5699-41-2Relevant articles and documents
SYNTHESIS OF 2,2,6,6-TETRAMETHYL-4-DIAMINOALKYLPIPERIDIN-1-OXYLS
Bondarev, G. N.,Burzina, T. S.,Krasotskaya, G. I.,Kachurin, A. M.,Kleiner, A. R.
, p. 1700 - 1704 (1985)
-
Unexpected Acetylation of Endogenous Aliphatic Amines by Arylamine N-Acetyltransferase NAT2
Bergdahl, Ingvar A.,Conway, Louis P.,Correia, Mário S. P.,Globisch, Daniel,Rendo, Veronica,Sj?blom, Tobias
supporting information, p. 14342 - 14346 (2020/07/13)
N-Acetyltransferases play critical roles in the deactivation and clearance of xenobiotics, including clinical drugs. NAT2 has been classified as an arylamine N-acetyltransferase that mainly converts aromatic amines, hydroxylamines, and hydrazines. Herein, we demonstrate that the human arylamine N-acetyltransferase NAT2 also acetylates aliphatic endogenous amines. Metabolomic analysis and chemical synthesis revealed increased intracellular concentrations of mono- and diacetylated spermidine in human cell lines expressing the rapid compared to the slow acetylator NAT2 phenotype. The regioselective N8-acetylation of monoacetylated spermidine by NAT2 answers the long-standing question of the source of diacetylspermidine. We also identified selective acetylation of structurally diverse alkylamine-containing drugs by NAT2, which may contribute to variations in patient responses. The results demonstrate a previously unknown functionality and potential regulatory role for NAT2, and we suggest that this enzyme should be considered for re-classification.
Phenyl esters, preferred reagents for mono-acylation of polyamines in the presence of water
Pappas, Kyrie,Zhang, Xiang,Tang, Wei,Fang, Shiyue
body text, p. 5741 - 5743 (2009/12/06)
In the presence of water, several diamines and one triamine were mono-acylated at ambient to moderate temperatures using phenyl esters and a phenyl carbonate as acylation agents in good to excellent isolated yields. Both linear and cyclic polyamines were suitable substrates, and the acylating agents can be aryl and alkyl carboxylic acid esters.
Mono-acylation of symmetric diamines in the presence of water
Tang, Wei,Fang, Shiyue
supporting information; scheme or table, p. 6003 - 6006 (2009/04/11)
Simply reacting equal equivalents of symmetric diamines with esters or carbonates in the presence of a suitable amount of water gave mono-acylated products in good to quantitative yields.