Solubilities of Glycine and Its Oligopeptides in Aqueous SolutionsClick to copy article linkArticle link copied!
Abstract
The solubilities at 298.15 K of glycine and its oligopeptides (glycylglycine, triglycine, tetraglycine, pentaglycine, and hexaglycine) in aqueous solution at various pH values and concentrations of NaCl, PEG 6000, and ethanol are reported. At high and low pH, the solubilities increase remarkably. The solubilities generally decrease with an increase of the concentrations of ethanol and PEG 6000 in the experimental range, which indicates that ethanol and PEG 6000 can be used as an antisolvent or precipitant for the precipitation and crystallization of glycine and its oligopeptides. As the NaCl concentration increases, the solubility of glycine first decreases and then increases, while the solubilities of glycylglycine and triglycine increase monotonically with the NaCl concentration.
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(25)
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(12)
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(12)
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(8)
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(10)
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(13)
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(3)
, 488-497. https://doi.org/10.1021/acs.jced.7b00486
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(10)
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(1)
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(2)
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(5)
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(5)
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(9)
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(2)
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(6)
, 1787-1792. https://doi.org/10.1021/je800713c
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(5)
, 1133-1137. https://doi.org/10.1021/je7006988
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(3)
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(12)
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(10)
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(7)
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(12)
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https://doi.org/10.1098/rsos.230942
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(7)
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(4)
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(1)
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(7)
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(8)
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(8)
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(12)
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(2)
, 264-279. https://doi.org/10.1007/s10953-015-0314-4
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dl
-serine and
dl
-phenylalanine in aqueous mixtures of dimethyl sulfoxide and solvation thermodynamics. RSC Advances 2015, 5
(85)
, 69839-69847. https://doi.org/10.1039/C5RA12403D
- Gianmario Martra, Chiara Deiana, Yuriy Sakhno, Ilvis Barberis, Marco Fabbiani, Marco Pazzi, Marco Vincenti. The Formation and Self‐Assembly of Long Prebiotic Oligomers Produced by the Condensation of Unactivated Amino Acids on Oxide Surfaces. Angewandte Chemie 2014, 126
(18)
, 4759-4762. https://doi.org/10.1002/ange.201311089
- Gianmario Martra, Chiara Deiana, Yuriy Sakhno, Ilvis Barberis, Marco Fabbiani, Marco Pazzi, Marco Vincenti. The Formation and Self‐Assembly of Long Prebiotic Oligomers Produced by the Condensation of Unactivated Amino Acids on Oxide Surfaces. Angewandte Chemie International Edition 2014, 53
(18)
, 4671-4674. https://doi.org/10.1002/anie.201311089
- Aaron J. Smith, Farukh I. Ali, Dmitriy V. Soldatov. Glycine homopeptides: the effect of the chain length on the crystal structure and solid state reactivity. CrystEngComm 2014, 16
(31)
, 7196-7208. https://doi.org/10.1039/C4CE00630E
- Anna Akinshina, Etienne Jambon-Puillet, Patrick B Warren, Massimo G Noro. Self-consistent field theory for the interactions between keratin intermediate filaments. BMC Biophysics 2013, 6
(1)
https://doi.org/10.1186/2046-1682-6-12
- Luís Fernando Mercier Franco, Silvana Mattedi, Pedro de Alcântara Pessôa Filho. A new approach for the thermodynamic modeling of the solubility of amino acids and β-lactam compounds as a function of pH. Fluid Phase Equilibria 2013, 354 , 38-46. https://doi.org/10.1016/j.fluid.2013.06.009
- Monir Hosseini Anvari, Gholamreza Pazuki, Saeed Seyfi Kakhki, Babak Bonakdarpour. Application of the SAFT-VR equation of state in estimation of physiochemical properties of amino acid solutions. Journal of Molecular Liquids 2013, 184 , 24-32. https://doi.org/10.1016/j.molliq.2013.04.024
- Mariana Ornelas, Dianne Loureiro, Maria João Araújo, Eduardo Marques, Cristina Dias-Cabral, Manuel Azenha, Fernando Silva. Synthesis of glycylglycine-imprinted silica microspheres through different water-in-oil emulsion techniques. Journal of Chromatography A 2013, 1297 , 138-145. https://doi.org/10.1016/j.chroma.2013.04.077
- Vijay M. Krishnamurthy, Venkata S. Raman, Richard A. Mowery, Michelle Hentz, James D. Baleja, Bryan F. Shaw, Krishna Kumar, . Ligand-Induced Protein Mobility in Complexes of Carbonic Anhydrase II and Benzenesulfonamides with Oligoglycine Chains. PLoS ONE 2013, 8
(3)
, e57629. https://doi.org/10.1371/journal.pone.0057629
- S. Frølund, M.K. Nøhr, R. Holm, B. Brodin, C.U. Nielsen. Potential involvement of the proton-coupled amino acid transporter PAT1 (SLC36A1) in the delivery of pharmaceutical agents. Journal of Drug Delivery Science and Technology 2013, 23
(4)
, 293-306. https://doi.org/10.1016/S1773-2247(13)50046-3
- Atsushi Hirano, Kentaro Shiraki, Tsutomu Arakawa. Polyethylene glycol behaves like weak organic solvent. Biopolymers 2012, 97
(2)
, 117-122. https://doi.org/10.1002/bip.21708
- Ali Daneshfar, Masoomeh Baghlani, Reza Sadeghi Sarabi, Reza Sahraei, Shahriyar Abassi, Haydar Kaviyan, Tahereh Khezeli. Solubility of citric, malonic, and malic acids in different solvents from 303.2 to 333.2K. Fluid Phase Equilibria 2012, 313 , 11-15. https://doi.org/10.1016/j.fluid.2011.09.033
- Jie LU, Zhen LI, Xiaolin JIANG, Sohrab ROHANI. Solubility of L-Phenylalanine in Aqueous Solutions. JOURNAL OF CHEMICAL ENGINEERING OF JAPAN 2010, 43
(9)
, 810-813. https://doi.org/10.1252/jcej.10we013
- Zhenning Yan, Xiaoge Wang, Ronghua Xing, Jianji Wang. Volumetric and conductometric studies on the interactions of dipeptides with sodium acetate and sodium butyrate in aqueous solutions at T=298.15K. The Journal of Chemical Thermodynamics 2009, 41
(12)
, 1343-1349. https://doi.org/10.1016/j.jct.2009.06.010
- . Solubility Data in Binary Solvent Mixtures. 2009, 203-505. https://doi.org/10.1201/9781439804889-c3
- T.S. Banipal, Damanjit Kaur, P.K. Banipal, Gagandeep Singh. Interactions of some peptides with sodium acetate and magnesium acetate in aqueous solutions at 298.15 K: A volumetric approach. Journal of Molecular Liquids 2008, 140
(1-3)
, 54-60. https://doi.org/10.1016/j.molliq.2008.01.004
- Xia Yang, Jie Lu, Xiu-Juan Wang, Chi-Bun Ching. Effect of sodium chloride on the nucleation and polymorphic transformation of glycine. Journal of Crystal Growth 2008, 310
(3)
, 604-611. https://doi.org/10.1016/j.jcrysgro.2007.11.072
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