Amphimedosides A–C: Synthesis, Chemoselective Glycosylation, And Biological Evaluation

Langenhan, Joseph M.; Mullarky, Edouard; Rogalsky, Derek K.; Rohlfing, James R.; Tjaden, Anja E.; Werner, Halina M.; Rozal, Leonardo M.; Loskot, Steven A.

doi:10.1021/jo302640y

Cited by 10 publications

(8 citation statements)

References 39 publications

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“…Milder conditions (3:1 DMF/AcOH, 40 °C, 6 h) enabled the desired tetrose neoglycoside in 44% isolated yield. Consistent with previous studies, − the β-anomer was the predominate product with notable exceptions including d -erythroside, d -arabinoside, d -riboside, 2′-deoxy- d -glucoside, and d -mannoside (Table , Figure ).…”

Section: Resultssupporting

confidence: 90%

“…With respect to the latter, while naturally occurring tetracycline glycosides have been reported, including dactylocycline, TAN-1518, and SF2575, the systematic differential glycosylation of the tetracycline scaffold has not been pursued. Among emerging strategies to enable the rapid systematic differential glycosylation of complex natural products, , neoglycosylation employs a mild chemoselective reaction between free reducing sugars and alkoxyamine-bearing neoaglycons. − As a result, neoglycosylation avoids the many protection/deprotections or anomeric activation manipulations typically required for glycoside synthesis by conventional methods . Inspired by both the impact of 9-glycylamino-tetracycline modification upon activity and the striking structural similarity between the tigecycline 9-glycylamino spacer and previously reported glycyl-based linkers for neoglycosylation, , herein we report the synthesis of a set of differentially glycosylated 9-(methoxyglycyl)amino-doxycyclines as a simple tetracycline model.…”

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confidence: 99%

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Synthesis and Antibacterial Activity of Doxycycline Neoglycosides

et al. 2013

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A set of 37 doxycycline neoglycosides mediated via a C9 alkoxyamino-glycyl-based spacer reminiscent to that of tigecycline were prepared. The in vitro antibacterial assays against representative drug resistant Gram negative and Gram positive strains revealed a sugar-dependent activity profile and one doxycycline neoglycoside, the 2′-amino-α-D-glucoside conjugate, to rival that of the parent pharmacophore. In contrast, the representative tetracycline-susceptible strains E. coli 25922 was found to be relatively responsive to a range of doxycycline neoglycosides. This study also extends the use of aminosugars in the context of neoglycosylation via a simple two step strategy anticipated to be broadly applicable for neoglycorandomization.

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Section: Resultssupporting

confidence: 90%

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confidence: 99%

Synthesis and Antibacterial Activity of Doxycycline Neoglycosides

et al. 2013

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“…630 Synthesis conrmed the structures of amphimedosides A-C (Amphimedon sp.). 672,673 Pyrinodemins G-I 646-648 are bis-3alkylpyridinium alkaloids from Amphimedon sp. (Okinawa), although the exact positioning of the alkyne functionalities is uncertain and hence the compounds are likely a mixture of related congeners.…”

Section: Spongesmentioning

confidence: 99%

Marine natural products

et al. 2015

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This review covers the literature published in 2013 for marine natural products (MNPs), with 982 citations (644 for the period January to December 2013) referring to compounds isolated from marine microorganisms and phytoplankton, green, brown and red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and microorganisms. The emphasis is on new compounds (1163 for 2013), together with the relevant biological activities, source organisms and country of origin. Reviews, biosynthetic studies, first syntheses, and syntheses that lead to the revision of structures or stereochemistries, have been included.

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“…Methoxyamine based neoglycosylation is often carried out under mildly acidic conditions, either in buffered aqueous (NaOAc/AcOH) solutions (Matsubara, et al 2005) or in mixtures of organic solvents containing acetic acid (Langenhan, et al 2013, Peri, et al 2004). DMF/AcOH 3:1 has been frequently the choice due to its high dissolving power for both lipophilic and hydrophilic compounds.…”

Section: Resultsmentioning

confidence: 99%

Development of a multifunctional aminoxy-based fluorescent linker for glycan immobilization and analysis

et al. 2016

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Glycan arrays have become a technique of choice to screen glycan-protein interactions in a high-throughput manner with high sensitivity and low sample consumption. Here, the synthesis of a new multifunctional fluorescent linker for glycan labeling via aminoxy ligation and immobilization is described; the linker features a fluorescent naphthalene group suitable for highly sensitive high-performance liquid chromatography-based purification and an azido- or amino-modified pentanoyl moiety for the immobilization onto solid supports. Several glycoconjugates displaying small sugar epitopes via chemical or chemoenzymatic synthesis were covalently attached onto a microarray support and tested with lectins of known carbohydrate binding specificity. The glycan library was extended using glycosyltransferases (e.g. galactosyl-, sialyl- and fucosyltransferases); the resulting neoglycoconjugates, which are easily detected by mass spectrometry, mimic antennal elements of N- and O-glycans, including ABH blood group epitopes and sialylated structures. Furthermore, an example natural plant N-glycan containing core α1,3-fucose and β1,2-xylose was also successfully conjugated to the fluorescent linker, immobilized and probed with lectins as well as antihorseradish peroxidase. These experiments validate our linker as being a potentially valuable tool to study glycozyme and lectin specificities, sensitive enough to allow purification of natural glycans.

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Amphimedosides A–C: Synthesis, Chemoselective Glycosylation, And Biological Evaluation

Cited by 10 publications

References 39 publications

Synthesis and Antibacterial Activity of Doxycycline Neoglycosides

Synthesis and Antibacterial Activity of Doxycycline Neoglycosides

Marine natural products

Development of a multifunctional aminoxy-based fluorescent linker for glycan immobilization and analysis

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