O -acetylserine

Structural formula
General
Surname	O -acetylserine
other names	O -acetyl- L -serine; (2 S ) -3-acetyloxy-2-aminopropanoic acid;
Molecular formula	C 5 H 9 NO 4
Brief description	white crystalline powder
External identifiers / databases
PubChem	99478
ChemSpider	89874
DrugBank	DB01837
Wikidata	Q309897
properties
Molar mass	147.13 g · mol -1
Physical state	firmly
solubility	soluble in methanol
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

The chemical compound O -acetylserine (OAS) is a naturally occurring, non-proteinogenic amino acid . It plays a role in bacteria and plants as a starting substance for the synthesis of cysteine and as a sensor for the availability of reduced sulfur .

biochemistry

The synthesis of O -acetylserine is catalyzed by serine acetyltransferases , with L - serine being acetylated with acetyl-coenzyme A as a cofactor on the hydroxyl group . By O lyases -Acetylserin (thiol) are O -Acetylserin and hydrogen sulfide with elimination of acetate to cysteine implemented.

Signal character

In the event of a sulfur deficiency, the O- acetylserine that is not converted into cysteine accumulates and can then serve as a signal substance in plants for this same sulfur deficiency. As a result, the expression of genes for sulfur assimilation is increased. In particular, O -acetylserine also regulates its own formation, since it leads to the dissociation of the cysteine synthase complex formed from serine acetyltransferase and O -acetylserine (thiol) lyase. Since serine acetyltransferases are only active in this complex, the synthesis of O -acetylserine is slowed down.

Individual evidence

↑ ^a ^b O-Acetyl-L-serine (mpbio)
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ Anna Feldman Salit, Markus Wirtz, Ruediger Hell, Rebecca C. Wade1: A Mechanistic Model of the cysteines Synthase Complex . In: Journal of Molecular Biology . tape 386 , 2009, p. 37-59 (English).
↑ Hankuil Yi, Ashley Galant, Geoffrey E. Ravilious, Mary L. Preuss, Joseph M. Jez: Sensing Sulfur Conditions: Simple to Complex Protein Regulatory Mechanisms in Plant Thiol Metabolism . In: Molecular Plant . tape 3 , no. 2 , 2010, p. 269-279 (English).

Web links

Entry for O-Acetylserine in the Human Metabolome Database (HMDB) , accessed September 24, 2013.

[mpbio-1] O-Acetyl-L-serine (mpbio)

[NV-2] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[Feldman-Salit-3] Anna Feldman Salit, Markus Wirtz, Ruediger Hell, Rebecca C. Wade1: A Mechanistic Model of the cysteines Synthase Complex . In: Journal of Molecular Biology . tape 386 , 2009, p. 37-59 (English).

[4] Hankuil Yi, Ashley Galant, Geoffrey E. Ravilious, Mary L. Preuss, Joseph M. Jez: Sensing Sulfur Conditions: Simple to Complex Protein Regulatory Mechanisms in Plant Thiol Metabolism . In: Molecular Plant . tape 3 , no. 2 , 2010, p. 269-279 (English).