Condensation of triformylmethane with guanosine



: Koissi N, Neuvonen K, Munter T, Kronberg L, Lonnberg H

Publisher: MARCEL DEKKER INC

: 2001

Nucleosides, Nucleotides and Nucleic Acids

NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS

: NUCLEOS NUCLEOT NUCL

: 20

: 10-11

: 1761

: 1774

: 14

: 1525-7770

DOI: https://doi.org/10.1081/NCN-100107188


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).



Last updated on 2025-13-10 at 14:20