.168980.
CONTEXT: Antidepressant-like effects of (2S, 3R, 4S)-4-hydroxyisoleucine (4-HI), a major amino acid from fenugreek seeds, has been reported in the animal model of acute depression.
4.[Chemical constituents from Cinnamomum cassia].
He S, Jiang Y, Tu PF. Zhongguo Zhong Yao Za Zhi. 2015 Sep;40(18):3598-602.
Various column chromatography, such as silica gel, Sephadex LH-20, ODS, and semi-preparative HPLC was used to isolate and purify the chemical constituents from Cinnamomum cassia. The structures were determined on the basis of NMR and MS spectral data analysis, together with the comparison with literature data. Fifteen compounds were isolated from the 85% aqueous ethanol extract of C. cassia, and their structures were identified as (2R, 3R)-5,7,3',4'-tetramethoxyflavan-3-ol( 1), (2R, 3R)-5,7-dimethoxy-3',4'-methylenedioxyflavan-3-ol (2), coumarin (3), cinnamic acid (4), (E)-2-hydroxy-phenylpropionic acid cinnamoyl ester (5), 3, 3', 4, 4'-tetrahydroxy biphenyl (6), methylstictic acid (7), epi-boscialin (8), (1R,2S,3S,4S)-2,3-epoxy-1, 4-dihydroxy-5-methyl-5-cyelohexene (9), 4,5-dihydroxy-3-methyl cyclohex-2-enone (10), cis-4-hydroxymellein (11), and 2-hydroxy-4-methoxyl-cinnamaldehyde (12). Compounds 5-11 were obtained from this genus plants for the first time.
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