Title

Acoustical Spectroscopy of Carbohydrate Aqueous Solutions: Saccharides; Alkyl Glycosides; Cyclodextrins. Part I. Conformer Variations

Journal title

Archives of Acoustics

Yearbook

2010

Volume

vol. 35

Issue

No 4

Authors

Kaatze, Udo

Keywords

acoustical spectroscopy ; non-equilibrium spectroscopy ; carbohydrate solutions

Divisions of PAS

Nauki Techniczne

Coverage

715-738

Publisher

Polish Academy of Sciences, Institute of Fundamental Technological Research, Committee on Acoustics

Date

2010

Type

Artykuły / Articles

Identifier

DOI: 10.2478/v10168-010-0054-9

Source

Archives of Acoustics; 2010; vol. 35; No 4; 715-738

References

Akashi N. (2000), Measurements of acoustic properties of aqueous dextran solutions in the VHF/UHF range, Ultrasonics, 38, 915. ; Angyal S. (1984), The composition of reducing sugars, [in:] Advances in carbohydrate chemistry and biochemistry, R. S. Tipson, and D. Horton [Eds.], Academic, New York, 42, 15. ; Aoudia M. (1998), Aggregation behavior of sugar surfactants in aqueous solutions: effects of temperature and addition of nonionic polymers, J. Colloid Interface Sci, 206, 158. ; Bae J.-R. (2009), Low-frequency ultrasonic relaxation of β-cyclodextrin and adenosine 5'-monophosphate in aqueous solution, Bull. Korean Chem. Soc, 30, 145. ; Balcerzak A. (2002), Absorption of ultrasonic waves in aqueous binary mixtures of α -cyclodextrin and some amphiphilic substances, Mol. Quantum Acoust, 23, 15. ; Balcerzak A. (2008), Ultrasonic measurements of aqueous solutions of β-cyclodextrin with alkyl pyridinium bromides, Arch. Acoust, 34, 345. ; Behrends R. (2004), Ultrasonic and dielectric study of nonequilibrium monosaccharide solutions in water, Biophys. Chem, 111, 89. ; Bertozzi C. (2001), Chemical glycobiology, Science, 291, 2357. ; Best R. (2001), Molecular dynamics and NMR study of the α(1 → 4) and α(1 → 6) glycosidic linkages: maltose and isomaltose, J. Phys. Chem. B, 105, 4742. ; Bhattia A. (1967), Ultrasonic Absorption. ; Dove A. (2001), The bittersweet promise of glycobiology, Nature Biotechnol, 19, 913. ; Eggers F. (1996), Broad-band ultrasonic measurement techniques for liquids, Meas. Sci. Technol, 7, 1. ; Eggers F. (1994), New ultrasonic resonator cells for absorption and velocity measurements in liquids below 1 MHz, Meas. Sci. Technol, 5, 1131. ; (2000), Carbohydrates in Chemistry and Biology, 1-4. ; Flood A. (1996), Mutarotation of D-fructose in aqueous - ethanolic solutions and its influence on crystallisation, Carbohydr. Res, 288, 45. ; Fukada K. (2000), Stereochemical aspects of micellar properties of esterified glucoside surfactants in water: apparent molar volume, adiabatic compressibility, and aggregation number, Colloid Polym. Sci, 278, 576. ; Fukahori T. (2006), Dynamic study of interaction between β-cyclodextrin and aspirin by the ultrasonic relaxation method, J. Phys. Chem. B, 110, 4487. ; Fukahori T. (2004a), Kinetics on isomeric alcohols recognition by α- and β-cyclodextrins using ultrasonic relaxation method, Bull. Chem. Soc. Japan, 77, 2193. ; Fukahori T. (2004b), Ultrasonic relaxation due to inclusion complex of amino acid by β-cyclodextrin in aqueous solution, J. Acoust. Soc. Am, 115, 2325. ; Gabius H.-J. (2000), Biological information transfer beyond the genetic code: the sugar code, Naturwissenschaften, 87, 108. ; Gabius H.-J. (2004), Chemical biology of the sugar code, ChemBioChem, 5, 740. ; Galema S. A. (1992), <i>The effect of stereochemistry on carbohydrate hydration in aqueous solutions</i>, Dissertation, Rijksuniversiteit Groningen. ; Glasstone S. (1941), The theory of rate processes. ; Hagen R. (2004), Conformational kinetics of disaccharides in aqueous solutions, J. Chem. Phys, 120, 9656. ; Hajduk P. (1993), Picosecond dynamics of simple monosaccharides as probed by nmr and molecular dynamics simulations, J. Am. Chem. Soc, 115, 9196. ; Haller J. (2008a), Kinetics of conformer formation of glucose and maltose in aqueous solutions, Chem. Phys. Lett, 463, 413. ; Haller J. (2008b), Complexation versus micelle formation: α-cyclodextrin + n-decyltrimethylammonium bromide aqueous solutions, Chem. Phys. Lett, 463, 94. ; Haller J. (2009a), Monomer exchange and rotational isomerization of alkyl monoglycosides in water, J. Phys. Chem. B, 113, 12283. ; Haller J. (2009b), Ultrasonic spectrometry of aqueous solutions of alkyl maltosides: kinetics of micelle formation and head group isomerization, Chem. Phys. Chem, 10, 2703. ; Haller J. (2009c), Octylglucopyranoside and cyclodextrin in water: self-aggregation and complex formation, J. Phys. Chem B, 113, 1940. ; Haller J. (2006), Ultrasonic attenuation spectrometry study of α-cyclodextrin + KI complexation in water, Chem. Phys. Lett, 429, 97. ; Hasted J. (1973), Aqueous Dielectrics. ; Hazekamp A. (2006), Structure elucidation of the tetrahydrocannabinol complex with randomly methylated β-cyclodextrin, Eur. J. Pharmaceut. Sci, 29, 340. ; Hill K. (1997), Alkyl polyglycosides: technology, properties and applications. ; Hurtley S. (2001), Cinderella's coach is ready, Science, 291, 2337. ; Jutunen J. (2005), In-vitro corneal permeation of cannabinoids and their water-soluble phosphate ester, J. Pharm. Pharmacol, 57, 1153. ; Kaatze F. (2008), Ultrasonic velocity measurements in liquids with high resolution - techniques, selected applications and perspectives, Meas. Sci. Technol, 19, doi.org/10.1088/0957-0233/19/6/062001 ; Kaatze U. (1993), Ultrasonic spectroscopy of liquids. Extending the frequency range of variable sample length pulse technique, Meas. Sci. Technol, 4, 1257. ; Kaatze U. (1996), Variable pathlength cells for precise hypersonic spectrometry of liquids up to 5 GHz, Ultrasonics, 34, 51. ; Kaatze U. (1988), Acoustical absorption spectroscopy of liquids between 0.15 and 3000 MHz: II. Ultrasonic pulse transmission methods, J. Phys. E: Sci. Instrum, 21, 98. ; Kirschner K. (2001), Solvent interactions determine carbohydrate conformation, Proc. Natl. Acad. Sci. USA, 98, 10541. ; Kogelberg H. (2003), New structural insights into carbohydrate-protein interactions from NMR spectroscopy, Curr. Opin. Struct. Biol, 13, 646. ; Kuttel M. (2005), Free energy surfaces for the α(1→4)-glycosidic linkage: implications for polysaccharide solution structure and dynamics, J. Phys. Chem. B, 109, 7468. ; Lehmann J. (1996), Carbohydrates. ; Lindhorst T. (2000), Essentials of Carbohydrate Chemistry and Biochemistry. ; López O. (2001), Influence of the hydrophobic tail of alkyl glucosides on their ability to solubilize stratum corneum lipid liposomes, Colloid Polym. Sci, 279, 909. ; Maeder T. (2002), Sweet medicines, Sci. Am, 287, 24, doi.org/10.1038/scientificamerican0702-40 ; Nishida Y. (1984), ¹H-NMR studies of (6R)- and (6S)-deuterated D-hexoses: assignment of the preferred rotamers about C5-C6 bond of D-glucose and D-galactose derivatives in solutions, Tetrahedron Lett, 25, 1575. ; Nishikawa S. (2006), Kinetic study for the inclusion complex of carboxylic acids with cyclodextrin by the ultrasonic relaxation method, J. Phys. Chem. B, 110, 26143. ; Ott K.-H. (1996), Molecular dynamics simulations of maltose in water, Carbohydr. Res, 281, 11. ; A. Panneer Selvam (2008), Ultrasonic studies on Lamivudine: β-cyclodextrin and polymer inclusion complexes, Pak. J. Biol. Sci, 11, 656. ; Piercy J. (1961), Ultrasonic relaxation and axial-equatorial isomerization in methyl cyclohexane, J. Acoust. Soc. Am, 33, 198. ; Pillion D. (2002), Synthetic long-chain alkyl maltosides and alkyl sucrose esters as enhancers of nasal insulin absorption, J. Pharm. Sci, 91, 1456. ; Polacek R. (2001), Chair-chair conformational flexibility of monosaccharides linked to the anomer equilibrium, J. Phys. Chem. B, 105, 2894. ; Polacek R. (2001a), A small volume spherical resonator method for the acoustical spectrometry of liquids down to audio frequencies, Meas. Sci. Technol, 12, 1, doi.org/10.1088/0957-0233/12/8/349 ; Polacek R. (2001b), Chair-chair ring inversion in D-fructose coupled to the mutarotation in aqueous-ethanolic solutions, Chem. Phys. Lett, 345, 93. ; Polacek R. (2003), A high-Q easy-to-handle biconcave resonator for acoustic spectrometry of liquids, Meas. Sci. Technol, 14, 1068. ; Polacek R. (2002), Chair-chair conformational flexibility, pseudorotation, and exocyclic group isomerization of monosaccharides in water, J. Chem. Phys, 116, 2973. ; Reinsborough V. (2004), Inclusion complexation involving sugar-containing species: β-cyclodextrin and sugar surfactants, Can. J. Chem.-Rev. Can. Chimie, 82, 45. ; W. von Rybinski (1998), Alkyl polyglycosides - properties and applications of a new class of surfactants, Angew. Chem. Int. Ed. Engl, 37, 1328. ; Schnupf U. (2007), DTF studies of the disaccharide α-maltose: relaxed isopotential maps, Carbohydrate Res, 342, 2270. ; Sears P. (1999), Carbohydrate mimetics: a new strategy for tackling the problem of carbohydrate-mediated biological recognition, Angew. Chem. Int. Ed. Engl, 38, 2300. ; Sears P. (2001), Toward automated synthesis of oligosaccharides and glycoproteins, Science, 291, 2344. ; Shirota K. (2001), Characterization of novel kidney-specific delivery system using alkylgucoside vector, J. Pharmacol. Exp. Ther, 299, 459. ; Snyder J. (1986), D-idose: a one- and two-dimensional NMR investigation of solution composition and conformation, J. Org. Chem, 51, 2694. ; Stenger J. (2000), Molecular dynamics and kinetics of monosaccharides in solution. A broadband ultrasonic relaxation study, J. Phys. Chem. B, 104, 4782. ; Tvaroška I. (1989), Anomeric and exo-anomeric effects in carbohydrate chemistry, Adv. Carbohydrate Chem. Biochem, 47, 45. ; Valente A. (2005), Interactions between n-octyl and nnonyl β-D-glucosides and α- and β-cyclodextrins as seen by self-diffusion NMR, J. Colloid Interface Sci, 281, 218. ; Yamaguchi K. (2005), Dynamic interaction between alkylammonium ions and β-cyclodextrin by means of ultrasonic relaxation, J. Phys. Chem. A, 109, 40.