(-)-(1R,3S)-3-[(9-Fluorenylmethoxycarbonyl)amino]cyclopentanecarboxylic acid - CAS 220497-67-6

Category
Cyclic Amino Acids
Catalog number
BAT-005345
CAS number
220497-67-6
Molecular Formula
C21H21NO4
Molecular Weight
351.40
(-)-(1R,3S)-3-[(9-Fluorenylmethoxycarbonyl)amino]cyclopentanecarboxylic acid
Synonyms
Fmoc-cis-NH(3)cPen-OH; (-)-(1R,3S)-N-Fmoc-3-aminocyclopentane carboxylic acid; (-)-(1R,3S)-N-Fmoc-β-homocycloleucine; (1R,3S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)cyclopentane-1-carboxylic acid
Appearance
White powder
Purity
≥ 98% (HPLC)
Density
1.320 g/cm3
Melting Point
163.8 °C
Boiling Point
584.8 °C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C21H21NO4/c23-20(24)13-9-10-14(11-13)22-21(25)26-12-19-17-7-3-1-5-15(17)16-6-2-4-8-18(16)19/h1-8,13-14,19H,9-12H2,(H,22,25)(H,23,24)/t13-,14+/m1/s1
InChI Key
BHDMUBZVWRSQOT-KGLIPLIRSA-N
Canonical SMILES
C1CC(CC1C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
1.Neuroprotective potential of the group III mGlu receptor agonist ACPT-I in animal models of ischemic stroke: In vitro and in vivo studies.
Domin H1, Przykaza Ł2, Jantas D3, Kozniewska E4, Boguszewski PM5, Śmiałowska M6. Neuropharmacology. 2016 Mar;102:276-94. doi: 10.1016/j.neuropharm.2015.11.025. Epub 2015 Dec 2.
In the present study, we investigated the effect of ACPT-I [(1S, 3R,4S)-1-aminocyclopentane-1,2,4-tricarboxylic acid], a blood-brain-barrier permeable agonist of group III mGlu receptor, against oxygen-glucose deprivation (OGD)-evoked neuronal cell death in primary neuronal cell cultures and in the model of transient middle cerebral artery occlusion (MCAO) in rats. We found that ACPT-I (1-200 μM) in a concentration- and time-dependent way attenuated the OGD-induced neuronal cell damage, being also effective after a delayed application (30 min after OGD). The neuroprotective effects of ACPT-I were blocked by the group III mGlu receptor antagonist, (RS)-alpha-cyclopropyl-4-phosphonophenyl glycine (CPPG), and by the activator of cAMP-dependent PKA, 8-Bromo-cAMP, but not by an inhibitor of PI-3-K signaling pathway. Moreover, ACPT-I attenuated the OGD-induced calpain activity and glutamate release. In the in vitro study, we also demonstrated the neuroprotective potential of mGluR4 positive allosteric modulators (PAMs), PHCCC (30 μM) and VU0155041 (10 and 30 μM) and synergism in neuroprotective action of low concentrations of ACPT-I and mGluR4 PAMs suggesting an important role of mGluR4 activation in prevention of ischemic neuronal cell death.
2.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.
3.Astrocyte-derived BDNF supports myelin protein synthesis after cuprizone-induced demyelination.
Fulmer CG1, VonDran MW1, Stillman AA2, Huang Y2, Hempstead BL3, Dreyfus CF4. J Neurosci. 2014 Jun 11;34(24):8186-96. doi: 10.1523/JNEUROSCI.4267-13.2014.
It is well established that BDNF may enhance oligodendrocyte differentiation following a demyelinating lesion, however, the endogenous sources of BDNF that may be harnessed to reverse deficits associated with such lesions are poorly defined. Here, we investigate roles of astrocytes in synthesizing and releasing BDNF. These cells are known to express BDNF following injury in vivo. In culture, they increase BDNF synthesis and release in response to glutamate metabotropic stimulation. Following cuprizone-elicited demyelination in mice, astrocytes contain BDNF and increase levels of metabotropic receptors. The metabotropic agonist, trans-(1S,3R)-1-amino-1,3-cyclopentanedicarboxylic acid (ACPD), was therefore injected into the demyelinating lesion. Increases in BDNF, as well as myelin proteins, were observed. Effects of ACPD were eliminated by coinjection of trkB-Fc to locally deplete BDNF and by deletion of astrocyte-derived BDNF. The data indicate that astrocyte-derived BDNF may be a source of trophic support that can be used to reverse deficits elicited following demyelination.
4.Synthesis of quaternary-carbon-containing and functionalized enantiopure pentanecarboxylic acids from biocatalytic desymmetrization of meso-cyclopentane-1,3-dicarboxamides.
Ao YF1, Wang DX, Zhao L, Wang MX. Chem Asian J. 2015 Apr;10(4):938-47. doi: 10.1002/asia.201402913. Epub 2014 Oct 21.
Catalyzed by Rhodococcus erythropolis AJ270, a nitrile hydratase-amidase containing microbial whole-cell catalyst under mild conditions, enantioselective desymmetrizations of meso-cyclopentane-1,3-dicarbonitriles and cyclopentane-1,3-dicarboxamides were studied. Although the nitrile hydratase was found to exhibit high enzymatic activity, but low 1R enantioselectivity toward dinitriles, a number of 2,2-unsymmetrically substituted meso-cyclopentane-1,3-dicarboxamide substrates were converted by the 1S enantioselective amidase into quaternary carbon-bearing enantiopure (1S,2R,3R)-3-carbamoylcyclopentanecarboxylic acids in yields up to 94 %. The application of the method was demonstrated by convenient and practical transformations of the resulting (1S,2R,3R)-2-allyl-3-carbamoylcyclopentanecarboxylic acid derivatives into functionalized cyclopentane-fused δ-lactam and δ-lactone compounds.
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