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Author Hanes, Jeremiah W. ♦ Ealick, Steven E. ♦ Begley, Tadhg P.
Source CiteSeerX
Content type Text
File Format PDF
Subject Domain (in DDC) Computer science, information & general works ♦ Data processing & computer science
Subject Keyword Thiamin Phosphate Synthase ♦ Pyrimidine Carbocation Formation ♦ Thiamin Pyrophosphate ♦ Organic Chemist ♦ Active Form ♦ Thiamin Phosphate Biosynthesis ♦ Prenyl Transfer ♦ Wide Variety ♦ Glycosyl Transfer Reaction ♦ Biochemical Data ♦ Porphyrin Biosynthesis ♦ Cyclization Reaction ♦ Thiazole Pyrimidine ♦ Reactive Intermediate ♦ Several Enzyme-catalyzed Reaction ♦ Dissociative Mechanism ♦ Terpene Biosynthesis ♦ Vitamin B1 ♦ Penultimate Step ♦ Pyrrole Tetramerization
Abstract Carbocations have fascinated organic chemists for almost a century, and the properties of this reactive intermediate have been thoroughly studied.1 Carbocations have been proposed as intermedi-ates in several enzyme-catalyzed reactions, such as the prenyl transfer and cyclization reactions involved in terpene biosynthesis,2,3 the pyrrole tetramerization involved in porphyrin biosynthesis,4 the glycosyl transfer reactions involved in a wide variety of glycosyl-ations,5 and, the topic of this communication, the thiazole/pyrimidine coupling reaction involved in thiamin phosphate biosynthesis.6 This reaction, catalyzed by thiamin phosphate synthase (TP-synthase), is the penultimate step in the biosynthesis of thiamin pyrophosphate, the active form of vitamin B1. All organisms that synthesize thiamin pyrophosphate have some form of this coupling enzyme. Previous structural and biochemical data suggest a dissociative mechanism for TP-synthase (Scheme 1).6-8 Here we describe a study which
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