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Volumn 40, Issue 6, 2005, Pages 765-771

Anomeric distinction and oxonium ion formation in acetylated glycosides

Author keywords

Anomers; Electrospray ionization; Mass spectrometry; Neighboring group participation; Oxocarbenium

Indexed keywords

ACETIC ACID; AMMONIA; CARBOHYDRATES; CATIONIC POLYMERIZATION; ISOMERS; REACTION KINETICS;

EID: 21344465888     PISSN: 10765174     EISSN: None     Source Type: Journal    
DOI: 10.1002/jms.848     Document Type: Article
Times cited : (33)

References (34)
  • 1
    • 0001094662 scopus 로고    scopus 로고
    • Glycobiology: Toward understanding the function of sugars
    • Dwek RA. Glycobiology: toward understanding the function of sugars. Chem. Rev. 1996; 96: 683.
    • (1996) Chem. Rev. , vol.96 , pp. 683
    • Dwek, R.A.1
  • 3
    • 0036019810 scopus 로고    scopus 로고
    • Mechanisms of glycopyranosyl and 5-thioglycopyranosyl transfer reactions in solution
    • Bennet AJ, Kitos TE. Mechanisms of glycopyranosyl and 5-thioglycopyranosyl transfer reactions in solution. J. Chem. Soc., Perkin Trans. 2 2002; 7: 1207.
    • (2002) J. Chem. Soc., Perkin Trans. 2 , vol.7 , pp. 1207
    • Bennet, A.J.1    Kitos, T.E.2
  • 7
    • 0025271979 scopus 로고
    • Determination of linkage position and identification of the reducing end in linear oligosaccharides by negative ion fast atom bombardment mass spectrometry
    • Garozzo D, Giuffrida M, Impallomeni G, Ballistreri A, Montuado G. Determination of linkage position and identification of the reducing end in linear oligosaccharides by negative ion fast atom bombardment mass spectrometry. Anal. Chem. 1990; 62: 279.
    • (1990) Anal. Chem. , vol.62 , pp. 279
    • Garozzo, D.1    Giuffrida, M.2    Impallomeni, G.3    Ballistreri, A.4    Montuado, G.5
  • 8
    • 0026142973 scopus 로고
    • Reaction mechanism and fragment ion structure determination of deprotonated small oligosaccharides, studied by negative ion fast atom bombardment (tandem) mass spectrometry
    • Dallinga JW, Heerma W. Reaction mechanism and fragment ion structure determination of deprotonated small oligosaccharides, studied by negative ion fast atom bombardment (tandem) mass spectrometry. Biol. Mass Spectrom. 1991; 20: 215.
    • (1991) Biol. Mass Spectrom. , vol.20 , pp. 215
    • Dallinga, J.W.1    Heerma, W.2
  • 9
    • 0001051792 scopus 로고
    • Linkage position determination in lithium-cationized disaccharides: Tandem mass spectrometry and semiempirical calculations
    • Hofmeister GE, Zhou Z, Leary JA. Linkage position determination in lithium-cationized disaccharides: tandem mass spectrometry and semiempirical calculations. J. Am. Chem. Soc. 1991; 113: 5964.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 5964
    • Hofmeister, G.E.1    Zhou, Z.2    Leary, J.A.3
  • 10
    • 0028389851 scopus 로고
    • Effects of cations and charge types on the metastable decay rates of oligosaccharides
    • Ngoka LC, Gall JF, Lebrilla CB. Effects of cations and charge types on the metastable decay rates of oligosaccharides. Anal. Chem. 1994; 66: 692.
    • (1994) Anal. Chem. , vol.66 , pp. 692
    • Ngoka, L.C.1    Gall, J.F.2    Lebrilla, C.B.3
  • 11
    • 0001384408 scopus 로고
    • Linkage position in oligosaccharides by fast atom bombardment ionization collision-activated dissociation tandem mass spectrometry and molecular modeling
    • Laine RA, Pamidimukkala KM, French AD, Hall RW, Abbas SA, Jain RK, Matta KL. Linkage position in oligosaccharides by fast atom bombardment ionization collision-activated dissociation tandem mass spectrometry and molecular modeling. J. Am. Chem. Soc. 1988; 110: 6931.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 6931
    • Laine, R.A.1    Pamidimukkala, K.M.2    French, A.D.3    Hall, R.W.4    Abbas, S.A.5    Jain, R.K.6    Matta, K.L.7
  • 12
    • 0036923384 scopus 로고    scopus 로고
    • Direct stereochemical assignment of hexose and pentose residues in flavonoid O-glycosides by fast atom bombardment and electrospray ionization mass spectrometry
    • Cuyckens F, Shahat AA, Pieters L, Claeys M. Direct stereochemical assignment of hexose and pentose residues in flavonoid O-glycosides by fast atom bombardment and electrospray ionization mass spectrometry. J. Mass Spectrom. 2002; 37: 1272.
    • (2002) J. Mass Spectrom. , vol.37 , pp. 1272
    • Cuyckens, F.1    Shahat, A.A.2    Pieters, L.3    Claeys, M.4
  • 13
    • 0030248366 scopus 로고    scopus 로고
    • Differentiation of stereochemistry of glycosidic bond configuration: Tandem mass spectrometry of diastereomeric cobalt-glucosyl-glucose disaccharide complexes
    • Smith G, Leary J. Differentiation of stereochemistry of glycosidic bond configuration: tandem mass spectrometry of diastereomeric cobalt-glucosyl- glucose disaccharide complexes. J. Am. Soc. Mass Spectrom. 1996; 7: 953.
    • (1996) J. Am. Soc. Mass Spectrom. , vol.7 , pp. 953
    • Smith, G.1    Leary, J.2
  • 14
    • 0029155896 scopus 로고
    • Determination of both linkage position and anomeric configuration in underivatized glucopyranosyl disaccharides by electrospray mass spectrometry
    • Mulroney B, Traeger JC, Stone BA. Determination of both linkage position and anomeric configuration in underivatized glucopyranosyl disaccharides by electrospray mass spectrometry. J. Mass Spectrom. 1995; 30: 1277.
    • (1995) J. Mass Spectrom. , vol.30 , pp. 1277
    • Mulroney, B.1    Traeger, J.C.2    Stone, B.A.3
  • 15
    • 0038142790 scopus 로고    scopus 로고
    • Rapid and sensitive differentiation of anomers, linkage, and position isomers of disaccharides using high-field asymmetric waveform ion mobility spectrometry (FAIMS)
    • Gabryelski W, Froese KL. Rapid and sensitive differentiation of anomers, linkage, and position isomers of disaccharides using high-field asymmetric waveform ion mobility spectrometry (FAIMS). J. Am. Soc. Mass Spectrom. 2003; 14: 265.
    • (2003) J. Am. Soc. Mass Spectrom. , vol.14 , pp. 265
    • Gabryelski, W.1    Froese, K.L.2
  • 16
    • 0032518331 scopus 로고    scopus 로고
    • An electrospray-ionization tandem mass spectrometry method for determination of the anomeric configuration of glycosyl 1-phosphate derivatives
    • Wolucka BA, Rush JS, Waechter CJ, Shibaev VN, de Hoffmann E. An electrospray-ionization tandem mass spectrometry method for determination of the anomeric configuration of glycosyl 1-phosphate derivatives. Anal. Biochem. 1998; 255: 244.
    • (1998) Anal. Biochem. , vol.255 , pp. 244
    • Wolucka, B.A.1    Rush, J.S.2    Waechter, C.J.3    Shibaev, V.N.4    De Hoffmann, E.5
  • 17
    • 84987044267 scopus 로고
    • Identification of interglycosidic linkages and sugar constituents in disaccharide subunits of larger glycosides by tandem mass spectrometry
    • Domon B, Müller DR, Richter WJ. Identification of interglycosidic linkages and sugar constituents in disaccharide subunits of larger glycosides by tandem mass spectrometry. Org. Mass Spectrom. 1989; 24: 357.
    • (1989) Org. Mass Spectrom. , vol.24 , pp. 357
    • Domon, B.1    Müller, D.R.2    Richter, W.J.3
  • 18
    • 0345004006 scopus 로고    scopus 로고
    • 1-type sugar ions formed from peracerylated methyl pentosides and methyl 6-deoxyhexosides
    • 1-type sugar ions formed from peracerylated methyl pentosides and methyl 6-deoxyhexosides. J. Mass Spectrom. 1999; 34: 346.
    • (1999) J. Mass Spectrom. , vol.34 , pp. 346
    • Vouros, P.1    Müller, D.R.2    Richter, W.J.3
  • 19
    • 84989040028 scopus 로고
    • Electron-impact and chemical-ionization mass spectra of some tetraacerylated anomeric glycosides
    • Kulkarni PS, Kulkarni SY, Pansare VS. Electron-impact and chemical-ionization mass spectra of some tetraacerylated anomeric glycosides. Org. Mass Spectrom. 1986; 21: 23.
    • (1986) Org. Mass Spectrom. , vol.21 , pp. 23
    • Kulkarni, P.S.1    Kulkarni, S.Y.2    Pansare, V.S.3
  • 21
    • 0037997751 scopus 로고
    • Differences in fragmentation behavior between α- and β-linked derivatized xylobiosides: Explanation in terms of sigma conjugation
    • van der Kerk SM, Blok-Tip L, van der Kerk-van Hoof A, Heerma W, Haverkamp J. Differences in fragmentation behavior between α- and β-linked derivatized xylobiosides: explanation in terms of sigma conjugation. Int. J. Mass Spectrom. 1994; 134: 41.
    • (1994) Int. J. Mass Spectrom. , vol.134 , pp. 41
    • Van Der Kerk, S.M.1    Blok-Tip, L.2    Van Der Kerk-Van Hoof, A.3    Heerma, W.4    Haverkamp, J.5
  • 22
    • 84989114123 scopus 로고
    • Unimolecular and collision-induced dissociation reactions of peracetylated methyl glucopyranoside
    • Guevremont R, Pathak VP, Wright JLC. Unimolecular and collision-induced dissociation reactions of peracetylated methyl glucopyranoside. Org. Mass Spectrom. 1990; 25: 101.
    • (1990) Org. Mass Spectrom. , vol.25 , pp. 101
    • Guevremont, R.1    Pathak, V.P.2    Wright, J.L.C.3
  • 23
    • 0029155896 scopus 로고
    • Determination of both linkage position and anomeric configuration in underivatized glucopyranosyl disaccharides by electrospray mass spectrometry
    • Mulroney B, Traeger JC, Stone BA. Determination of both linkage position and anomeric configuration in underivatized glucopyranosyl disaccharides by electrospray mass spectrometry. J. Mass Spectrom. 1995; 30: 1277.
    • (1995) J. Mass Spectrom. , vol.30 , pp. 1277
    • Mulroney, B.1    Traeger, J.C.2    Stone, B.A.3
  • 24
    • 0034554929 scopus 로고    scopus 로고
    • Stereochemical differentiation of four mono-saccharides using transition metal complexes by electrospray ionization/ion-trap mass spectrometry
    • Carlesso V, Fournier F, Tabet JC. Stereochemical differentiation of four mono-saccharides using transition metal complexes by electrospray ionization/ion-trap mass spectrometry. Eur. J. Mass. Spectrom. 2000; 6: 421.
    • (2000) Eur. J. Mass. Spectrom. , vol.6 , pp. 421
    • Carlesso, V.1    Fournier, F.2    Tabet, J.C.3
  • 26
    • 0029895540 scopus 로고    scopus 로고
    • Determination of the anomeric configuration of glycosyl esters of nucleoside pyrophosphates and polyisoprenyl phosphates by fast-atom bombardment tandem mass spectrometry
    • Wolucka BA, de Hoffmann E, Rush JS, Waechter CJ. Determination of the anomeric configuration of glycosyl esters of nucleoside pyrophosphates and polyisoprenyl phosphates by fast-atom bombardment tandem mass spectrometry. J. Am. Soc. Mass Spectrom. 1996; 7: 541.
    • (1996) J. Am. Soc. Mass Spectrom. , vol.7 , pp. 541
    • Wolucka, B.A.1    De Hoffmann, E.2    Rush, J.S.3    Waechter, C.J.4
  • 27
    • 0020049066 scopus 로고
    • Mass spectra of 1,6:23- and 1,6:34-dianhydro-β-D-hexopyranose derivatives: Formation of cluster ions assisted by participation of neighboring acyloxy groups
    • Kadentsev VI, Kaymarazov AG, Chizhov OS, Cerny M, Trnka T, Turecek F. Mass spectra of 1,6:23- and 1,6:34-dianhydro-β-D-hexopyranose derivatives: formation of cluster ions assisted by participation of neighboring acyloxy groups. Biomed. Mass Spectrom. 1982; 9: 130.
    • (1982) Biomed. Mass Spectrom. , vol.9 , pp. 130
    • Kadentsev, V.I.1    Kaymarazov, A.G.2    Chizhov, O.S.3    Cerny, M.4    Trnka, T.5    Turecek, F.6
  • 28
    • 0032795969 scopus 로고    scopus 로고
    • + ions of acetates on chemical ionization and collision-induced dissociation
    • + ions of acetates on chemical ionization and collision-induced dissociation. J. Mass Spectrom. 1999; 34: 797.
    • (1999) J. Mass Spectrom. , vol.34 , pp. 797
    • Kuzmenkov, I.1    Etinger, A.2    Mandelbaum, A.3
  • 29
    • 0032583441 scopus 로고    scopus 로고
    • Exploring the mechanism of neighboring group assisted glycosylation reactions
    • Nukada T, Berces A, Zgierski MZ, Whitfield DM. Exploring the mechanism of neighboring group assisted glycosylation reactions. J. Am. Chem. Soc. 1998; 120: 13 291.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 13291
    • Nukada, T.1    Berces, A.2    Zgierski, M.Z.3    Whitfield, D.M.4
  • 30
    • 0037073955 scopus 로고    scopus 로고
    • Equatorial contra axial polar substituents. The relation of a chemical reaction to Stereochemical substituent constants
    • Bols M, Liang X, Jensen HH. Equatorial contra axial polar substituents. The relation of a chemical reaction to Stereochemical substituent constants. J. Org. Chem. 2002; 67: 8970.
    • (2002) J. Org. Chem. , vol.67 , pp. 8970
    • Bols, M.1    Liang, X.2    Jensen, H.H.3
  • 31
    • 0000023645 scopus 로고    scopus 로고
    • Experimental and theoretical evidence of through-space electrostatic stabilization of the incipient oxocarbenium ion by an axially oriented electronegative substituent during glycopyranoside acetolysis
    • Miljković M, Yeagley D, Deslongchamps P, Dory Y. Experimental and theoretical evidence of through-space electrostatic stabilization of the incipient oxocarbenium ion by an axially oriented electronegative substituent during glycopyranoside acetolysis. J. Org. Chem. 1997; 62: 7597.
    • (1997) J. Org. Chem. , vol.62 , pp. 7597
    • Miljković, M.1    Yeagley, D.2    Deslongchamps, P.3    Dory, Y.4
  • 32
    • 0142026534 scopus 로고    scopus 로고
    • Influence of the 4,6-O-benzylidene, 4,6-O-phenylboronate, and 4,6-O-polystyrylboronate protecting groups on the Stereochemical outcome of thioglycoside-based glycosylations mediated by 1-benzenesulfinyl piperidine/triflic anhydride and N-iodosuccinimide/trimethylsilyl triflate
    • Crich D, dela Mora M, Vinod AU. Influence of the 4,6-O-benzylidene, 4,6-O-phenylboronate, and 4,6-O-polystyrylboronate protecting groups on the Stereochemical outcome of thioglycoside-based glycosylations mediated by 1-benzenesulfinyl piperidine/triflic anhydride and N-iodosuccinimide/ trimethylsilyl triflate. J. Org. Chem. 2003; 68: 8142.
    • (2003) J. Org. Chem. , vol.68 , pp. 8142
    • Crich, D.1    Dela Mora, M.2    Vinod, A.U.3
  • 34
    • 21344456439 scopus 로고    scopus 로고
    • note
    • Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery JA, Stratmann Jr RE, Burant JC, Dapprich S, Millam JM, Daniels AD, Kudin KN, Strain MC, Farkas O, Tomasi J, Barone V, Cossi M, Cammi R, Mennucci B, Pomelli C, Adamo C, Clifford S, Ochterski J, Petersson GA, Ayala PY, Cui Q, Morokuma K, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Cioslowski J, Ortiz JV, Baboul AG, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Gomperts R, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Andres JL, Gonzalez C, Head-Gordon M, Replogle ES, Pople JA. Gaussian, Inc.: Pittsburgh, PA, 1998.


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