α-Fluorinated phosphonates as substrate mimics for glucose 6-phosphate dehydrogenase: The CHF stereochemistry matters

DB Berkowitz, M Bose, TJ Pfannenstiel…

Index: Berkowitz, David B.; Bose, Mohua; Pfannenstiel, Travis J.; Doukov, Tzanko Journal of Organic Chemistry, 2000 , vol. 65, # 15 p. 4498 - 4508

Full Text: HTML

Citation Number: 102

Abstract

Reported is a systematic study of the “fitness”(in terms of k cat/K m) of a series of phosphonate mimics of glucose 6-phosphate (G6P) as unnatural substrates for G6P dehydrogenase from Leuconostoc mesenteroides. The four G6P analogues (9, 10, 15a, and 15b) differ only in the degree of fluorination at the “bridging” phosphonate carbon. All have been synthesized from benzyl 6-O-trifluoromethanesulfonyl-2, 3, 4-tri-O-benzyl β-d- ...