Quantifying Electronic Effects of Common Carbohydrate Protecting Groups in a Piperidine Model System

Mads Heuckendorff; Christian M. Pedersen; Mikael Bols

doi:10.1002/chem.201002313

Development of a Microwave-assisted Chemoselective Synthesis of Oxime-linked Sugar Linkers and Trivalent Glycoclusters

Pharmaceuticals ◽

10.3390/ph12010039 ◽

2019 ◽

Vol 12 (1) ◽

pp. 39

Author(s):

Katherine McReynolds ◽

Dustin Dimas ◽

Grace Floyd ◽

Kara Zeman

Keyword(s):

Biomedical Applications ◽

Model System ◽

Protecting Groups ◽

Microwave Assisted ◽

Synthetic Procedure ◽

Chemoselective Synthesis ◽

Aqueous Conditions ◽

Acid Stable

A rapid, high-yielding microwave-mediated synthetic procedure was developed and optimized using a model system of monovalent sugar linkers, with the ultimate goal of using this method for the synthesis of multivalent glycoclusters. The reaction occurs between the aldehyde/ketone on the sugars and an aminooxy moiety on the linker/trivalent core molecules used in this study, yielding acid-stable oxime linkages in the products and was carried out using equimolar quantities of reactants under mild aqueous conditions. Because the reaction is chemoselective, sugars can be incorporated without the use of protecting groups and the reactions can be completed in as little as 30 min in the microwave. As an added advantage, in the synthesis of the trivalent glycoclusters, the fully substituted trivalent molecules were the major products produced in excellent yields. These results illustrate the potential of this rapid oxime-forming microwave-mediated reaction in the synthesis of larger, more complex glycoconjugates and glycoclusters for use in a wide variety of biomedical applications.

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Remote Electronic Effects by Ether Protecting Groups Fine-Tune Glycosyl Donor Reactivity

The Journal of Organic Chemistry ◽

10.1021/acs.joc.6b00528 ◽

2016 ◽

Vol 81 (12) ◽

pp. 4988-5006 ◽

Cited By ~ 17

Author(s):

Mads Heuckendorff ◽

Lulu Teressa Poulsen ◽

Henrik H. Jensen

Keyword(s):

Protecting Groups ◽

Electronic Effects ◽

Glycosyl Donor ◽

Fine Tune

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A Protozoan Model for Golgi-Associated Calcification

Proceedings, annual meeting, Electron Microscopy Society of America ◽

10.1017/s0424820100065705 ◽

1971 ◽

Vol 29 ◽

pp. 332-333

Author(s):

D. C. Williams ◽

D. E. Outka

Keyword(s):

Golgi Apparatus ◽

Organic Matrix ◽

Model System ◽

Sequential Formation

Many studies have shown that the Golgi apparatus is involved in a variety of synthetic activities, and probably no Golgi product is more elaborate than the scales produced by various kinds of phytoflagellates. The formation of calcified scales (coccoliths, Fig. 1,2) of the coccolithophorid phytoflagellates provides a particularly interesting model system for the study of biological mineralization, and the sequential formation of Golgi products.The coccoliths of Hymenomonas carterae consist of a scale-like base (Fig. 2 and 4, b) with a highly structured calcified (CaCO3) rim composed of two distinct elements which alternate about the base periphery (Fig. 1 and 3, A, B). Each element is enveloped by a sheath-like organic matrix (Fig. 3; Fig. 4, m).

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Existence of DNA in yeast microbodies

Proceedings, annual meeting, Electron Microscopy Society of America ◽

10.1017/s0424820100082029 ◽

1978 ◽

Vol 36 (2) ◽

pp. 232-233

Author(s):

Masako Osumi ◽

Misuzu Nagano ◽

Hiroko Kazama

Keyword(s):

Catalase Activity ◽

Buoyant Density ◽

Model System ◽

Contour Length ◽

Native State ◽

Normal Alkane ◽

Remarkable Increase ◽

Dna Molecule ◽

Mitochondrial Dnas

We have found that microbodies appeared profusely together with a remarkable increase in catalase activity in normal alkane-grown cells of hydrocarbon-utilizing Candida yeasts, and that the microbodies multiplied by division in these cells. These features of Candida yeasts seem to provide a useful model system for studies on the biogenesis of the microbody. Subsequently, we have succeeded in isolation of Candida microbodies in an apparently native state, as judged biochemically and morphologically. The presence of DNA in the purified microbody fraction thus obtained was proved by the diphenylamine method. DNA molecule of about 15 urn in contour length was released from an isolated microbody. The physicochemical analyses of the microbody DNA revealed that its buoyant density differed from nuclear and mitochondrial DNAs. All these results lead us to the possibility that there is a novel type of DNA in microbodies.

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The coprecipitation of Cr3P and Cr in Cu

Proceedings, annual meeting, Electron Microscopy Society of America ◽

10.1017/s0424820100105886 ◽

1988 ◽

Vol 46 ◽

pp. 764-765

Author(s):

M.J. Witcomb ◽

U. Dahmen ◽

K.H. Westmacott

Keyword(s):

Orientation Relationship ◽

Interface Structure ◽

Model System ◽

Relative Orientation ◽

Age Hardening ◽

Precipitation Behavior ◽

Solution Treated ◽

Small Needle ◽

Diffraction Patterns ◽

Interface Structures

Cu-Cr age-hardening alloys are of interest as a model system for the investigation of fcc/bcc interface structures. Several past studies have investigated the morphology and interface structure of Cr precipitates in a Cu matrix (1-3) and good success has been achieved in understanding the crystallography and strain contrast of small needle-shaped precipitates. The present study investigates the effect of small amounts of phosphorous on the precipitation behavior of Cu-Cr alloys.The same Cu-0.3% Cr alloy as was used in earlier work was rolled to a thickness of 150 μm, solution treated in vacuum at 1050°C for 1h followed by quenching and annealing for various times at 820 and 863°C.Two laths and their corresponding diffraction patterns in an alloy aged 2h at 820°C are shown in correct relative orientation in Fig. 1. To within the limit of accuracy of the diffraction patterns the orientation relationship was that of Kurdjumov-Sachs (KS), i.e. parallel close-packed planes and directions.

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Membrane-associated microtubular areays induced in proximal myelinated processes of dorsal root ganglia by large doses of vitamin B6

Proceedings, annual meeting, Electron Microscopy Society of America ◽

10.1017/s0424820100143468 ◽

1986 ◽

Vol 44 ◽

pp. 368-369

Author(s):

V.J. Montpetit ◽

S. Dancea ◽

L. Tryphonas ◽

D.F. Clapin

Keyword(s):

Animal Model ◽

Endoplasmic Reticulum ◽

Dorsal Root Ganglia ◽

Rough Endoplasmic Reticulum ◽

Dorsal Root ◽

Vitamin B6 ◽

Morphological Changes ◽

Model System ◽

Sensory Nerves ◽

Peripheral Sensory

Very large doses of pyridoxine (vitamin B6) are neurotoxic in humans, selectively affecting the peripheral sensory nerves. We have undertaken a study of the morphological and biochemical aspects of pyridoxine neurotoxicity in an animal model system. Early morphological changes in dorsal root ganglia (DRG) associated with pyridoxine megadoses include proliferation of neurofilaments, ribosomes, rough endoplasmic reticulum, and Golgi complexes. We present in this report evidence of the formation of unique aggregates of microtubules and membranes in the proximal processes of DRG which are induced by high levels of pyridoxine.

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An Ultrastructural Comparison of Hepatocytes from ADH+ and ADH−Peromyscus Maniculatus

Proceedings, annual meeting, Electron Microscopy Society of America ◽

10.1017/s0424820100162612 ◽

1996 ◽

Vol 54 ◽

pp. 30-31

Author(s):

J. T. Ellzey ◽

D. Borunda ◽

B. P. Stewart

Keyword(s):

South Carolina ◽

Adult Male ◽

Uranyl Acetate ◽

Model System ◽

Deer Mice ◽

En Bloc ◽

Genetic Stock ◽

Hepes Buffer ◽

Transmission Electron ◽

Color Scanner

Genetically alcohol deficient deer mice (ADHN/ADHN) (obtained from the Peromyscus Genetic Stock Center, Univ. of South Carolina) lack hepatic cytosolic alcohol dehydrogenase. In order to determine if these deer mice would provide a model system for an ultrastructural study of the effects of ethanol on hepatocyte organelles, 75 micrographs of ADH+ adult male deer mice (n=5) were compared with 75 micrographs of ADH− adult male deer mice (n=5). A morphometric analysis of mitochondrial and peroxisomal parameters was undertaken.The livers were perfused with 0.1M HEPES buffer followed by 0.25% glutaraldehyde and 2% sucrose in 0.1M HEPES buffer (4C), removed, weighed and fixed by immersion in 2.5% glutaraldehyde in 0.1M HEPES buffer, pH 7.4, followed by a 3,3’ diaminobenzidine (DAB) incubation, postfixation with 2% OsO4, en bloc staining with 1% uranyl acetate in 0.025M maleate-NaOH buffer, dehydrated, embedded in Poly/Bed 812-BDMA epon resin, sectioned and poststained with uranyl acetate and lead citrate. Photographs were taken on a Zeiss EM-10 transmission electron microscope, scanned with a Howtek personal color scanner, analyzed with OPTIMAS 4.02 software on a Gateway2000 4DX2-66V personal computer and stored in Excel 4.0.

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Elemental analysis of human erythrocytes

Proceedings, annual meeting, Electron Microscopy Society of America ◽

10.1017/s042482010015318x ◽

1989 ◽

Vol 47 ◽

pp. 242-243

Author(s):

S. A. Livesey ◽

A. A. del Campo ◽

E. S. Griffey ◽

D. Ohlmer ◽

T. Schifani ◽

...

Keyword(s):

Sample Preparation ◽

Elemental Analysis ◽

Human Erythrocyte ◽

Spectroscopic Analysis ◽

Model System ◽

Human Erythrocytes ◽

List Type ◽

Chemical Fixation ◽

Ethanol Dehydration ◽

Lowicryl K4m

The aim of this study is to compare methods of sample preparation for elemental analysis. The model system which is used is the human erythrocyte. Energy dispersive spectroscopic analysis has been previously reported for cryofixed and cryosectioned erythrocytes. Such work represents the reference point for this study. The use of plastic embedded samples for elemental analysis has also been documented. The work which is presented here is based on human erythrocytes which have been either chemically fixed and embedded or cryofixed and subsequently processed by a variety of techniques which culminated in plastic embedded samples.Heparinized and washed erythrocytes were prepared by the following methods for this study :(1). Chemical fixation in 4% paraformaldehyde/0.25% glutaraldehyde/0.2 M sucrose in 0.1 M Na cacodylate, pH 7.3 for 30 min, followed by ethanol dehydration, infiltration and embedding in Lowicryl K4M at -20° C.

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