78880-62-3

Usage

InChI:InChI=1/C13H13N5O5/c19-4-6-8(20)9(21)12(23-6)18-5-15-7-10(18)16-13-14-2-1-3-17(13)11(7)22/h1-3,5-6,8-9,12,19-21H,4H2/t6-,8-,9-,12-/m1/s1

Upstream product

• 100815-31-4 5,6,7,8-tetrahydro-11-formyl-3(β-D-ribofuranosyl)-6,8-epoxyethenopyrimido<1,2-a>purin-10(3H)-one 
• 624-67-9 Propargylic aldehyde 
• 118-00-3 G 
• 542-78-9 Malondialdehyde 
• 122-31-6 malondialdehyde bis(diethyl acetal) 
• 78923-06-5 3t-methoxy-propenal 
• 24338-69-0 β-(benzoyloxy)acrolein 
• 86030-90-2 β-(p-nitrophenoxy)acrolein 

Downstream Products

• 542-78-9 Malondialdehyde 
• 118-00-3 G 
• 100815-31-4 5,6,7,8-tetrahydro-11-formyl-3(β-D-ribofuranosyl)-6,8-epoxyethenopyrimido<1,2-a>purin-10(3H)-one 

Relevant academic research and scientific papers

Reaction of Malonaldehyde with Nucleic Acid. I. Formation of Fluorescent Pyrimidopurin-10(3H)-one Nucleosides

The reactions of malonaldehyde with guanosine and 2'-deoxyguanosine proceed slowly under acidic conditions to give new pyrimidopurine nucleosides, 3a and 3b, respectively.These compounds emit strong yellow fluorescence and are hydrolyzed by NaOH into malonaldehyde and guanosine from 3a (2'-deoxyguanosine from 3b).From chemical and spectroscopic evidence, these compounds were deduced to be 3-β-D-ribofuranosylpyrimidopurin-10(3H)-one (3a) and 3-(2-deoxy-β-D-erythro-pentofuranosyl)pyrimidopurin-10(3H)-one (3b).No products were detected in the reaction mixture of malonaldehyde with 1-methylguanosine, adenosine, cytidine, uridine, thymidine, 2'-deoxyadenosine, or 2'-deoxycytidine.

Synthetic method and application of endogenous nucleoside M1dG and derivative thereof

The invention belongs to the field of chemical synthesis, and particularly discloses a synthesis method and application of endogenous nucleoside M1dG and derivatives thereof. The structural formula of the endogenous nucleoside M1dG and the derivative thereof is as follows: substituent groups on pentose are as follows: when R3 = H, R1 = R2 = acetoxy, benzoyloxy or hydroxyl; when R1 = R2 = R3, R1 = acetoxy, benzoyloxy or hydroxyl; when R2 = R3 = acetoxy, R1 is iodine, bromine, azido or thioacetyl; when R2 = R3 = hydroxyl, R1 is iodine, bromine, azido or sulfydryl; according to the synthesis, AcOH which is relatively friendly to the environment is used as a solvent, Ac2O is used as an additive, 1, 1, 3, 3-tetramethoxypropane is connected with an imino group on guanosine and cyclization is carried out, so that a series of endogenous nucleosides M1dG with novel structures and derivatives thereof are constructed. The method is simple and convenient in experimental process operation, high in yield and good in chemical selectivity, a series of endogenous nucleoside M1dG with novel structures and derivatives thereof can be efficiently constructed, and a new method and thought are provided for synthesis of the compounds.

STRUCTURE OF A NEW MODIFIED NUCLEOSIDE FORMED BY GUANOSINE-MALONALDEHYDE REACTION

A new modified nucleoside was formed by the reaction of guanosine with malonaldehyde under acidic condition.This compound emitted strong yellow fluorescence and was hydrolyzed by NaOH into guanosine and malonaldehyde.Its structure was determined to be 1,N2-(1-propenyl-3-ylidene)guanosine by the spectroscopic analysis.