110497-19-3Relevant academic research and scientific papers
Synthesis,in vitro anticancer evaluation, and interference with cell cycle progression of N-phosphoamino acid esters of zidovudine and stavudine
Wu,Xiao,Jiang,Fu,Ju,Zhao
, p. 1797 - 1811 (2004)
A series of N-diisopropylphosphoryl (DIPP) L-amino acid ester prodrugs of zidovudine (AZT) (3a-3e) and stavudine (d4T) (4a-4e) has been prepared. The activity of these compounds against MCF-7 cells (human pleural effusion breast adenocarcinoma cell line)
Synthesis of N-phosphopeptides coupled by dichlorotriphenyl-phosphorane
Dong,Fu,Zhao
, p. 2067 - 2075 (2001)
Coupling of N-phosphoamino acids 2 and amino acid methyl esters by dichlorotriphenylphosphorane 3 produced N-phosphopeptide methyl esters 5, which were sequentially hydrolyzed in triethylamine or dilute NaOH aqueous solution. The target products N-phospho
A practical preparation of diisopropyl phosphoryl protected amino acids
Brands,Wiedbrauk,Williams,Dolling,Reider
, p. 9583 - 9586 (1998)
N-Diisopropyl phosphoryl protected amino acids can be prepared in high yield and without racemization by slow addition of sodium hypochlorite to a solution of the amino acid and diisopropylphosphite in water while carefully maintaining a constant pH via t
Chiral Amplification of Phosphoramidates of Amines and Amino Acids in Water
Da?ková, Vanda,Buter, Jeffrey,Schoonen, Anne K.,Lutz, Martin,de Vries, Folkert,Feringa, Ben L.
supporting information, p. 11120 - 11126 (2021/04/09)
The origin of biomolecular homochirality continues to be one of the most fascinating aspects of prebiotic chemistry. Various amplification strategies for chiral compounds to enhance a small chiral preference have been reported, but none of these involves phosphorylation, one of nature's essential chemical reactions. Here we present a simple and robust concept of phosphorylation-based chiral amplification of amines and amino acids in water. By exploiting the difference in solubility of a racemic phosphoramidate and its enantiopure form, we achieved enantioenrichment in solution. Starting with near racemic, phenylethylamine-based phosphoramidates, ee's of up to 95 % are reached in a single amplification step. Particularly noteworthy is the enantioenrichment of phosphorylated amino acids and their derivatives, which might point to a potential role of phosphorus en-route to prebiotic homochirality.
An isotope (18O, 15N, and 2H) technique to investigate the metal ion interactions between the phosphoryl group and amino acid side chains by electrospray ionization mass spectrometry
Gao, Xiang,Hu, Xiaomei,Zhu, Jun,Zeng, Zhiping,Han, Daxiong,Tang, Guo,Huang, Xiantong,Xu, Pengxiang,Zhao, Yufen
scheme or table, p. 689 - 702 (2012/03/27)
Cationic metal ion-coordinated N-diisopropyloxyphosphoryl dipeptides (DIPP-dipeptides) were analyzed by electrospray ionization multistage tandem mass spectrometry (ESI-MSn). Two novel rearrangement reactions with hydroxyl oxygen or carbonyl ox
Structure-Activity Relationships of a Series of 2-Amino-4-thiazole-Containing Renin Inhibitors
Patt, William C.,Hamilton, Harriet W.,Taylor, Michael D.,Ryan, Michael J.,Taylor, David G.,et al.
, p. 2562 - 2572 (2007/10/02)
A series of renin inhibitors was synthesized that contained a 2-amino-4-thiazolyl moiety at the P2 position.These derivatives are potent inhibitors of monkey renin in vitro and are selective in that they only weakly inhibit the closely related
Synthesis of N-(Diisopropyloxyphosphoryl)amino Acids and Peptides
Ji, Gai-Jiao,Xue, Chu-Biao,Zeng, Jia-Ning,Li, Li-Pou,Chai, Wen-Gang,Zhao, Yu-Fen
, p. 444 - 448 (2007/10/02)
N-(Diisopropyloxyphosphoryl)amino acids (N-Dipp-amino acids) are prepared from diisopropyl phosphite and amino acids in mixed aqueous media in one step.They can be activated by dicyclohexylcarbodiimide or other activating agents for the synthesis of N-(di
