Article history:Received 28 September 2013Received in revised form 28 February 2014Accepted 3 March 2014Available online 15 March 2014
Keywords:SaccharideGlycineDensitySpeed of soundTransfer apparent molar volume at infinitedilutionTransfer apparent molar isentropiccompression at infinite dilution
Densities (ρ) and speeds of sound (u) of some saccharides in aqueous glycine solutions (0.000, 0.025, 0.050, and0.100 mol kg−1) have been measured in the concentration range 0.050–0.100 mol kg−1 at 293.15, 298.15,303.15, 308.15, and 313.15 K. Using the ρ and u data, the apparentmolar volumes at infinite dilution (Vφ
o), trans-
fer apparent molar volumes at infinite dilution (ΔtrVφo), partial molar expansion coefficients ∂Vo
lution (κ s,φo ), and transfer apparent molar isentropic compressions at infinite dilution (Δtrκ s,φ
o ) have been calcu-lated. The trends of variations of experimental and computed parameters have been deliberated in terms ofdifferent types of the interactions occurring in the present ternary system.
Saccharides being the important chemicals of living organism are ofconsiderable interest in various aspects of researches and applications.Saccharides help in stabilizing the native confirmation of ubiquitousglobular proteins or reduce the extent of denaturation by other reagents[1–4]. Most of the saccharides located at the cell surface act as receptorsto the viruses, hormones, enzymes, antibodies, etc. [5]. Therefore thereinteraction studies with proteins have been proved very useful forimmunology, medicine and pharmacology. Besides, the interactions ofamino acid with sugar help us in explicating the intramolecular interac-tions between amino acid residues of glycoproteins and the sugar partof the glycoprotein with proteolytic enzymes.
Even if severalmechanisms for the stabilization of proteins by sugarshave been proposed [6], the understanding of themechanism is still in-complete, probably due to the complex nature of their interactions. Thesimplest approach that may help in this regard and requires less com-plexmeasurement techniques is to study sugar–amino acid interactionsin solutions. Literature surveys point out that these interactions can bestudied by different spectroscopic techniques [7–11], chromatographydata [12,13] and computer calculations [14–16]. In addition, recently,researchers have studied the thermodynamic properties of saccharidesin aqueous electrolytic solutions [17–21]. Anyhow, there is relatively
91 177 2830775.Chauhan).
little information available on such properties in aqueous amino acidssolutions [22–24].
In view of the above, and in light of our previous work [25–31] onthermodynamic studies of ternary systems, in this paper we haveexplored the interactions between D (−) ribose, D (+) maltosemonohydrate and D (+) raffinose pentahydrate (saccharides) andglycine (amino acid) in water.
2. Experimental
2.1. Materials
Thedeionizeddistilledwaterwith a conductivity of 1–2×10−7 s cm−1
and pH of 6.8–7.0 (at 298.15 K) was collected from a Millipore-Elixsystem. The specifications of D (−) ribose (monosaccharide), D (+)maltose monohydrate (disaccharide), D (+) raffinose pentahydrate(trisaccharide) and glycine of high purity were provenance from LOBAChemie and Calbiochem, respectively. The saccharides and glycinewere recrystallized twice in distilled water and dried in vacuum oven.After this they were kept in a vacuum desiccator over anhydrous calci-um chloride at room temperature for a minimum of 48 h. The detailsof the chemicals used in the present work are also given in Table 1.
2.2. Methods and procedures
Stock solutions of glycine (0.025, 0.050, and 0.100 mol kg−1) wereprepared in distilled water and were used as solvents for the
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213S. Chauhan, K. Kumar / Journal of Molecular Liquids 194 (2014) 212–226
preparation of different saccharide solutions. These solutions wereprepared by using Shimadzu balance with a precision of ±0.0001 g.Densities and speeds of sound of aqueous saccharide solutions withand without glycine were measured simultaneously using Anton PaarDSA-5000 instrument. The two-in-one instrument is equipped with adensity cell at a pulse–echo speed of sound cell. Both cells are tempera-ture controlled by a built-in Peltier thermostat. The instrument has abuilt-in thermostat to maintain the temperature between 0 and 70 °C.The instrumentwas calibrated at all studied temperatures with distilledwater, dimethylsulfoxide and 1,4-dioxane. The reproducibility indensity and speed of sound measurements were ±0.2 m s−1 and±2 × 10−6 g cm−3, respectively. The densities and speeds of sound ofthese solvents are found to be in good compliance with the literaturevalues as indexed in Table 2.
3. Results and discussion
3.1. Apparent molar volume
Densities and speeds of sound for different saccharides at molalitiesranging from 0.050 to 0.100 mol kg−1 in water and aqueous glycinesolutions (0.025, 0.050, and 0.100 mol kg−1) have been listed inTable 3. The apparent molar volumes, Vφ, have been estimated fromthe equation
Vφ ¼ Mρ− ρ−ρoð Þ
mρρo
� �ð1Þ
wherem is themolality (mol kg−1) of the solution,M is themolarmassof the saccharides (kg mol−1) and ρo and ρ are the densities of thesolvent and solution (kg m−3), respectively. By examining Table 4, theVφ values altered linearlywithmolalities of saccharides at all concentra-tion of glycine and temperatures, thence, apparent molar volumes atinfinite dilution, Vφ
o , have been obtained by least squares fitting ofexperimental data to the equation,
Vφ ¼ Vφo þ Svm ð2Þ
where Sv is the experimental slope. Vφo represents the solute−solvent
interactions and Sv means the solute–solute interactions. This type oflinear alteration in Vφ values is in contrast to our earlier studies ofSDS–saccharide and CTAB–glycine systems [32,33], where Vφ variesnon-linearly before CMC and then becomes almost constant above theCMC. The evaluated Vφ
o and Sv valueswith standard errors are expressedin Table 5. The Vφ
o values of different saccharides in water are found tobe in good compliance with corresponding literature values [17]. A sur-vey of Table 5 suggests that Vφ
o values are positive for all saccharides inall the studied systems indicating strong solute–solvent interactions [34].Further,Vφ
o values in aqueous glycine systems are higher than thosewith-out glycine and increase with the concentration of glycine. This behaviormaybe explained on thebasis of the following types of interactions occur-ring in the ternary saccharide–amino acid–water system [35]:
(1) hydrophilic–ionic interactions between the OH groups ofsaccharide and the zwitterionic center of glycine,
(2) hydrophilic–hydrophilic interactions between OH groups of sac-charide and the OH groups of glycine through the hydrogen bond,
(3) hydrophilic–hydrophobic interactions between OH groups ofsaccharide/glycine and thenon-polar groups of glycine/ saccharideand
Table 3Densities, ρ, and speeds of sound, u, of saccharides in water and aqueous glycine solutions at different temperatures (T/K).
a m is the molality of saccharides.b mGly is the molality of aqueous glycine solution.
215S. Chauhan, K. Kumar / Journal of Molecular Liquids 194 (2014) 212–226
Table 4Apparent molar volumes, Vφ, and apparent molar isentropic compressions, κs,φ, of saccharides in water and aqueous glycine solutions at different temperatures (T/K).
a mGly is the molality of aqueous glycine solution.
219S. Chauhan, K. Kumar / Journal of Molecular Liquids 194 (2014) 212–226
around the hydroxyl groups of saccharides and zwitterions of glycine.With a rise in temperature the electrostricted water molecules fromthe secondary solvation layer are released into the bulk of water, there-by expanding the solution and causing the large Vφ
o values [36]. The Svvalues in all the studied systems are found to be negative (Table 5),suggesting weak solute–solute interactions; however as documentedin literature they are indicative of hydrophobic hydration in the system[34]. Similar types of interactions have also been proclaimed by KeleiZhuo et al. [23], in their study of monosaccharides in aqueous aminoacid solutions at 298.15 K. In our case, the slopes becomemore negativefor di- and tri-saccharides, suggesting an enhancement of the effectwith the complexity of saccharides that may lead to volume andcompressibility reduction. Thus, it can be figured out that both polarand non-polar groups reduce themobility of water molecules in the hy-dration shell, which in turn leads to the volume and compressibilityreduction.
The transfer apparent molar volume at infinite dilution, ΔtrVφo , of
saccharides fromwater to aqueous glycine solutions have been calculatedby using the equation,
ΔtrVoφ ¼ Vφ
o aq:glycineð Þ−Vφo waterð Þ: ð3Þ
From this equation, it is clear that ΔtrVφo values provide information
only regarding the solute–solvent interactions. The ΔtrVφo values have
been summarized in Table 5 and illustrated in Fig. 1(a–c). The positiveΔtrVφ
o values can be rationalized by applying the cosphere model as de-veloped by Friedman and Krishnan [37]. The above said two types of in-teractions (1) and (2) lead to a positive contribution, while interactionsof the types (3) and (4) give a negative contribution towards the ΔtrVφ
o
values. The observed positive ΔtrVφo values specify that hydrophilic–
ionic/hydrophilic–hydrophilic interactions remain preeminent over hy-drophilic–hydrophobic/hydrophobic–hydrophobic interactions [17]. Itis also evident from Fig. 1(a–c) that ΔtrVφ
o values increase with glycineconcentration and with temperature at the same time. On a compara-tive basis, ΔtrVφ
o values follow the order ribose b maltose b raffinose atall concentrations of glycine (Fig. 2) which is well documented in liter-ature [18]. It may be due to the more dominating nature of interactiontypes (1) and (2) which become quite evident with increased concen-tration of glycine and complexity of saccharides as we move frommono- to di- to tri-saccharides. However, ΔtrVφ
o values of saccharidesfollow the reverse order in aqueous borax solutions where monosac-charides form a strong complex with borax [38]. The increase in Δtrφv
o
values with temperature may be due to the rise in Vφo values of saccha-
rides with temperature.Moreover, the positive ΔtrVφ
o values can be connected to the declinein shrinkage volume in aqueous glycine solutions according to Shahidi'sequation [39],
Voφ ¼ Vv:w: þ Vvoid:−Vshrinkage ð4Þ
where Vv.w. is van der Waal's volume, Vvoid is the associated void orempty volume, andVshrinkage is the shrinkage in volume caused bydiffer-ent solute–solvent interactions. If it is assumed that Vv.w and Vvoid havethe same magnitudes in water as well as in aqueous glycine solutions,
than the decrease in Vshrinkage is the only contributor to the positiveΔtrVφ
o values.
3.2. Expansion coefficient and second derivative
The partial molar expansion coefficients ∂Voφ
.∂T
� �pand second de-
rivatives ∂2Voφ
.∂T2
� �phave been determined by fitting the Vφ
o results in
the equation,
Voφ ¼ aþ bT þ cT2 ð5Þ
where a, b, and c are constants whose values are given in Table 6. The∂Vo
φ
.∂T
� �pvalues for different saccharides inwater and aqueous glycine
solutions are positive (Table 6). The variation of expansion coefficients,∂Vo
φ
.∂T
� �pversus temperature (Fig. 3(a–c)) shows that values increase
with temperature except for the raffinose–water system. This showsthat saccharides behave unlike common electrolytes [40], which is inagreement with the results cited in the literature [41]. Further, it is in-dicative of the prominent caging effect exhibited by saccharides [42].
The magnitudes of ∂2Voφ
.∂T2
� �pvalues give important information re-
garding the structure making or breaking behavior of the solute. Hepler
[43], has suggested the equation, ∂Cop;2
.∂T
� �T¼ −T ∂2Vo
φ
.∂T2
� �pto un-
derstand the structuremaking and breaking capacity of a solute in aque-ous solutions. For a structure breaking solute, the left hand side of above
equation should be positive, and hence ∂2Voφ
.∂T2
� �pshould be negative
for structure breaking and positive for structure making solutes. There-
fore, the positive values of ∂2Voφ
.∂T2
� �p(Table 6) except for raffinose in
water suggest that all saccharides behave as structure makers in aque-ous glycine solutions. This type of behavior of saccharides has alsobeen noticed by P. K. Banipal et al. [18].
3.3. Isentropic compressibility
The isentropic compressibility values have been computed by usingthe equation,
κs ¼1
ρu2 ð6Þ
where u is the speed of sound of solution (m s−1), which is a thermody-namic property at a condition of negligible sound absorption.
The isentropic compressibility, κs, values have been listed in Table 7and illustrated in Fig. 4(a–c). Table 7 and Fig. 4(a–c) reveal that, κsvalues decrease linearly with molal concentration of saccharides andtemperature aswell. This diminution shows that the addition of saccha-rides to the solutions increases the hydrophilic–ionic interactions,which pared the cavities in the solution and the system becomes lesscompressible. Though, the temperature effect on isentropic compress-ibility may be due to the thermal fissure of the water structure around
0
2
4
6
8
10
mGly/ mol·kg-1
mGly/ mol·kg-1
mGly/ mol·kg-1
(a)
0
2
4
6
8
10
12
14
16 (b)
0.00 0.02 0.04 0.06 0.08 0.10
0.00 0.02 0.04 0.06 0.08 0.10
0.00 0.02 0.04 0.06 0.08 0.1002468
10121416182022242628303234 (c)
φΔ t
rVo
x106 /
m3 ·
mol
-1φ
Δ trV
o x1
06 / m
3 ·m
ol-1
φΔ t
rVo
x106 /
m3 ·
mol
-1
Fig. 1. ΔtrV φo versus molality of glycine for (a) D (−) ribose, (b) D (+) maltose
monohydrate, and (c) D (+) raffinose pentahydrate. ■, T = 293.15 K; ●, T = 298.15 K;▲, T = 303.15 K;▼, T = 308.15 K; , T = 313.15 K.
0.00 0.02 0.04 0.06 0.08 0.100
2
4
6
8
10
12
14
16
18
20
22
24
mGly/ mol·kg-1
φΔ t
rVo
x106 /
m3 ·
mol
-1
Fig. 2. Comparative plot of ΔtrVφo versus molality of glycine at temperature 298.15 K.■, D
(−) ribose;●, D (+) maltose monohydrate; ▲, D (+) raffinose pentahydrate.
220 S. Chauhan, K. Kumar / Journal of Molecular Liquids 194 (2014) 212–226
the zwitterions of glycine and hydrophilic OH groups of saccharides.However, these results are in contradiction with the results retrievedby Nain et al. [36]. In addition, due to the increase in the number ofthe OH group with the type of saccharides, the κs values decrease inthe following order: ribose N maltose N raffinose at all studied glycineconcentrations as reported in Table 7.
3.4. Apparent molar isentropic compression
The apparent molar isentropic compressions, κs,φ, have been calcu-lated using the relation,
κs;φ ¼ κs−κoð Þmρo
� �þ κsVφ ð7Þ
where κs and κo are the isentropic compressibilities of the solution andsolvent (m2N−1), respectively. The apparentmolar isentropic compres-sions, κs,φ, have been recorded in Table 4. As the κs,φ values vary linearlywith molal concentration of saccharides, the apparent molar isentropiccompressions at infinite dilution, κ s,φ
o , and slopes, Sk, can be obtained byusing the method of linear regression of the following relation,
κs;φ ¼ κos;φ þ Skm ð8Þ
where κ s,φo measures the solute–solvent interactions and Sk affords in-
formation regarding solute–solute interaction. The values of κs,φo and Skat different temperatures and concentrations of glycine along withtheir standard errors have been indexed in Table 5. In literature, to thebest of our knowledge, no compressibility data of these saccharides inaqueous amino acid solutions is available for comparison purposes.The negative κ s,φ
o values (Table 5) showing the presence of strong sol-ute–solvent interactions results in less compressible solutions [35].Table 5 pinpoints that all the κ s,φ
o values rise with temperature, but de-cline with glycine concentration. The increase in κ s,φ
o values with tem-perature may be due to the release of large water molecules from thesecondary solvation layer of zwitterions of glycine into the bulk ofwater, which makes the solutions more compressible [44]. However,the magnitudes of different types of ionic interactions seem to be in di-rect relation with increase in glycine concentration in the systemwhichin turn results in more negative κ s,φ
o values. These results further sub-stantiate the fact that hydrophilic–ionic/hydrophilic–hydrophilic inter-actions exceed hydrophilic–hydrophobic/hydrophilic–hydrophobic
a mGly is the molality of aqueous glycine solution.
221S. Chauhan, K. Kumar / Journal of Molecular Liquids 194 (2014) 212–226
interactions. Relatively, lesser Sk values for all the studied systems sug-gest very weak solute–solute interactions.
The transfer apparentmolar isentropic compressions at infinite dilu-tion, Δtrκ s,φ
o , from water to aqueous glycine solutions were calculatedfrom the following equation:
Δtrκos;φ ¼ κo
s;φ aq:glycineð Þ−κos;φ waterð Þ: ð9Þ
The Δtrκ s,φo values are listed in Table 5 and illustrated in Fig. 5(a–c).
Table 5 shows thatΔtrκ s,φo values are positive, and increasewith temper-
ature, but becomes more negative with greater glycine concentration.All these observations show the predominance of hydrophilic–ionic/hydrophilic–hydrophilic interactions in present systems, which are re-sponsible for the release of a large number of water molecules fromthe secondary solvation layer around the glycine zwitterions into thebulk of water. Such type of behavior has also been reported in literature[35]. Relatively, it can be noticed from Fig. 6, that Δtrκ s,φ
o values of vari-ous saccharides increase systematically with their complexity frommono- to di- to tri-saccharides in all concentrations of glycine. Thismay be credited as a result of increased disruption of the solvationlayers around charged centers as a result of escalation in hydroxylgroups–zwitterions i.e. hydrophilic–ionic interactions. These resultsare in compliance with that of results accessed from partial molar vol-ume studies.
4. Conclusions
The increase inΔtrVφo valueswith intricacy of saccharides and glycine
concentration is due to stronger hydrophilic–ionic interactions betweenOH groups of saccharide and zwitterions of glycine amino acid. Despitethis, the rise in ΔtrVφ
o values with temperature is due to the release ofwater molecules from secondary solvation layer around the zwitterions
into the bulk of water. The positive ∂2Voφ
.∂T2
� �pvalues are argued of
structure making behavior of saccharides in aqueous glycine solutions.Further, the positive Δtrκ s,φ
o values in all the studied systems are indica-tive of stronger solute–solvent interactions. All these observationscollectively show the preeminence of hydrophilic–ionic over hydropho-bic–hydrophobic interactions in the present ternary system.
Acknowledgment
Kuldeep Kumar thanks UGC for the award of UGC-BSR researchfellowship Vide UGC Letter F. No. 7-75/2007 (BSR).
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Fig. 4. κs versus molality of (a) D (−) ribose, (b) D (+) maltose monohydrate, and(c) D (+) raffinose pentahydrate in 0.100 mol kg−1 aqueous glycine solution. ■, T =293.15 K;●, T = 298.15 K; ▲, T = 303.15 K;▼, T = 308.15 K;◄, T = 313.15 K.
0
1
2
3
4
5
mGly/ mol·kg-1
mGly/ mol·kg-1
mGly/ mol·kg-1
(a)
0
1
2
3
4
5
6
(b)
0.00 0.02 0.04 0.06 0.08 0.10
0.00 0.02 0.04 0.06 0.08 0.10
0.00 0.02 0.04 0.06 0.08 0.100
1
2
3
4
5
6
(c)
Δ trκ
ο s,φ
x103 /
m3 ·
mol
-1·T
Pa-1
Δ trκ
ο s,φ
x103 /
m3 ·
mol
-1·T
Pa-1
Δ trκ
ο s,φ
x103 /
m3 ·
mol
-1·T
Pa-1
Fig. 5. Δtrκ s,φo versus molality of glycine for (a) D (−) ribose, (b) D (+) maltose
monohydrate, and (c) D (+) raffinose pentahydrate. ■, T = 293.15 K; ●, T = 298.15 K;▲, T = 303.15 K;▼, T = 308.15 K; , T = 313.15 K.
225S. Chauhan, K. Kumar / Journal of Molecular Liquids 194 (2014) 212–226
Fig. 6. Comparative plot ofΔtrκs,φo versusmolality of glycine at temperature 298.15 K.■, D(−) ribose;●, D (+) maltose monohydrate; ▲, D (+) raffinose pentahydrate.
226 S. Chauhan, K. Kumar / Journal of Molecular Liquids 194 (2014) 212–226
