substituted adenines
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Author(s):  
I. S. Cherepanov ◽  
A. A. Kamasheva ◽  
E. I. Kashapova

In this work, potentially bioactive condensation products of adenine with D-mannose and 6-deoxy-L-mannose (L-rhamnose) were synthesized in water and ethanol solutions. According to FTIR spectroscopy and elemental analysis, mono-N6-glycosylated adenines were isolated from water systems in satisfactory yields, while ethanol solutions contained mixtures of N6 and N9-products, as well as complexes of the latter with copper ions. A detailed analysis of the vibrational spectra of N6-glycosyladenines confirmed the structure of carbohydrate fragments in the form of pyranose rings, while some part of the product was obtained in the form of deoxyaminoketosis. N-rhamnosyladenine was formed with a more than double yield because of a higher stability of rhamnose with regard to side reactions. The reflection spectra of model solutions of glycosyladenines, recorded 4 days after preparation, showed no bands characteristic of free adenine in the range of 1250-1110 cm-1, which indicates a sufficient resistance of the synthesized products towards hydrolytic cleavage under experimental conditions. The conducted biotesting of the isolated products on wheat seeds (Triticum aestivum L.) showed an increase in the content of chlorophylls in seedlings for both mannosilade-nines compared to the control. A decrease in the concentration of synthesized products in germination solutions from 0.1 to 0.001% led to an increase in the accumulation of photosynthetic pigments, while this effect was more pronounced for rhamnosyladenine. The latter can be connected with the structural features of car-bohydrate fragments, in particular, the differences in the hydroxylation degree of glucoside fragments. Future research will investigate the mechanisms of transformation and action of N6-substituted adenines.


2016 ◽  
Vol 40 (2) ◽  
pp. 1807-1816 ◽  
Author(s):  
Kalyanashis Jana ◽  
Bishwajit Ganguly

The modified adenine and thymine mispair achieves a remarkable stability, which can presumably help the DNA lesions to be less cytotoxic.


2015 ◽  
Vol 34 (1) ◽  
pp. 159 ◽  
Author(s):  
Valya Nikolova ◽  
Boris Galabov

<p><strong>Abstract:</strong><strong> </strong>The hydrogen bonding between substituted adenines and thymine was investigated by density functional theory computations at the B3LYP/6-311+G(2d,2p) level. The effect of 20 different polar substituents at position 8 in adenine was examined in detail. Three different theoretical parameters, reflecting the electrostatics at the atoms involved in hydrogen bonding, were applied. An excellent correlation between electrostatic potentials at the bonding atoms in the monomer adenines and interaction energies was derived (Eqn. 2). It can be employed in designing bioactive adenine derivatives that are able to bind with a finely adjusted strength to thymine bioreceptor sites. NBO and Hirshfeld atomic charges are found to be less successful as reactivity predictors in these interactions.</p>


ChemInform ◽  
2014 ◽  
Vol 46 (2) ◽  
pp. no-no
Author(s):  
M. E. Garcia-Rubino ◽  
M. C. Nunez-Carretero ◽  
D. Choquesillo-Lazarte ◽  
J. M. Garcia-Ruiz ◽  
Yolanda Madrid ◽  
...  

ChemInform ◽  
2014 ◽  
Vol 45 (15) ◽  
pp. no-no
Author(s):  
Nadia Senhoraes ◽  
A. Luisa Costa ◽  
Deolinda I. Silva ◽  
M. Fernanda Proenca ◽  
Alice M. Dias

RSC Advances ◽  
2014 ◽  
Vol 4 (43) ◽  
pp. 22425-22433 ◽  
Author(s):  
M. E. García-Rubiño ◽  
M. C. Núñez-Carretero ◽  
D. Choquesillo-Lazarte ◽  
J. M. García-Ruiz ◽  
Yolanda Madrid ◽  
...  

The Mitsunobu reaction under microwave-assisted conditions reveals a complete inversion of the stereogenic centre of the secondary alcohol giving an alkylated purine linked to a homochiral six-membered ring.


Tetrahedron ◽  
2013 ◽  
Vol 69 (47) ◽  
pp. 10014-10021 ◽  
Author(s):  
Nádia Senhorães ◽  
A. Luísa Costa ◽  
Deolinda I. Silva ◽  
M. Fernanda Proença ◽  
Alice M. Dias

2013 ◽  
Vol 127 ◽  
pp. 141-149 ◽  
Author(s):  
Alicia Domínguez-Martín ◽  
Ángel García-Raso ◽  
Catalina Cabot ◽  
Duane Choquesillo-Lazarte ◽  
Inmaculada Pérez-Toro ◽  
...  

ChemInform ◽  
2013 ◽  
Vol 44 (32) ◽  
pp. no-no
Author(s):  
Michal Maryska ◽  
Nadezda Chudikova ◽  
Vladislav Kotek ◽  
Dalimil Dvorak ◽  
Tomas Tobrman

2013 ◽  
Vol 144 (4) ◽  
pp. 501-507 ◽  
Author(s):  
Michal Maryška ◽  
Naděžda Chudíková ◽  
Vladislav Kotek ◽  
Dalimil Dvořák ◽  
Tomáš Tobrman

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