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Formaldehyde and its adducts are ubiquitous in nature. Food may contain formaldehyde at levels 1–100 mg/kg. [ 24 ] Formaldehyde, formed in the metabolism of the amino acids serine and threonine , is found in the bloodstream of humans and other primates at concentrations of approximately 50 micromolar . [ 25 ]
In organic chemistry, the Mannich reaction is a three-component organic reaction that involves the amino alkylation of an acidic proton next to a carbonyl (C=O) functional group by formaldehyde (H−CHO) and a primary or secondary amine (−NH 2) or ammonia (NH 3). [1] The final product is a β-amino-carbonyl compound also known as a Mannich base.
Unlike other crosslinking agents, aldehyde-induced crosslinking is an intrinsically reversible process. NMR structure of these types of agents as interstrand crosslinks show that a 5'-GC adduct results in minor distortion to DNA, however a 5'-CG adduct destabilizes the helix and induces a bend and twist in the DNA. [14]
A Mannich base is a beta-amino-ketone, which is formed in the reaction of an amine, formaldehyde (or an aldehyde) and a carbon acid. [1] The Mannich base is an endproduct in the Mannich reaction, which is nucleophilic addition reaction of a non-enolizable aldehyde and any primary or secondary amine to produce resonance stabilized imine (iminium ion or imine salt).
A metabolite of benzopyrene forms an intercalated DNA adduct, at center. In molecular genetics, a DNA adduct is a segment of DNA bound to a cancer-causing chemical. This process could lead to the development of cancerous cells, or carcinogenesis. DNA adducts in scientific experiments are used as biomarkers of exposure.
Interestingly, many of these types of adducts are seen in urine from healthy humans, using urinary NA adductomics. [6] Confirmation of the presence of DNA-RNA crosslinks in urine came from a recent study that demonstrated the presence of cellular DNA-RNA crosslinks, arising from formaldehyde exposure. [13]
The Baylis–Hillman adducts and their derivatives have been extensively utilized for the generation of heterocycles and other cyclic frameworks. [40] MBH reactions are widely used in organic synthesis. For example, this reaction was used to construct key cyclic intermediates for syntheses of salinosporamide A, diversonol, and anatoxin-a. [41 ...
The formose reaction is of importance to the question of the origin of life, as it leads from simple formaldehyde to complex sugars like ribose, a building block of RNA.In one experiment simulating early Earth conditions, pentoses formed from mixtures of formaldehyde, glyceraldehyde, and borate minerals such as colemanite (Ca 2 B 6 O 11 5H 2 O) or kernite (Na 2 B 4 O 7). [6]