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1

Achmatowicz rearrangement - 50 years of application

Grynkiewicz Grzegorz, Bielski Roman

Polish Technical Review

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2020

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No. 4

16--27

EN

Chemical sciences proved instrumental in formulating theories and in providing materials which are crucial for development of contemporary technical civilization. Methods of chemical synthesis, necessary for supply of materials designed for specific technical needs have attained efficiency, which allows preparation of even most complicated molecules encountered in Nature. Academic stereo- and enantioselective total syntheses of natural products (such as: alkaloids, peptides, isoprenoids, lipids, carbohydrates and phenolics) are generally regarded as the top achievements of XX century organic chemistry. Along the line, this paper recalls ingenious project of total synthesis from simple furan derivatives, of pyranes and pyranosides, basic stuff of natural carbohydrates, suitably functionalized for a stepwise conversion into variety of sugar structures. The project designed in the Institute of Organic Chemistry, Polish Academy of Sciences in Warsaw, began its proof of principle experimental validation in 1970. Its success led to a widespread application of what is presently known as the Achmatowicz reaction/Achmatowicz rearrangement for syntheses of simple and complex, oxygen and nitrogen heterocyclic systems, including great variety of natural products.

PL

Nauki chemiczne odegrały kluczową rolę w kształtowaniu zarówno podstaw teoretycznych jak i zaplecza materialnego współczesnej cywilizacji przemysłowej. Metody syntezy chemicznej, niezbędne do wytwarzania materiałów technicznych o pożądanych właściwościach, osiągnęły sprawność pozwalającą na otrzymanie związków odpowiadających cząsteczkom organicznym pochodzenia biologicznego, o najwyższym stopniu złożoności. Syntezy totalne, stereo- i enancjoselektywne, związków naturalnych (alkaloidów, peptydów, izoprenoidów, lipidów, węglowodanów i związków fenolowych) uznano za najważniejsze osiągnięcia klasycznej chemii organicznej. Poniżej przedstawiamy genezę i rozwój projektu totalnej syntezy z prostych pochodnych furanu, wielofunkcyjnych piranów i piranoz - zasadniczej heterocyklicznej sześcioczłonowej struktury pierścieniowej naturalnych cukrów, glikozydów i ich oligomerycznych pochodnych, opracowanego w Instytucie Chemii Organicznej PAN w Warszawie, który w 1970-tym roku osiągnął zrealizowaną z powodzeniem fazę weryfikacji doświadczalnej. Osiągnięcie, które zyskało nazwę reakcji (przegrupowania) Achmatowicza, stanowi obecnie jedno z popularniejszych narzędzi stereokontrolowanej syntezy tlenowych i azotowych związków heterocyklicznych.

2

Badania nad enzymatyczną hydrolizą polisacharydów w słomie sorgo i konwersją monosacharydów do etanolu

Kotarska K., Dziemianowicz W., Świerczyńska A.

Przemysł Chemiczny

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2018

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T. 97, nr 12

2189--2191

PL

Przedstawiono wyniki badań rozkładu hydrolitycznego polisacharydów w biomasie lignocelulozowej oraz stopnia wykorzystania uzyskanych monosacharydów w procesie tworzenia etanolu. Konwersję polisacharydów do cukrów prostych przeprowadzono przy użyciu preparatów enzymatycznych i ich kombinacji. Zastosowanie łącznie celulazy, hemicelulazy i ksylanazy pozwoliło na uzyskanie wydajności alkoholu ze słomy sorgo w ilości 13,6 dm³/100 kg surowca.

EN

Sorghum straw polysaccharides were hydrolyzed by using cellulase to monosaccharides and fermented to EtOH by using distillery yeast. The EtOH yield was ca. 13.6 L/100 kg of raw material.

3

The magnetic field stimulation system applied on strawberry fruits

Zaguła G., Puchalski C., Czernicka M., Bajcar M., Saletnik B., Woźny M., Szeregii E.

ECONTECHMOD : An International Quarterly Journal on Economics of Technology and Modelling Processes

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2017

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Vol. 6, No 1

117--122

EN

This paper presents an influence of three different magnetic fields stimulation systems for growing strawberry fruits: permanent magnetic field generated by neodymium magnets, ”high” strengths slow varying amplitudes magnetic fields generated by coreless solenoids supplied by autotransformer and low-frequency and low-amplitude sinusoidal magnetic fields generator created for this research. The system is controlled by computer and allows for an independent control of up to 10 induction coils inducing magnetic fields with amplitudes from 0.1μT to 150μT and frequencies from 0.1Hz to 100Hz. The proposed set-up was used during the growing seasons for strawberry plants stimulation. An increase in the extract level was observed in the case of the alternating magnetic field stimulation with the parameters: frequency – from 50Hz to 100Hz and amplitude – from 50μT to 100μT.

4

Metody określania struktury polisacharydów

Samaszko-Fiertek J., Kuźma M., Dmochowska B., Ślusarz R., Madaj J.

Wiadomości Chemiczne

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2016

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[Z] 70, 5-6

299--318

EN

Sequencing of polysaccharides is difficult to achieve because of the heterogeneous nature of the polysaccharide structure, high molecular weight (the size of a polysaccharide varies between approximately 16,000 and 16,000,000 daltons (Da)), and polydispersity of the polymer chains. The following information is essential to determine the primary structure of a polysaccharide: • monosaccharide composition: nature and molar ratios of the monosaccharide building blocks; • relative configuration of monosaccharides: d or l; • anomeric configuration: α- or β-configuration of the glycosidic linkage; • ring size: presence and distinction of furanosidic and pyranosidic rings; • linkage patterns: linkage positions between the monosugars and branches; • sequences of monosaccharide residues in the repeating units; • substitutions: position and nature of OH–modifications, such as O–phosphorylation, acetylation, O-sulfation, etc.; • molecular weight and molecular weight distribution. A polysaccharide extracted from plant materials or food products is usually purified before being subjected to structural analysis. The first step of characterizing a polysaccharide is the determination of its purity, which is reflected by its chemical composition, including total sugar content, level of uronic acids, proteins, ash, and moisture of the preparation. The second step is the determination of monosaccharide composition, which will unveil structural information such as the number of monosaccharides present in the polysaccharide and how many of each sugar unit. NMR spectroscopy has become the most powerful and noninvasive physicochemical technique for determining polysaccharide structures. It can provide detailed structural information of carbohydrates, including identification of monosaccharide composition, elucidation of α- or β-anomeric configurations, establishment of linkage patterns, and sequences of the sugar units in oligosaccharides and/or polysaccharides. Monosaccharide composition can be determined also by analysis of totally acid hydrolyzed polysacharide using high performance liquid chromatography (HPLC) or gas chromatography (GC). The ring size and glycosidic linkage positions of sugar units in a polysaccharide could be established by methylation analysis and/or cleavage reduction. The anomeric configuration is conventionally determined by oxidation, and this method can be combined with mass spectrometry to obtain more structural information.

5

The effect of traumatic acid on the growth, metabolite content and antioxidant activity in Wolffia arrhiza (L.) Wimm. (Lemnaceae)

Pietryczuk A., Czerpak R.

Oceanological and Hydrobiological Studies

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2012

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Vol. 41, No. 1

24-34

EN

The research presented here was conducted in order to determine the influence of exogenous traumatic acid (TA) on the growth, metabolism, and antioxidative activity of vascular water plant, Wolffia arrhiza Wimm. The research was concerned with TA influences, in concentrations of 10^-8 M – 10^-4 M, on fresh W. arrhiza, and on primary metabolites, such as monosaccharides, proteins, chlorophylls a and b, and carotenoids. It was determined that TA causes a substantial increase in these metabolites compared to the control, especially at concentrations of 10^-7 – 10^-6 M. Polyacrylamide gel electrophoresis of proteins (SDS-PAGE) was conducted in order to specify in more detail the qualitative changes in proteins, whose synthesis is stimulated by TA. Under the influence of TA W. arrhiza cells saw an induction of de novo synthesis of 3 proteins with molecular weights of 10, 58, and 90 kDa. It was proven that 10^-7 – 10^-6 M concentrations of TA also increase photosynthesis intensity and the activity of antioxidative enzymes (ascorbate peroxidase, catalase, glutathione reductase, and superoxide dismutase). In cells treated with exogenous TA, lipids' peroxidation decreases (expressed as a drop in malonyl dialdehyde) and sulfhydryl (SH) groups in proteins increase. Based on our research, TA plays an important role in the regulation of growth and metabolism in W. arrhiza. Our results also show that TA possibly participates in the activation of antioxidant enzymes and its probable participation in the metabolic responses of lower water plants to oxidative stresses.

6

Galactose monoacrylate as a new monomer in gelcasting process

Szudarska A., Mizerski T., Szafran M.

Archives of Metallurgy and Materials

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2011

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Vol. 56, iss. 4

1211-1215

EN

The present work shows the results of following the recently developed trend to design new low toxic monomers which can be applied in gelcasting process. New compound, 6-O-acryloyl-D-galactose (galactose monoacrylate) has been synthesised and its effectiveness as processing agent has been studied. The results are compared with those reported so far regarding applying some other new monomers - 3-O-acryloyl-D-glucose and glycerol monoacrylate in gelcasting technology. The influence of spatial structure of obtained monomers on rheological properties of alumina suspensions and properties of green bodies is discussed as well.

PL

Artykuł przedstawia wyniki badań dotyczących zastosowania nowozsyntezowanej akrylowej pochodnej galaktozy jako monomeru w procesie odlewania żelowego. Opracowano metode syntezy 6-O-akryloilogalaktozy oraz zbadano jej role i efektywność w procesie. Wyniki porównano z wcześniejszymi pracami z tego zakresu, dotyczącymi zastosowania innych nowych nietoskycznych monomerów – 3-O-akryloiloglukozy oraz monoakrylanu glicerolu, szukając wpływu budowy przestrzennej cząsteczek monomeru na właściwości reologiczne mas lejnych z tlenku glinu i właściwosci odlanych z nich wyrobów.

7

The effect of sodium amidotrizoate on the growth and content of various metabolites in the green alga Chlorella vulgaris Beijerinck

Pietryczuk A., Czerpak R., Popławska B., Wolski T.

Oceanological and Hydrobiological Studies

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2010

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Vol. 39, No.1

61-73

EN

The aim of this work is to detect how 3,5-diacetamido-2,4,6-triiodosodium benzoate (sodium amidotrizoate), a synthetic derivative of the anti-auxin triiodonezoic acid (TIBA), influences the growth and content of primary metabolites in the green alga Chlorella vulgaris Beijerinck. It strongly suppressed cell number by 6–20%, chlorophyll a by 6–14%, chlorophyll b by 20–24%, total carotenoids by 7–13% and monosaccharides by 7–8% at the concentration of 10^-4 M, in comparison to the control. On the other hand, sodium amidotrizoate applied at lower concentrations (10^-7 – 10^-6 M) acted as a weak stimulator of analyzed biochemical compounds in algal cells. No statistically significant effect was detected with the application of sodium amidotrizoate at a concentration of 10^-8 M. It seems that sodium amidotrizoate plays an important role in algal growth and development and probably possesses anti-auxin activity, like TIBA.

8

Sacharydy i polisacharydy w przetwórstwie mięsa

Cegiełka A.

Przemysł Spożywczy

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2008

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T. 62, nr 3

22-25

PL

W artykule przedstawiono znaczenie mono- i disacharydów, skrobi i jej pochodnych oraz nieskrobiowych hydrokoloidów polisacharydowych w przetwórstwie mięsa. Omówiono właściwości funkcjonalne tych substancji jako dodatków do żywności i korzyści wynikające z ich stosowania w przemyśle mięsnym.

EN

In the article, functions of mono- and disaccharides, starch, starch preparations and non-starch polysaccharide hydrocolloids, are presented. The most important functional properties of those substances as food additives as well as the potential benefits of their use in meat processing are described there.

9

The influence of traumatic acid on the growth and metabolite content of the green alga Chlorella vulgaris

Pietryczuk A., Piotrowska A., Czerpak R.

Oceanological and Hydrobiological Studies

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2008

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Vol. 37, No.1

3-15

EN

The effect of exogenous traumatic acid, (2E)-dodecene-1,12-dioic acid (TA), at concentrations of 10-6 - 10-3 M on the growth and development of the unicellular green alga Chlorella vulgaris was examined over 7 days. TA plays an important role in algal growth and development. Treatment with 10-5 M TA resulted in the greatest increase in cell numbers, by 77%, chlorophyll a content, by 126%, chlorophyll b, by 45%, total carotenoids, by 65%, monosaccharides, by 111%, and water-soluble proteins, by 37%, in relation to the control. After three days of treatment with 10-5 M TA cultures were analysed by SDS-PAGE, which showed the presence of new polypeptides with molecular weights 13-103 kDa.

10

Content of monosaccharides depending on the amount of nitrogen fertilization in various cultivars of Lolium multiflorum L. and Poa pratensis L.

Grygierzec B.

Ecological Chemistry and Engineering. A

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2008

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Vol. 15, nr 9

915-919

EN

The research was conducted in 2005-2006 at the Plant Breeding Station in Skrzeszowice near Krakow (220 m a.s.l.). The experiment, set up with a randomized block design in four replications, was used for hay-making and cut three times during the growing season. The studies considered three Lolium multiflorum cultivars (Atos, Gaza and Tur) and three cultivars of Poa pratensjs (Duna, Skiz and Slezanka). The experiment aimed to assess the cultivars of selected grass species with respect to their monosaccharide concentrations depending on the amount of applied nitrogen fertilization (90, 120 and 150 kg' ha-l). Lolium multiflorum cultivars revealed an about twice higher mean weighed content of monosaccharides in comparison with Poa pratensis. Tetraploid Lolium multiflorum cultivars (Atos and Gaza) bad between 9 and 31 % higher sugar concentrations than the diploid Tur cultivar. The highest content of water soluble carbohydrates was assessed in plants fertilized with the lowest dose of nitrogen (Gaza cv. - 171.3 g . kg-l d.m. and Skiz c. v. - 82.6 g . kg-l d.m.). The lowest content of the analyzed components was determined in plants as a result of treatment with 150 kg . ha-l nitrogen dose (Tur C.V. - 56.5 g . kg-l d.m. and Duna C.V. - 40.2 g . kg-l d.m.).

PL

Badania przeprowadzono w latach 2005-2006 w Stacji Hodowli Roślin w Skrzeszowicach koło Krakowa (220 m n.p.m.). Doświadczenie założone metodą losowanych bloków w czterech powtórzeniach użytkowano kośnie, stosując 3-krotne koszenie w sezonie wegetacyjnym. W badaniach uwzględniono trzy odmiany Lolium multiflorum L (Atos, Gaza, Tur) oraz trzy odmiany Poa pratensis L (Duna, Siz, Slezanka). Badania miały na celu ocenę odmian wybranych gatunków traw pod względem zawartości cukrów prostych w zależności od ilości zastosowanego nawożenia azotowego (90, 120 i 150 kg . ha-l). Odmiany Lolium multiflorum L odznaczały się około dwukrotnie większą średnią ważoną zawartością cukrów prostych w porównaniu do odmian Poa pratensis L. Odmiany tetraploidalne Lolium multiflorum L (Atos, Gaza) zawierały od 9 do 31 % więcej cukrów niż odmiana diploidalna Tur. Największą zawartość węglowodanów rozpuszczalnych w wodzie oznaczono w roślinach nawożonych najmniejszą dawką azotu (odmiana Gaza-171,3 g' kg s.m. i odmiana Skiz- 82,6 g' kg s.m.). Najniższą zawartość analizowanych składników stwierdzono u roślin pod wpływem nawożenia dawką azotu 150 kg . ha-I (odmiana Tur - 56,5 g . kg s.m. i odmiana Duna - 40,2 g . kg s.m.).

11

Monosaccharides in the water of the Gulf of Gdańsk

Grzybowski W., Maksymiuk A.

Oceanologia

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2001

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No. 43 (2)

247-256

EN

The concentration of monosaccharides in samples collected in the Gulf of Gdansk area was determined in water filtered through ~0.8 žm pore size filters. Seawater concentrations ranged from about 0.2 to 1.1 mg C dm-3, the highest values being detected at the mouth of the river Vistula. Seasonality was detectable in the data distribution; the majority of autumn values lay within the 0.2–0.4 range while concentrations in the spring samples were higher and the values more widely scattered. Measurements of monosaccharide concentrations at selected points during the whole observation period showed that values increased from spring to autumn as much as 5-fold. Concomitant analyses in Vistula river water yielded concentrations from 0.4 to 1.2 mg C dm-3. These latter values were all higher than those recorded in seawater in the corresponding months.