(-)-(1R,3S)-3-[(t-Butoxycarbonyl)amino]cyclopentanecarboxylic acid - CAS 161660-94-2

Category
BOC-Amino Acids
Catalog number
BAT-003014
CAS number
161660-94-2
Molecular Formula
C11H19NO4
Molecular Weight
229.28
(-)-(1R,3S)-3-[(t-Butoxycarbonyl)amino]cyclopentanecarboxylic acid
Synonyms
Boc-cis-NH(3)cPen-OH; (1S,3R)-N-BOC-1-Aminocyclopentane-3-carboxylic acid; (+)-(1S,3R)-N-BOC-3-AMINOCYCLOPENTANECARBOXYLIC ACID; (1R,3S)-3-((tert-Butoxycarbonyl)amino)cyclopentanecarboxylic acid; (1R,3S)-(-)-3-(Boc-amino)cyclopentanecarboxylic acid; (-)-(1R,3S)-N-Boc-β-homocycloleucine
Appearance
White solid
Purity
≥ 95% (HPLC)
Density
1.150 g/cm3
Melting Point
96.1 °C
Boiling Point
382.5 °C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C11H19NO4/c1-11(2,3)16-10(15)12-8-5-4-7(6-8)9(13)14/h7-8H,4-6H2,1-3H3,(H,12,15)(H,13,14)/t7-,8+/m1/s1
InChI Key
RNJQBGXOSAQQDG-SFYZADRCSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC1CCC(C1)C(=O)O
1.Induced folding of protein-sized foldameric β-sandwich models with core β-amino acid residues.
Olajos G1, Hetényi A, Wéber E, Németh LJ, Szakonyi Z, Fülöp F, Martinek TA. Chemistry. 2015 Apr 13;21(16):6173-80. doi: 10.1002/chem.201405581. Epub 2015 Feb 12.
The mimicry of protein-sized β-sheet structures with unnatural peptidic sequences (foldamers) is a considerable challenge. In this work, the de novo designed betabellin-14 β-sheet has been used as a template, and α→β residue mutations were carried out in the hydrophobic core (positions 12 and 19). β-Residues with diverse structural properties were utilized: Homologous β(3) -amino acids, (1R,2S)-2-aminocyclopentanecarboxylic acid (ACPC), (1R,2S)-2-aminocyclohexanecarboxylic acid (ACHC), (1R,2S)-2-aminocyclohex-3-enecarboxylic acid (ACEC), and (1S,2S,3R,5S)-2-amino-6,6-dimethylbicyclo[3.1.1]heptane-3-carboxylic acid (ABHC). Six α/β-peptidic chains were constructed in both monomeric and disulfide-linked dimeric forms. Structural studies based on circular dichroism spectroscopy, the analysis of NMR chemical shifts, and molecular dynamics simulations revealed that dimerization induced β-sheet formation in the 64-residue foldameric systems. Core replacement with (1R,2S)-ACHC was found to be unique among the β-amino acid building blocks studied because it was simultaneously able to maintain the interstrand hydrogen-bonding network and to fit sterically into the hydrophobic interior of the β-sandwich.
2.Parallel Inhibition of Dopamine Amacrine Cells and Intrinsically Photosensitive Retinal Ganglion Cells in a Non-Image-Forming Visual Circuit of the Mouse Retina.
Vuong HE1, Hardi CN2, Barnes S3, Brecha NC4. J Neurosci. 2015 Dec 2;35(48):15955-70. doi: 10.1523/JNEUROSCI.3382-15.2015.
An inner retinal microcircuit composed of dopamine (DA)-containing amacrine cells and melanopsin-containing, intrinsically photosensitive retinal ganglion cells (M1 ipRGCs) process information about the duration and intensity of light exposures, mediating light adaptation, circadian entrainment, pupillary reflexes, and other aspects of non-image-forming vision. The neural interaction is reciprocal: M1 ipRGCs excite DA amacrine cells, and these, in turn, feed inhibition back onto M1 ipRGCs. We found that the neuropeptide somatostatin [somatotropin release inhibiting factor (SRIF)] also inhibits the intrinsic light response of M1 ipRGCs and postulated that, to tune the bidirectional interaction of M1 ipRGCs and DA amacrine cells, SRIF amacrine cells would provide inhibitory modulation to both cell types. SRIF amacrine cells, DA amacrine cells, and M1 ipRGCs form numerous contacts. DA amacrine cells and M1 ipRGCs express the SRIF receptor subtypes sst(2A) and sst4 respectively.
3.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.
4.Discovery of D1 Dopamine Receptor Positive Allosteric Modulators: Characterization of Pharmacology and Identification of Residues that Regulate Species Selectivity.
Lewis MA1, Hunihan L1, Watson J1, Gentles RG1, Hu S1, Huang Y1, Bronson J1, Macor JE1, Beno BR1, Ferrante M1, Hendricson A1, Knox RJ1, Molski TF1, Kong Y1, Cvijic ME1, Rockwell KL1, Weed MR1, Cacace AM1, Westphal RS1, Alt A1, Brown JM2. J Pharmacol Exp Ther. 2015 Sep;354(3):340-9. doi: 10.1124/jpet.115.224071. Epub 2015 Jun 24.
The present studies represent the first published report of a dopamine D1 positive allosteric modulator (PAM). D1 receptors have been proposed as a therapeutic target for the treatment of cognitive deficits associated with schizophrenia. However, the clinical utility of orthosteric agonist compounds is limited by cardiovascular side effects, poor pharmacokinetics, lack of D1 selectivity, and an inverted dose response. A number of these challenges may be overcome by utilization of a selective D1 PAM. The current studies describe two chemically distinct D1 PAMs: Compound A [1-((rel-1S,3R,6R)-6-(benzo[d][1,3]dioxol-5-yl)bicyclo[4.1.0]heptan-3-yl)-4-(2-bromo-5-chlorobenzyl)piperazine] and Compound B [rel-(9R,10R,12S)-N-(2,6-dichloro-3-methylphenyl)-12-methyl-9,10-dihydro-9,10-ethanoanthracene-12-carboxamide]. Compound A shows pure PAM activity, with an EC50 of 230 nM and agonist activity at the D2 receptor in D2-expressing human embryonic kidney cells.
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