Boc-O-benzyl-L-trans-4-hydroxyproline
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Boc-O-benzyl-L-trans-4-hydroxyproline

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Category
BOC-Amino Acids
Catalog number
BAT-007147
CAS number
54631-81-1
Molecular Formula
C17H23NO5
Molecular Weight
321.38
Boc-O-benzyl-L-trans-4-hydroxyproline
IUPAC Name
(2S,4R)-1-[(2-methylpropan-2-yl)oxycarbonyl]-4-phenylmethoxypyrrolidine-2-carboxylic acid
Synonyms
Boc-L-Hyp(Bzl)-OH
Appearance
White to off-white powder
Purity
≥ 98% (HPLC)
Density
1.22 g/cm3
Melting Point
64-76 °C
Boiling Point
461.342°C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C17H23NO5/c1-17(2,3)23-16(21)18-10-13(9-14(18)15(19)20)22-11-12-7-5-4-6-8-12/h4-8,13-14H,9-11H2,1-3H3,(H,19,20)/t13-,14+/m1/s1
InChI Key
DGIGGVANZFKXLS-KGLIPLIRSA-N
Canonical SMILES
CC(C)(C)OC(=O)N1CC(CC1C(=O)O)OCC2=CC=CC=C2
1.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.
2.Stability of dicyclohexylamine and fumagillin in honey.
van den Heever JP1, Thompson TS2, Curtis JM3, Pernal SF4. Food Chem. 2015 Jul 15;179:152-8. doi: 10.1016/j.foodchem.2015.01.111. Epub 2015 Jan 31.
Fumagillin is extensively used to control nosema disease in apiculture. In the commercial formulation, fumagillin is present as a salt in an equimolar quantity with dicyclohexylamine (DCH). In this study DCH was observed to be significantly more resistant to degradation in honey than fumagillin using LC-MS/MS analysis. Observed half-lives for DCH ranged from a minimum of 368 days when kept at 34 °C in darkness, to a maximum of 852 days when stored at 21 °C in darkness. A maximum half-life of 246 days was observed for fumagillin in samples kept in darkness at a temperature of 21 °C. The observed half-life of fumagillin was estimated to be 3 days when exposed to light at 21 °C, and complete decomposition was observed after 30 days under the same conditions. The stability of DCH, combined with its genotoxicity and tumorigenic properties make it an important potential contaminant in honey destined for human consumption.
3.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.
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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