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Glutaraldehyde is an organic compound with the formula (CH 2) 3 (CHO) 2.The molecule consists of a five carbon chain doubly terminated with formyl (CHO) groups. It is usually used as a solution in water, and such solutions exists as a collection of hydrates, cyclic derivatives, and condensation products, several of which interconvert.
Aldehyde structure. In organic chemistry, an aldehyde (/ ˈ æ l d ɪ h aɪ d /) is an organic compound containing a functional group with the structure R−CH=O. [1] The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl group.
The mechanism of the Mannich reaction starts with the formation of an iminium ion from the amine and formaldehyde. [4]: 140 The compound with the carbonyl functional group (in this case a ketone) will tautomerize to the enol form, after which it attacks the iminium ion.
It operates similarly to formaldehyde, causing the deformation of proteins' α-helices. However glutaraldehyde is a larger molecule than formaldehyde, and so permeates membranes more slowly. Consequently, glutaraldehyde fixation on thicker tissue samples can be difficult; this can be troubleshot by reducing the size of the tissue sample.
The reaction mechanism is related to that for the Reimer–Tiemann reaction, which uses chloroform as the formylating agent. [1] Protonated hexamine ring-opens to expose an iminium group. Addition to the aromatic ring results in an intermediate at the oxidation state of a benzylamine.
In broad strokes, the mechanism of the reaction is believed to first involve a Mannich-like addition of the alkynylmetal species into the iminium ion formed by condensation of the aldehyde and the secondary amine. This first part of the process is a so-called A 3 coupling reaction (A 3 stands for aldehyde-alkyne-amine).
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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]