Synthesis of Novel Di‐ and Trisaccharide Mimetics with Non‐Glycosidic Amino Bridges.

Neumann, Janna; Weingarten, Saskia; Thiem, Joachim

doi:10.1002/chin.200723188

Cited by 2 publications

(3 citation statements)

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“…(Meinke & Thiem, 2008) CH 2 -Linked α(2,3)sialylgalactose analogue TOF (CHCA) Synthesized using an Ireland-Claisen rearrangement Chitooligomers Reduction of oligomers produced by enzymolysis to prevent browning Decarboxylated sialic acid dimers TOF By-products of 2,3-dehydro-N-acetyl neuraminic acid synthesis (Horn, et al, 2008) Diblock co-oligomers of tri-Omethylated and unmodified cello-oligosaccharides R-TOF (DHB) Carbohydrate-based nonionic surfactants (Kamitakahara, et al, 2007) Di-and tri-saccharide mimics with amino bridges TOF (DHB) NH Link between non-anomeric positions (Neumann, et al, 2007) Gal-β -(1→4)-GlcNAc TOF, glycans (2-AP)…”

Section: Maldi-ftms (No Matrix)mentioning

confidence: 99%

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

Harvey

2011

Mass Spectrometry Reviews

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This review is the fifth update of the original review, published in 1999, on the application of MALDI mass spectrometry to the analysis of carbohydrates and glycoconjugates and brings coverage of the literature to the end of 2008. The first section of the review covers fundamental studies, fragmentation of carbohydrate ions, use of derivatives and new software developments for analysis of carbohydrate spectra. Among newer areas of method development are glycan arrays, MALDI imaging and the use of ion mobility spectrometry. The second section of the review discusses applications of MALDI MS to the analysis of different types of carbohydrate. Specific compound classes that are covered include carbohydrate polymers from plants, N- and O-linked glycans from glycoproteins, biopharmaceuticals, glycated proteins, glycolipids, glycosides and various other natural products. There is a short section on the use of MALDI mass spectrometry for the study of enzymes involved in glycan processing and a section on the use of MALDI MS to monitor products of the chemical synthesis of carbohydrates with emphasis on carbohydrate-protein complexes and glycodendrimers. Corresponding analyses by electrospray ionization now appear to outnumber those performed by MALDI and the amount of literature makes a comprehensive review on this technique impractical. However, most of the work relating to sample preparation and glycan synthesis is equally relevant to electrospray and, consequently, those proposing analyses by electrospray should also find material in this review of interest.

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Section: Maldi-ftms (No Matrix)mentioning

confidence: 99%

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

Harvey

2011

Mass Spectrometry Reviews

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“…Analytical data were in accordance with the literature. [42] 3-O-(5-Bromopentyl)-1,2:5,6-di-O-isopropylidene-α-Dglucofuranose (19) Pursuant to general procedure GP1, 5.20 g (20.00 mmol) of saccharide 10, 624 mg (26.00 mmol) sodium hydride, and 13.47 mL (100.00 mmol) 1,5-dibromopentane (14) in 75 mL of dry DMF and chromatographic purification on silica gel using a mixture of toluene/acetone (30:1) gave compound 19 as a Glycoconjugated Phthalonitriles 21 colorless oil (4.33 g, 53%). Analytical data were in accordance with the literature.…”

Section: 6-bis(2346-tetra-o-benzyl-β-d-glucopyranosyl)phthalonitmentioning

confidence: 97%

“…10). Therefore, galactose 2 was reacted with 2-benzyloxyethyl tosylate (42) dry ethyl acetate. With these additional synthetic steps, product quantities increased and overall yields of 55% for 36 and 34% for 37 were obtained.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Glycoconjugated Phthalonitriles for New Phthalocyanine-Based Photosensitizers

Crucius

Hanack

Ziegler

2015

Journal of Carbohydrate Chemistry

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Excellent photophysical and photochemical properties completed by magnificent takeup rates in malignant tissues attracted a great deal of interest to the application of glycosylated and glycoconjugated phthalocyanines in photodynamic therapy. In this study we describe the concise synthesis and full characterization of 16 differently 3,6-bisglycoconjugated phthalonitriles 3, 5, 6, 8, and 48-59, which are precursors for a new generation of photosensitizers, namely, nonperipheral glycoconjugated phthalocyanines. The first example for the synthesis of a nonperipheral glycoconjugated zinc phthalocyanine 60 from phthalonitrile 48 is also presented in this work.

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Synthesis of Novel Di‐ and Trisaccharide Mimetics with Non‐Glycosidic Amino Bridges.

Abstract: ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Cited by 2 publications

References 1 publication

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

Synthesis of Glycoconjugated Phthalonitriles for New Phthalocyanine-Based Photosensitizers

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