N-α-Allyloxycarbonylglycine dicyclohexylammonium salt
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N-α-Allyloxycarbonylglycine dicyclohexylammonium salt

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Category
Other Unnatural Amino Acids
Catalog number
BAT-005947
CAS number
110637-40-6
Molecular Formula
C18H32N2O4
Molecular Weight
340.46
N-α-Allyloxycarbonylglycine dicyclohexylammonium salt
IUPAC Name
N-cyclohexylcyclohexanamine;2-(prop-2-enoxycarbonylamino)acetic acid
Synonyms
Aloc-Gly-OH DCHA; Alloc-Gly-OH DCHA
Related CAS
90711-56-1 (free acid)
Purity
95%
InChI
InChI=1S/C12H23N.C6H9NO4/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12;1-2-3-11-6(10)7-4-5(8)9/h11-13H,1-10H2;2H,1,3-4H2,(H,7,10)(H,8,9)
InChI Key
VVGNWCIOTXQIKJ-UHFFFAOYSA-N
Canonical SMILES
C=CCOC(=O)NCC(=O)O.C1CCC(CC1)NC2CCCCC2
1.Spectrophotometric and chromatographic determination of insensitive energetic materials: HNS and NTO, in the presence of sensitive nitro-explosives.
Can Z1, Uzer A, Tekdemir Y, Erçağ E, Türker L, Apak R. Talanta. 2012 Feb 15;90:69-76. doi: 10.1016/j.talanta.2011.12.077. Epub 2012 Jan 4.
As there are no molecular spectroscopic determination methods for the most widely used insensitive energetic materials, 2,2',4,4',6,6'-hexanitrostilbene (HNS) and 3-nitro-1,2,4-triazole-5-one (NTO), in the presence of sensitive nitro-explosives, two novel spectrophotometric methods were developed. For HNS and TNT mixtures, both analytes react with dicyclohexylamine (DCHA) forming different colored charge-transfer complexes, which can be resolved by derivative spectroscopy. The spectrophotometric method for NTO measures the 416-nm absorbance of its yellow-colored Na(+)NTO(-) salt formed with NaOH. TNT, if present, is pre-extracted into IBMK as its Meisenheimer anion forming an ion-pair with the cationic surfactant cetyl pyridinium (CP(+)) in alkaline medium, whereas the unextracted NTO is determined in the aqueous phase. The molar absorptivity (ε, L mol(-1)cm(-1)) and limit of quantification (LOQ, mg L(-1)) are as follows: for HNS, ε=2.75 × 10(4) and LOQ=0.
2.Silicon-mediated changes in polyamines participate in silicon-induced salt tolerance in Sorghum bicolor L.
Yin L1,2,3, Wang S1,2, Tanaka K3, Fujihara S4, Itai A3, Den X1,2, Zhang S1,2. Plant Cell Environ. 2016 Feb;39(2):245-58. doi: 10.1111/pce.12521. Epub 2015 Apr 17.
Silicon (Si) is generally considered a beneficial element for the growth of higher plants, especially under stress conditions, but the mechanisms remain unclear. Here, we tested the hypothesis that Si improves salt tolerance through mediating important metabolism processes rather than acting as a mere mechanical barrier. Seedlings of sorghum (Sorghum bicolor L.) growing in hydroponic culture were treated with NaCl (100 mm) combined with or without Si (0.83 mm). The result showed that supplemental Si enhanced sorghum salt tolerance by decreasing Na(+) accumulation. Simultaneously, polyamine (PA) levels were increased and ethylene precursor (1-aminocyclopropane-1-carboxylic acid: ACC) concentrations were decreased. Several key PA synthesis genes were up-regulated by Si under salt stress. To further confirm the role of PA in Si-mediated salt tolerance, seedlings were exposed to spermidine (Spd) or a PA synthesis inhibitor (dicyclohexylammonium sulphate, DCHA) combined with salt and Si.
3.Induction of apoptosis in K562 cells by dicyclohexylammonium salt of hyperforin through a mitochondrial-related pathway.
Liu JY1, Liu Z, Wang DM, Li MM, Wang SX, Wang R, Chen JP, Wang YF, Yang DP. Chem Biol Interact. 2011 Apr 25;190(2-3):91-101. doi: 10.1016/j.cbi.2011.02.026. Epub 2011 Mar 3.
Hyperforin is an abundant phloroglucinol-type constituent isolated from the extract of the flowering upper portion of the plant Hypericum perforatum L. The dicyclohexylammonium salt of hyperforin (DCHA-HF) has exhibited antitumor and antiangiogenic activities in various cancer cells. Here, the antitumor effects of DCHA-HF on the chronic myeloid leukemia K562 cell line were investigated for the first time. DCHA-HF exhibited dose- and time-dependent inhibitory activities against K562 cells, with IC(50) values of 8.6 and 3.2 μM for 48 h and 72 h of treatment, respectively, which was more effective than that of the hyperforin. In contrast, little cytotoxic activity was observed with DCHA-HF on HUVECs. DCHA-HF treatment resulted in induction of apoptosis as evidenced from DNA fragmentation, nuclear condensation and increase of early apoptotic cells by DAPI staining analysis, TUNEL assay and Annexin V-FITC/PI double-labeled staining analysis, respectively.
4.Gel sculpture: moldable, load-bearing and self-healing non-polymeric supramolecular gel derived from a simple organic salt.
Sahoo P1, Sankolli R, Lee HY, Raghavan SR, Dastidar P. Chemistry. 2012 Jun 25;18(26):8057-63. doi: 10.1002/chem.201200986. Epub 2012 May 24.
An easy access to a library of simple organic salts derived from tert-butoxycarbonyl (Boc)-protected L-amino acids and two secondary amines (dicyclohexyl- and dibenzyl amine) are synthesized following a supramolecular synthon rationale to generate a new series of low molecular weight gelators (LMWGs). Out of the 12 salts that we prepared, the nitrobenzene gel of dicyclohexylammonium Boc-glycinate (GLY.1) displayed remarkable load-bearing, moldable and self-healing properties. These remarkable properties displayed by GLY.1 and the inability to display such properties by its dibenzylammonium counterpart (GLY.2) were explained using microscopic and rheological data. Single crystal structures of eight salts displayed the presence of a 1D hydrogen-bonded network (HBN) that is believed to be important in gelation. Powder X-ray diffraction in combination with the single crystal X-ray structure of GLY.1 clearly established the presence of a 1D hydrogen-bonded network in the xerogel of the nitrobenzene gel of GLY.
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