Structure determination of N-acetyl amino sugar derivatives and disaccharides by gas chromatography and mass spectroscopy

Coduti, Phillip L.; Bush, C. Allen

doi:10.1016/0003-2697(77)90004-5

Cited by 26 publications

(7 citation statements)

References 15 publications

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“…The ions at m/z 191 ( ed ), 204 ( eo ) and 305 ( ep ) are of very low relative abundance, with m/z 217 ( z ) as the base peak (ignoring m/z 73 whose relative abundance can vary because of background interference). In the spectrum of the N ‐acetylamino analog, the peak at m/z 217 shifts to m/z 186 (Coduti & Bush, ), confirming inclusion of C2 as indicated above. The ion at m/z 205 ( eb ) is more abundant than in the spectra of the pyranosides, an observation that can be accounted for by α‐cleavage of the C4‐C5 bond.…”

Section: Trimethylsilyl Derivativesmentioning

confidence: 65%

“…Peaks were not found to differentiate the 1→5 and 1→6‐linkages. Coduti and Bush () report that the spectrum of the 1→6‐linked isomer of the TMS derivative of (GlcNAc) 2 contains a moderately abundant ion at m/z 552 ( fc ) which is absent in the spectrum of the 1→4 linked isomer.…”

Section: Trimethylsilyl Derivativesmentioning

confidence: 99%

“…In the spectrum of N-acetylglucosamine this peak appears at m/z 173 reflecting the replacement of the 2-TMSO group with NHAc (Coduti & Bush, 1977). In glucosamine, where there is a (CH 3 ) 3 Si-NH-link, the ion is at m/z 203 (Kärkkäinen & Vihko, 1969).…”

Section: Iic3a Monosaccharidesmentioning

confidence: 99%

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Mass Spectrometric Fragmentation of Trimethylsilyl and Related Alkylsilyl Derivatives

Harvey

Vouros

2019

Mass Spectrometry Reviews

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This review describes the mass spectral fragmentation of trimethylsilyl (TMS) and related alkylsilyl derivatives used for preparing samples for analysis, mainly by combined gas chromatography and mass spectrometry (GC/MS). The review is divided into three sections. The first section is concerned with the TMS derivatives themselves and describes fragmentation of derivatized alcohols, thiols, amines, ketones, carboxylic acids and bifunctional compounds such as hydroxy‐ and amino‐acids, halo acids and hydroxy ethers. More complex compounds such as glycerides, sphingolipids, carbohydrates, organic phosphates, phosphonates, steroids, vitamin D, cannabinoids, and prostaglandins are discussed next. The second section describes intermolecular reactions of siliconium ions such as the TMS cation and the third section discusses other alkylsilyl derivatives. Among these latter compounds are di‐ and trialkyl‐silyl derivatives, various substituted‐alkyldimethylsilyl derivatives such as the tert‐butyldimethylsilyl ethers, cyclic silyl derivatives, alkoxysilyl derivatives, and 3‐pyridylmethyldimethylsilyl esters used for double bond location in fatty acid spectra. © 2019 Wiley Periodicals, Inc. Mass Spec Rev 0000:1–107, 2019

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Section: Trimethylsilyl Derivativesmentioning

confidence: 65%

Section: Trimethylsilyl Derivativesmentioning

confidence: 99%

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Mass Spectrometric Fragmentation of Trimethylsilyl and Related Alkylsilyl Derivatives

Harvey

Vouros

2019

Mass Spectrometry Reviews

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“…Sweeley et al (1956) introduced a simple and efficient method for the preparation of TMS ethers of a variety of carbohydrates, including di-, tri-, and tetrasaccharides. The application of their methodology to the analysis of carbohydrates has been reported by several authors (Kimura et al, 1969;Percival, 1967;Haverkamp et al, 1971;Coduti and Bush, 1977;Thompson et al, 1978;Laker, 1979). The problem with this methodology in the analysis of complex carbohydrate mixtures is the presence of tautomeric forms of the reducing sugars.…”

Section: Introductionmentioning

confidence: 91%

Analysis and Quantitation of Minor Di‐ and Trisaccharides in Honey, Using Capillary Gas Chromatography

Low¹,

Sporns²

1988

Journal of Food Science

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Methodology is introduced to separate and quantitate most of the diand trisaccharides composed of glucose and fructose moieties, found in honey. At least twelve closely related disaccharides and seven trisaccharides were successfully identified and quantitated employing a combination of reduction and trimethylsilylation followed by either temperature programmed (disaccharides) or isothermal (trisaccharides) gas chromatography. The oligosaccharides in honey, representing approximately 3% of the total sugars, could be isolated using preparative HPLC and analyzed using the aforementioned gas chromatographic methodology. In addition, these oligosaccharides could also be analyzed without employing a preparative HPLC separation by using a concomitantly larger sample volume. Palatinose, not previously reported in honey, was found in many honey samples.

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“…Comparison of these mass spectra with those published by Coduti and Bush [8] leaves no question that the GLC peaks in both the chitinase digest and the chitobiose standard represent chitobiose.…”

Section: Discussionmentioning

confidence: 94%

Evidence for chitin synthesis in an insect cell line

Marks

Balke

Klosterman

1983

Arch Insect Biochem Physiol

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Structure determination of N-acetyl amino sugar derivatives and disaccharides by gas chromatography and mass spectroscopy

Cited by 26 publications

References 15 publications

Mass Spectrometric Fragmentation of Trimethylsilyl and Related Alkylsilyl Derivatives

Mass Spectrometric Fragmentation of Trimethylsilyl and Related Alkylsilyl Derivatives

Analysis and Quantitation of Minor Di‐ and Trisaccharides in Honey, Using Capillary Gas Chromatography

Evidence for chitin synthesis in an insect cell line

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