Die Umsetzung von Fructose und Sorbose mit Ammoniak und Aminen

Heyns, Kurt; Eichstedt, Rolf; Meinecke, Karl‐Heinz

doi:10.1002/cber.19550881013

Cited by 34 publications

(11 citation statements)

References 13 publications

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“…Only the characteristic spectral peaks of new compounds are presented. More analytical data are found in other sources (13)(14)(15)(16)(17)(18)(19)(20)(21)(22).…”

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Surface properties of surfactants derived from natural products. Part 1: Syntheses and structure/property relationships—Solubility and emulsification

Piispanen

Persson

Claesson

et al. 2004

J Surfact & Detergents

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Several novel and some previously known, mostly sugar-based, surfactants have been synthesized and some of their surface properties have been characterized and compared with those of commercial nonylphenol ethoxylates. The surfactant solubility in water, ethanol, and dodecane was studied. The properties of these compounds as emulsification agents in systems composed of the surfactant with water/isopropyl myristate, water/rapeseed oil, and water/dodecane are presented. The aqueous solubility of the surfactants follows the general trend expected from their hydrophilic-lipophilic balance according to Griffin (HLBG), but it is also clear that the nature of the headgroup and the structure of the nonpolar part affect the solubility in a manner not captured in the standard HLBG concept. An ester or amine group as the connecting unit between the hydrophile and the hydrophobe produces a more water-soluble surfactant than the corresponding amide derivative. Some effective emulsifiers were found. For instance, the surfactants with a dehydroabietic nonpolar group appear to be promising emulsifiers. Most sugar-based surfactants were able to form macroemulsions of up to around 2 wt/vol% of oil. The stability of many of these emulsions was very high, extending for months.

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“…Only the characteristic spectral peaks of new compounds are presented. More analytical data are found in other sources (13)(14)(15)(16)(17)(18)(19)(20)(21)(22).…”

Section: Methodsmentioning

confidence: 99%

“…Monomethyl polyethyleneglycol (PEG-750) ester of dehydroabietic acid (22). The compound was prepared as previously described (17) …”

Section: -Deoxy-2-dehydroabietoyl-amido-d-glucopyranosementioning

confidence: 99%

Surface properties of surfactants derived from natural products. Part 1: Syntheses and structure/property relationships—Solubility and emulsification

Piispanen

Persson

Claesson

et al. 2004

J Surfact & Detergents

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“…These reactions proceed through many stages, starting with glucosylamines (Schiff bases), fructosamines (Amadori compounds) (3,4), and aminoaldoses (Heyns compounds) (5,6) and ultimately lead to the formation of irreversible end products, which include crosslinks, aromatic heterocycles (2,7,8), and oxidized compounds (9,10), that are designated collectively as advanced glycation end products (AGEs) (11). The concentrations of these products are elevated in diabetes, and evidence from numerous studies suggest that nonenzymatic glycation and AGE formation may be important in the etiology of diabetes complications (12)(13)(14).…”

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confidence: 99%

Human Fructosamine-3-Kinase

2001

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Nonenzymatic glycation appears to be an important factor in the pathogenesis of diabetic complications. Key early intermediates in this process are fructosamines, such as protein-bound fructoselysines. In this report, we describe the purification and characterization of a mammalian fructosamine-3-kinase (FN3K), which phosphorylates fructoselysine (FL) residues on glycated proteins, to FL-3-phosphate (FL3P). This phosphorylation destablilizes the FL adduct and leads to its spontaneous decomposition, thereby reversing the nonenzymatic glycation process at an early stage. FN3K was purified to homogeneity from human erythrocytes and sequenced by means of electrospray tandem mass spectrometry. The protein thus identified is a 35-kDa monomer that appears to be expressed in all mammalian tissues. It has no significant homology to other known proteins and appears to be encoded by genomic sequences located on human chromosomes 1 and 17. The lability of FL3P, the high affinity of FN3K for FL, and the wide distribution of FN3K suggest that the function of this enzyme is deglycation of nonenzymatically glycated proteins. Because the condensation of glucose and lysine residues is an ubiquitous and unavoidable process in homeothermic organisms, a deglycation system mediated by FN3K may be an important factor in protecting cells from the deleterious effects of nonenzymatic glycation. Our sequence data of FN3K are in excellent agreement with a recent report on this enzyme by Delpierre et al.

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“…To a 10% solution of 9 (10.5 g, 20.7 mmol) in pyridine, acetic anhydride (50 mL, 528.9 mmol) was added dropwise at 0°C, a catalytic amount of dimethylaminopyridine was added and the reaction kept at room temperature for 16 h. The solvent was removed under reduced pressure, the residue dissolved in CH 2 Cl 2 and the solution was consecutively washed with 6% HCl and sat aqueous NaHCO 3 , then dried over MgSO 4 . The crude product was precipitated from diisopropyl ether, collected by filtration and dried over P 2 N-Benzylnigerosamine (13). Following the general procedure for the Heyns rearrangement in a typical experiment, turanose 11 (3 g, 8.8 mmol) was reacted with benzylamine (7.5 mL, 68.7 mmol) and the mixture stirred at 40°C for 4 days, when TLC showed the condensation product as the main component in the mixture.…”

Section: General Methodsmentioning

confidence: 99%

“…NMR spectra were recorded on a Varian INOVA 500 operating at 499.925 MHz 13. C NMR spectra were recorded at 75.47 or 50.29 MHz on a BRUKER MSL 300 or on a Varian Gemini 200.…”

mentioning

confidence: 99%

An Exceptionally Simple Chemical Synthesis ofO‐Glycosylatedd‐Glucosamine Derivatives by Heyns Rearrangement of the CorrespondingO‐Glycosyl Fructoses

Stütz¹,

Dékány²,

Eder³

et al. 2003

Journal of Carbohydrate Chemistry

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2-N-Acetyl-4-O-(b-D-galactopyranosyl)-D-glucosamine (N-acetyl-D-lactosamine), a very important building block of biologically relevant oligosaccharides such as sialyl Lewis x , is easily accessible via the Heyns rearrangement of the corresponding Oglycosylated ketohexose, D-lactulose. This approach can also be extended to other glucosamine derivatives employing suitable O-glycosylated ketoses many of which are commercially available. For example, nigerosamine (3-O-a-D-glucopyranosyl-Dglucosamine) was prepared from turanose (3-O-a-D-glucopyranosyl-D-fructose). In combination with a recently introduced vinylogous amide type N-protecting group, [1,3-dimethyl-2, 4, 6 (1H, 3H, 5H)-trioxopyrimidine-5-ylidene] methyl (DTPM), this access is clearly superior to other routes and eminently suitable for scaling up.

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Die Umsetzung von Fructose und Sorbose mit Ammoniak und Aminen

Cited by 34 publications

References 13 publications

Surface properties of surfactants derived from natural products. Part 1: Syntheses and structure/property relationships—Solubility and emulsification

Surface properties of surfactants derived from natural products. Part 1: Syntheses and structure/property relationships—Solubility and emulsification

Human Fructosamine-3-Kinase

An Exceptionally Simple Chemical Synthesis ofO‐Glycosylatedd‐Glucosamine Derivatives by Heyns Rearrangement of the CorrespondingO‐Glycosyl Fructoses

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