Glucosamine and Glucosamine-6-phosphate Derivatives: Catalytic Cofactor Analogues for the glmS Ribozyme
نویسندگان
چکیده
منابع مشابه
Glucosamine metabolism. V. Enzymatic synthesis of glucosamine 6-phosphate.
Studies in viva on the biosynthesis of n-glucosamine, with the use of specifically labeled glucose in the rat (1,2) and in group A streptococci (3-5) showed that the glucose carbon chain was preserved during its conversion to the hexosamine. Leloir and Cardini (6, 7) noted that extracts obtained from Neurospora crassa converted glutamine and hexose phosphate to glutamic acid and a product tenta...
متن کاملPhosphatase-Inert Glucosamine 6-Phosphate Mimics Serve as Actuators of the glmS Riboswitch
The glmS riboswitch is unique among gene-regulating riboswitches and catalytic RNAs. This is because its own metabolite, glucosamine-6-phosphate (GlcN6P), binds to the riboswitch and catalytically participates in the RNA self-cleavage reaction, thereby providing a novel negative feedback mechanism. Given that a number of pathogens harbor the glmS riboswitch, artificial actuators of this potenti...
متن کاملStructure and catalytic mechanism of glucosamine 6-phosphate deaminase from Escherichia coli at 2.1 A resolution.
BACKGROUND Glucosamine 6-phosphate deaminase from Escherichia coli is an allosteric hexameric enzyme which catalyzes the reversible conversion of D-glucosamine 6-phosphate into D-fructose 6-phosphate and ammonium ion and is activated by N-acetyl-D-glucosamine 6-phosphate. Mechanistically, it belongs to the group of aldoseketose isomerases, but its reaction also accomplishes a simultaneous amina...
متن کاملGlucose-6-phosphate as a probe for the glucosamine-6-phosphate N-acetyltransferase Michaelis complex.
Glucosamine-6-phosphate N-acetyltransferase (GNA1) catalyses the N-acetylation of d-glucosamine-6-phosphate (GlcN-6P), using acetyl-CoA as an acetyl donor. The product GlcNAc-6P is an intermediate in the biosynthesis UDP-GlcNAc. GNA1 is part of the GCN5-related acetyl transferase family (GNATs), which employ a wide range of acceptor substrates. GNA1 has been genetically validated as an antifung...
متن کاملInhibition of Escherichia coli Glucosamine-6-phosphate Synthase by Reactive Intermediate Analogues
Glucosamine-6-phosphate synthase (GlmS) catalyzes the formation of D-glucosamine 6-phosphate from D-fructose 6-phosphate using L-glutamine as the ammonia source. Because N-acetylglucosamine is an essential building block of both bacterial cell walls and fungal cell wall chitin, the enzyme is a potential target for antibacterial and antifungal agents. The most potent carbohydrate-based inhibitor...
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ژورنال
عنوان ژورنال: The Journal of Organic Chemistry
سال: 2013
ISSN: 0022-3263,1520-6904
DOI: 10.1021/jo400192e