Mass spectrometry of oligosaccharides

Kochetkov, N. K.; Chizhov, O. S.; Molodtsov, N.V.

doi:10.1016/0040-4020(68)88156-6

Cited by 88 publications

(35 citation statements)

References 8 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The most common methods for sequence determination of saccharides involve permethylation or peracetylation, both of which are however time consuming. [1][2][3][4][5][6][7][8] Several workers have previously employed underivatized carbohydrates for structural characterization and such studies have generally involved the negative ion mode. [9][10][11][12][13] For obtaining molecular weight information positive ion fast atom bombardment mass spectrometry of underivatized di-and trisaccharides proved to be of great value, but linkage and sequence information for disaccharides was not readily obtained because spectral differences between isomers were relatively small.…”

mentioning

confidence: 99%

Unexpected gas-phase reactions of some underivatized disaccharides and of proton-bound dimers of monosaccharides by liquid-assisted secondary ion mass spectrometry

Zapfe

Müller

1998

Rapid Commun. Mass Spectrom.

View full text Add to dashboard Cite

The positive liquid secondary ion mass spectrometry (LSIMS) spectra and LSIMS mass-analyzed ion kinetic energy/collision activated dissociation (MIKE/CAD) spectra of three underivatized monosaccharides and fourteen disaccharides are discussed. Discrimination of the glycosidic linkage position and determination of the reducing end and the sequence of disaccharides are not possible, owing to the isomerization of bonds, in addition to the elimination of both sugar units as an anhydro sugar. Furthermore the fragmentations of [2MH] ions of monosaccharides, which appear to yield disaccharide ions on CAD, are discussed. # 1998 John Wiley & Sons, Ltd. Received 11 August 1997; Revised 6 March 1998; Accepted 10 March 1998 The elucidation of sequence, linkage and conformations of carbohydrates are all of intense current interest. The importance of this structural identification problem is such that a more extensive and diverse contribution by mass spectrometry is desirable. The most common methods for sequence determination of saccharides involve permethylation or peracetylation, both of which are however time consuming.1-8 Several workers have previously employed underivatized carbohydrates for structural characterization and such studies have generally involved the negative ion mode.9-13 For obtaining molecular weight information positive ion fast atom bombardment mass spectrometry of underivatized di-and trisaccharides proved to be of great value, but linkage and sequence information for disaccharides was not readily obtained because spectral differences between isomers were relatively small.14 We wish to report on the positive ion mass spectrometry in order to give a possible explanation for the impossibility of an unambiguous identification of the type of linkage and sequence of disaccharides.

show abstract

mentioning

confidence: 99%

Unexpected gas-phase reactions of some underivatized disaccharides and of proton-bound dimers of monosaccharides by liquid-assisted secondary ion mass spectrometry

Zapfe

Müller

1998

Rapid Commun. Mass Spectrom.

View full text Add to dashboard Cite

show abstract

“…Pertrimethylsilyl derivatives of a 1-4 linked disaccharide have been found to form fragment I1 which subsequently loses a methyl radical to give fragment 111 (12). The decomposition of the molecular-ion to fragment V, characteristic of the reducing residue, has been demonstrated (13). In the present investigation, fragments I-IV, derived from the non-reducing moiety all had the correct nzle to have incorporated the substituent.…”

Section: "mentioning

confidence: 61%

Preparation of 6′-Substituted Maltoses

Melton¹,

Slessor²

1973

Can. J. Chem.

View full text Add to dashboard Cite

show abstract

“…Thus, the fragment at mle 99 (3, 7, 9, 11) is relatively abundant in the 2,5-furanoses, the 1,5-pyranoses, and the 1, ion at m / e 69 (7, 12, 13) (protonated furan) is always present (6, 9, 1 1 , 14), m / e 319 (or its equivalent for the trimethylsilyl in all derivatives of the hex-and pentosuloses and, in spite of derivatives (8,15,16)), m / e 217 (greater than m / e 204 for the their higher abundance in the furanose forms, is not indicative trimethylsilyl derivatives (15, 16, 17)), and m / e 83 (for the of the ring type.…”

Section: B the Ring Type Detennitzationmentioning

confidence: 99%

“…As in the compounds of the preceding structural unit, compounds 8 and 9 show fragments at rnle 101, 1 15, and 129 which must proceed from a rearrangement (9). Characteristic of this structural unit (7,19,22) are abundant peaks at mle 72, mle 1 13 (Me2C-0-CH=CH-CHO shifted by 1 19 (7, 9) in deuterated analogues), mle 85 (shifted by 88), mle 71 (shifted by 74), and mle 117, as shown in Table 8B.…”

Section: J the 46-0-isopropylidene Structural Itnitmentioning

confidence: 99%

Gas chromatography – mass spectrometry of osulose derivatives: O-trimethylsilyl, O-acetyl, O-isopropylidene, methyl glycosides, and 1,1-dimethyl acetals

Ruiz¹,

Travesedo²,

Martínez³

1984

Can. J. Chem.

View full text Add to dashboard Cite

Del~(lrtltwru of Olgorlic Chernisrry, Faculty cfSc.ier~c.~, Ut~i\~c~r.si/y r?f'M~rrcia. Mirrcia, Spirit1Reccived October 2 1 , 1982' PEDRO ANTONIO GARC~A RUIZ, INMACULADA CARTAGENA TRAVESEDO, and ANTONIO SOLER MARTINEZ. Can. J. Chem. 62, 870 (1984).Structure determination of the 0-trimethylsilyl, 0-acetyl, and 0-isopropylidene derivatives of some hexosuloses, pentosuloses, and one tetrosulose, as well as their methyl glycosides and 1,l-dimethyl acetals has been achieved by gas chromatography -mass spectrometry.By study based on the qualitative and quantitative differences in the 36 derivatives obtained, and their analogues prepared from tetradeuterio methanol and/or hexadeuterio acetone, and comparison with results reported in the literature, criteria for the unambiguous determination of the structural grouping are proposed. The relative abundance of each compound when the osulose forms more than one isomeric derivative in the same reaction, as well as chromatographic data for the isolated products, are reported.PEDRO ANTONIO GARCIA RUIZ, INMACULADA CARTAGENA TRAVESEDO et ANTONIO SOLER MARTINEZ. Can. J. Chem. 62, 870 (1984).Faisant appel B la chromatographie en phase gazeuse couplee B la spectromktrie de masse, on a determine la structure des derives 0-trimkthylsilyl, 0-acetyl et 0-isopropylidkne des quelques hexosuloses, pentosuloses et d'un tCtrosulose ainsi que de leurs glucosides de methyle et de leurs dimethyl-l ,I acetals.En se basant, d'une part, sur les differences qualitatives et quantitatives observkes dans les 36 derives obtenus et dans leurs analogues preparks B partir du tktradeutkro methanol et/ou de l1hexadeutCro acetone et, d'autre part, sur une comparaison avec les rksultats rapport& dans la litteratwe, on propose des criteres pour la determination non-ambigue des caracteristiques de structure. On rapporte aussi les donnees chromatographiques pour les produits isoles ainsi que les abondances relatives de chaque compose form6 lorsque les osuloses forment plus d'un derive isomkre dans la m&me reaction.[Traduit par le journal] Introduction Although, glc-ms is a powerful tool for the structural elucidation (1) of the sugars, and analyses of some of the volatile derivatives of aldoses (2) and ketoses (3) that have been reported, until now no efficient method for the determination of the volatile derivatives of the osuloses has been published.The present paper describes studies by electron impact mass spectrometry of four types of volatile derivatives of eight osuloses. These were the isopropylidene acetals, trimethylsilyl ethers, and acetate esters of the free sugars, and the isopropylidene acetals of the methyl glycosides.

show abstract

Mass spectrometry of oligosaccharides

Cited by 88 publications

References 8 publications

Unexpected gas-phase reactions of some underivatized disaccharides and of proton-bound dimers of monosaccharides by liquid-assisted secondary ion mass spectrometry

Unexpected gas-phase reactions of some underivatized disaccharides and of proton-bound dimers of monosaccharides by liquid-assisted secondary ion mass spectrometry

Preparation of 6′-Substituted Maltoses

Gas chromatography – mass spectrometry of osulose derivatives: O-trimethylsilyl, O-acetyl, O-isopropylidene, methyl glycosides, and 1,1-dimethyl acetals

Contact Info

Product

Resources

About