A1 Refereed original research article in a scientific journal
Condensation of triformylmethane with guanosine
Authors: Koissi N, Neuvonen K, Munter T, Kronberg L, Lonnberg H
Publisher: MARCEL DEKKER INC
Publication year: 2001
Journal:: Nucleosides, Nucleotides and Nucleic Acids
Journal name in source: NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS
Journal acronym: NUCLEOS NUCLEOT NUCL
Volume: 20
Issue: 10-11
First page : 1761
Last page: 1774
Number of pages: 14
ISSN: 1525-7770
DOI: https://doi.org/10.1081/NCN-100107188
Abstract
Guanosine has been reacted with triformylmethane (TFM) in refluxing pyridine. Four different products, 4-7, were isolated by preparative RP-HPLC, and characterized by H-1 and C-13 NMR and UV spectroscopy and mass spectrometry. One of the products, the cyclic 1:1 adduct 4, is a stable cyclic carbinolamine formed probably by cyclization of the expected aminomethylene derivative 3. Compound 4 then undergoes reversible dehydration to the fully conjugated adduct 5. The appearance of the additional adducts, 6 and 7, suggests that TFM is prone to transformations resulting in the formation of methylenemalonaldehyde (9) and 1,1,3,3-tetraformylpropane (11).
Guanosine has been reacted with triformylmethane (TFM) in refluxing pyridine. Four different products, 4-7, were isolated by preparative RP-HPLC, and characterized by H-1 and C-13 NMR and UV spectroscopy and mass spectrometry. One of the products, the cyclic 1:1 adduct 4, is a stable cyclic carbinolamine formed probably by cyclization of the expected aminomethylene derivative 3. Compound 4 then undergoes reversible dehydration to the fully conjugated adduct 5. The appearance of the additional adducts, 6 and 7, suggests that TFM is prone to transformations resulting in the formation of methylenemalonaldehyde (9) and 1,1,3,3-tetraformylpropane (11).
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