93183-36-9Relevant articles and documents
Synthesis of a non-natural glucose-2-phosphate ester able to dupe the acc system of: Agrobacterium fabrum
Li, Si-Zhe,Vigouroux, Armelle,Ahmar, Mohammed,El Sahili, Abbas,Soulère, Laurent,Sago, La?la,Cornu, David,Moréra, Solange,Queneau, Yves
, p. 1090 - 1096 (2019)
The first non-natural derivative of the rare d-glucose-2-phosphate (G2P), namely glucose-2-(O-lactic acid phosphate) (G2LP), has been synthesized. When used as sole carbon source, G2LP enables bacterial growth of the plant pathogenic strain Agrobacterium fabrum C58 (formerly referred to as Agrobacterium tumefaciens). X-ray crystallography and affinity measurements investigations reveal that G2LP binds the periplasmic binding protein (PBP) AccA similarly to the natural compounds and with the same affinity. Moreover, enzymatic assays show that it is able to serve as substrate of the phosphodiesterase AccF. The properties found for G2LP demonstrate that the very unusual glucose-2-phosphoryl residue, present in G2LP, can be used as structural feature for designing non-natural systems fully compatible with the Acc cascade of A. fabrum.
The effectivity of 1H-triazoles and -tetrazoles as activators in acid-catalyzed phosphoramidite alcoholysis
Nurminen, Erkki J.,Mattinen, Jorma K.,Loennberg, Harri
, p. 2005 - 2008 (2007/10/03)
The efficiency of 5-nitro-1,2,4-1H-triazole (3), 5-(methylthio)-1H-tetrazole (4), and 5-(4-nitrophenyl)-1H-tetrazole (5) as activators in phosphoramidite alcoholysis has been studied relative to 1H-tetrazole (6). Reactions of these azoles with diisopropyl (diisopropylamido)phosphite (1a) were followed in THF, and the rates were found to increase with increasing acidity of the azoles. The Bronsted a value of 0.7 determined for this dependence is in agreement with data published earlier.
Application of the phosphoramidite-phosphite triester approach for the synthesis of combinations between oxygenated sterols and nucleoside analogues linked by phosphodiester bonds
Ji,Bannwarth,Luu
, p. 487 - 502 (2007/10/02)
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