Instytut Chemii Bioorganicznej Polskiej Akademii Nauk

Instytut Chemii Bioorganicznej Pan

The United States of America, As Represented by the Secretary, Department of Health and Human Services

Fundacja Uniwersytetu Im. Adama Mickiewicza W Poznaniu

Marcin Krzysztof Chmielewski

Jan Barciszewski

Eliza Wyszko

Ewelina Adamska

Maria Markiewicz

Wojciech T Markiewicz

Serge L Beaucage

Hieronim Maciejewski

Katarzyna Rolle

Joanna Romanowska

Grzegorz Hreczycho

Sylwia Maria Musial

Beata Plitta

Malgorzata Giel-Pietraszuk

Wojciech Tadeusz Markiewicz

Agnieszka Fedoruk-Wyszomirska

Tadeusz Kulinski

Monika Nowak

Hieronim Franciszek Maciejewski

The subject of the invention is a new method of the synthesis of polyphosphate analogs, such as nucleosides, oligonucleotides, carbohydrates, peptides and proteins, which are of biological importance and are used in organic chemistry, molecular biology and biotechnology. Polyphosphate analogs, including in particular nucleoside 5'-triphosphates, display high biological activity and are responsible for the provision and storage of energy in live organisms. The method relates to the synthesis of organic polyphosphates of general formula (1), where n has a value of 0 to 2, while X stands for an organic radical, in particular nucleoside, oligonucleotide, peptide-carbohydrate or a protein radical. 

Method of polyphosphate synthesis

A novel method of simultaneously protecting two functions which are same or different, namely hydroxyl, amine, or thiol ones, particularly in sugars, polyalcohols, nucleosides, nucleotides, peptides, and nucleic acids during an organic synthesis, and to novel compounds for implementing this method, as well as to the method of obtaining these compounds. Method of simultaneously protecting two hydroxyl, amine, or thiol functions according to the invention by carrying out a protecting reaction between a compound having at least two free hydroxyl, amine, or thiol groups, and the disilane of formula 1, where R stands for Cl or Br, or I, or a substituent of formula 2, where X, X, X, Xare the same or different.

Method for protecting hydroxyl or amine or thiol functions, novel compounds with protected hydroxyl or amine or thiol groups, as well novel compounds for the implementation of this method

A cytosine analog, a method of preparation of a cytosine analog, a DNA methyltransferase 1 inhibitor, and a method for DNA methylation inhibition, is provided for the treatment of diseases associated with deviations from normal DNA methylation. The analog of cytosine may be comprised of 1, N, 5 and 6-substituted derivatives of cytosine or 5,6-dihydrocytosine, wherein the analog can be described by the chemical formula  where Ris H, R, R, 2'-deoxyribosyl, Ris alkyl or aryl, X is N or C, wherein if X in the analog of formula I is N, then Ris no substituent and if X in the analog of formula I and/or II is C or if X in the analog of formula II is N, then Rand Rare independently alkyl, aryl, hydroxyalkyl, aminoalkyl, hydroxyl, carboxyl, amino group, alkoxyl, aryloxyl, aminoalkyl, aminoaryl, thio group, sulfonyl, sulfinyl or halogen.

Cytosine analogue, a method of preparation of a cytosine analogue, a DNA methyltransferase 1 inhibitor, a method for DNA methylation inhibition, the use of the analogue in the treatment of diseases associated with deviations from normal DNA methylation

A procedure for using thermolabile groups to protect a hydroxyl function, above all in nucleosides, nucleotides, oligomers, nucleic acids during the reactions of organic synthesis. Various new compounds that can be used to implement the procedure. The way of using thermolabile groups to protect hydroxyl functions consists in a primary, secondary and tertiary hydroxyl group converting into a groups during the reaction between a compound and a compound whose hydroxyl group is to be blocked. The blocking reaction is carried out by means of widely known methods appropriate for that purpose in the presence of a chemically basic catalyst. The obtained product has its hydroxyl group blocked. Then the compound with the group blocked can be used for the purposes of various chemical processes. After their completion, the hydroxyl group is unblocked by dissolving it in a solvent at a temperature of 50-95&#xb0; C.

Way of using thermolabile groups to protect hydroxyl functions and compounds for implementing the procedure

The subjects of the present invention are the method of preparation of 4-furfurylcytosine and/or its derivatives, its use in the manufacture of anti-aging compositions and an anti-aging composition. As 4-furfurylcytosine and/or its derivatives possesses a series of biological properties it might be use as a composition having excellent anti-aging effect to prevent the sagging of skin and loss of luster and to improve sufficiently its aesthetic appearance without significantly change the growth rate and the total growth ability of the skin. Optimal methods of manufacturing this compound, while at the same time obtaining the highest possible process efficiency, with particular emphasis on its utility in the pharmaceutical and cosmetic industries are presented.

Method of obtaining of 4-N-furfurylcytosine and/or its derivatives, an anti-aging composition and use of 4-N-furfurylcytosine and/or its derivatives in the manufacture of anti-aging composition

Provided is a hydroxyl-protected alcohol comprising a thermolabile hydroxyl-protecting group comprising a 2-pyridyl substituent and a precursor of the thermolabile hydroxyl-protected alcohol. An exemplary thermolabile hydroxyl-protected alcohol is represented by the formula Pg-O&#x2014;R, wherein Pg is a protecting group of the formula: (Formula) wherein: A is a 2-pyridyl; Z is CHor NR; R, R, R, Rand Rare the same or different and each can be, e.g., H, alkyl, or alkyl comprising an aryl substituent; W is CO, CS, or SO; and R is the organic residue of the hydroxyl-protected alcohol. Also provided is a method of producing an alcohol, which method comprises heating the hydroxyl-protected alcohol, which optionally may be obtained from a precursor, at a temperature effective to cleave the hydroxyl-protecting group. The method can be used to produce oligonucleotides. 

Thermolabile hydroxyl protecting groups and methods of use

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Poznań, Poland

Marcin Krzysztof Chmielewski