Glycine benzyloxycarbonylhydrazide trifluoroacetate
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Glycine benzyloxycarbonylhydrazide trifluoroacetate

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Category
CBZ-Amino Acids
Catalog number
BAT-003206
CAS number
19704-03-1
Molecular Formula
C10H13N3O3·C2HO2F3
Molecular Weight
337.30
Glycine benzyloxycarbonylhydrazide trifluoroacetate
IUPAC Name
benzyl N-[(2-aminoacetyl)amino]carbamate;2,2,2-trifluoroacetic acid
Synonyms
Gly-NHNHZ TFA; (Z-Hydrazido)glycine trifluoroacetate salt; Gly-NHNH-Cbz; benzyl N-[(2-aminoacetyl)amino]carbamate,2,2,2-trifluoroacetic acid
Appearance
White powder
Purity
≥ 98% (TLC)
Melting Point
177-181 °C
Storage
Store at RT
InChI
InChI=1S/C10H13N3O3.C2HF3O2/c11-6-9(14)12-13-10(15)16-7-8-4-2-1-3-5-8;3-2(4,5)1(6)7/h1-5H,6-7,11H2,(H,12,14)(H,13,15);(H,6,7)
InChI Key
ZYWUIPUGRJNRCM-UHFFFAOYSA-N
Canonical SMILES
C1=CC=C(C=C1)COC(=O)NNC(=O)CN.C(=O)(C(F)(F)F)O
1. Glycine in 1-butyl-3-methylimidazolium acetate and trifluoroacetate ionic liquids: effect of fluorination and hydrogen bonding
Ajda Podgoršek, Marina Macchiagodena, Fabio Ramondo, Margarida F Costa Gomes, Agílio A H Pádua Chemphyschem. 2012 May 14;13(7):1753-63. doi: 10.1002/cphc.201100779. Epub 2012 Mar 20.
The solvation of glycine in two ionic liquids (ILs), namely, 1-butyl-3-methylimidazolium acetate, [C(1)C(4)Im][OAc], and 1-butyl-3-methylimidazolium trifluoroacetate, [C(1)C(4)Im][TFA], was studied by a combination of experimental and theoretical methods. The solubility of glycine in both ILs was determined at 333.15 K to be (8.1±0.5) and (1.0±0.5) wt % in [C(1)C(4)Im][OAc] and [C(1)C(4)Im][TFA], respectively. By IR spectroscopy it was found that, when dissolved in the ILs, glycine was mainly present in its zwitterionic form. Structural and energetic aspects of the solvation of glycine in the ILs and in mixtures of ILs and water were investigated by ab initio calculations and molecular dynamic simulations. It was observed that the firstly solvation shell around glycine consisted predominantly of acetate or trifluoroacetate anions, which formed hydrogen bonds either with the carboxylic group of neutral glycine or with the protonated ammonium group of the zwitterionic form. When water is present in the solutions, hydrogen bonds between water and the anion prevail. The overall energy of the system was decomposed into its components between pairs of species. It was established that the dominant contribution to the interaction energy between glycine and the IL was due to hydrogen bonds with the anions and the statistics of hydrogen bonds were analysed.
2. Solid-Phase Insertion of N-mercaptoalkylglycine Residues into Peptides
Spyridon Mourtas, Dimitrios Gatos, Kleomenis Barlos Molecules. 2019 Nov 22;24(23):4261. doi: 10.3390/molecules24234261.
N-mercaptoalkylglycine residues were inserted into peptides by reacting N-free amino groups of peptides, which were initially synthesized on 2-chlorotrityl resin (Cltr) using the Fmoc/tBu method, with bromoacetic acid and subsequent nucleophilic replacement of the bromide by reacting with S-4-methoxytrityl- (Mmt)/S-trityl- (Trt) protected aminothiols. The synthesized thiols containing peptide-peptoid hybrids were cleaved from the resin, either protected by treatment with dichloromethane (DCM)/trifluoroethanol (TFE)/acetic acid (AcOH) (7:2:1), or deprotected (fully or partially) by treatment with trifluoroacetic acid (TFA) solution using triethylsilane (TES) as a scavenger.
3. Trifluoroacetate is an allosteric modulator with selective actions at the glycine receptor
Megan E Tipps, Sangeetha V Iyer, S John Mihic Neuropharmacology. 2012 Sep;63(3):368-73. doi: 10.1016/j.neuropharm.2012.04.011. Epub 2012 Apr 24.
Trifluoroacetic acid is a metabolite of the inhaled anesthetics halothane, desflurane and isoflurane as well as a major contaminant in HPLC-purified peptides. Ligand-gated ion channels, including cys-loop receptors such as the glycine receptor, have been the targets of peptide-based drug design and are considered to be likely candidates for mediating the effects of anesthetics in vivo, but the possible secondary contributions of contaminants and metabolites to these effects have not been studied. We used two-electrode voltage-clamp electrophysiology to test glycine, GABA(A) and 5-HT3 receptors expressed in Xenopus oocytes for their sensitivities to sodium trifluoroacetate. Trifluoroacetate (100 μM-3mM) enhanced the currents elicited by low concentrations of glycine applied to α1 homomeric and α1β heteromeric glycine receptors, but it had no effects when co-applied with a maximally-effective glycine concentration. Trifluoroacetate had no effects on α1β2γ2S GABA(A) or 5-HT3A receptors at any GABA or serotonin concentration tested. The results demonstrate that trifluoroacetate acts as an allosteric modulator at the glycine receptor with greater specificity than other known modulators. These results have important implications for both the secondary effects of volatile anesthetics and the presence of contaminating trifluoroacetate in HPLC-purified peptides, which is potentially an important source of experimental variability or error that requires control.
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