607357-22-2Relevant academic research and scientific papers
On the way to glycoprocessing inhibitors - Synthesis of an imidazolo-nectrisine-phosphono acid derivative: A potential glycosyltranferase inhibitor
Tschamber, Theophile,Gessier, Francois,Neuburger, Markus,Gurcha, Sudagar S.,Besra, Gurdyal S.,Streith, Jacques
, p. 2792 - 2798 (2003)
Assuming the transition state of glycosyltransferase inhibitors to be similar to those encountered with potent glycosidase inhibitors - i.e. a flattened conformation with a positively charged anomeric centre - we worked out a synthesis of the D-arabino-configured phosphonic acid target molecule 2 derived from an imidazolo-sugar. The key synthetic intermediate is the linear imidazolo L-xylo compound 10 which could be obtained, either from L-threo precursor 6 by a coupling reaction with imidazole derivative 5, or from L-sorbose. A multi-step and site specific iodination of 10 gave the monoiodo-L-xylo derivative 14 which was cyclised to the D-arabino-configured bicyclic azasugar 15. Phosphorylation of the Grignard derivative of the latter, followed by mono-esterification with citronellol along with some protection-deprotection steps led to target molecule 2. The potential inhibitor 2 is supposed to be protonated at its most basic N atom by a carboxylic acid residue in the arabinosyl-transferase active site. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
