Formylation

In preparative organic and technical chemistry, formylation is the introduction of the formyl group −CHO for the synthesis of aldehydes . In biochemistry, a partial step in peptide synthesis in eubacteria is known as N -terminal formylation.

Preparative chemistry

An example of a formylation reaction is Friedel-Crafts acylation :

With the only stable halide of formic acid - formyl fluoride (R = H; X = F) - or a gas mixture of carbon monoxide and a hydrohalic acid such as HF or HCl ( Gattermann-Koch reaction ), the reaction leads to an aldehyde. When using carboxylic acid halides of higher carboxylic acids (R is an organic radical, ≠ H), a ketone is formed . This reaction is generally called acylation .

Procedure

A number of processes have been developed for the formylation of suitable organic compounds (mostly aromatics ), some of which are also used on an industrial scale, including:

The aldehydes produced are used as such or serve as starting materials for further reactions.

biochemistry

In eubacteria, the N -formylation of a methionine unit is the first amino acid in bacterial protein synthesis (the N -terminus ). The enzyme involved before translation is Met-tRNAi transformylase (also methionine formyltransferase ) ( EC 2.1.2.9 ), which catalyzes the formylation of methionine tRNA . During translation , the formylation on the resulting protein is split off again by the peptide deformylase .

literature

Eberhard Breitmaier, Günther Jung: Organic chemistry. 5th edition, Georg Thieme Verlag, 2005, ISBN 3-13-541505-8

Individual evidence

↑ Entry on formylation. In: Römpp Online . Georg Thieme Verlag, accessed on June 7, 2014.
↑ D. Mazel, S. Pochet, P. Marlière: Genetic characterization of polypeptide deformylase, a distinctive enzyme of eubacterial translation. In: The EMBO journal. Volume 13, Number 4, February 1994, pp. 914-923, PMID 8112305 . PMC 394892 (free full text).
↑ KI Piatkov, TT Vu, CS Hwang, A. Varshavsky: Formyl-methionine as a degradation signal at the N-termini of bacterial proteins. In: Microbial Cell . Volume 2, number 10, 2015, pp. 376–393, doi : 10.15698 / mic2015.10.231 , PMID 26866044 , PMC 4745127 (free full text).

[1] Entry on formylation. In: Römpp Online . Georg Thieme Verlag, accessed on June 7, 2014.

[2] D. Mazel, S. Pochet, P. Marlière: Genetic characterization of polypeptide deformylase, a distinctive enzyme of eubacterial translation. In: The EMBO journal. Volume 13, Number 4, February 1994, pp. 914-923, PMID 8112305 . PMC 394892 (free full text).

[3] KI Piatkov, TT Vu, CS Hwang, A. Varshavsky: Formyl-methionine as a degradation signal at the N-termini of bacterial proteins. In: Microbial Cell . Volume 2, number 10, 2015, pp. 376–393, doi : 10.15698 / mic2015.10.231 , PMID 26866044 , PMC 4745127 (free full text).