Article

The synthesis of N-glycosyl phosphonamidates has been accomplished via the coupling of peracetylated glycosylamines with an appropriate phosphonochloridate in the presence of pyridine. The resulting glycosyl phosphonamidate esters are dealkylated with bromotrimethylsilane and then deacetylated to give the target compounds, which are potential transition-state analogue inhibitors of glycopeptidases and may prove useful as haptens for generating catalytic antibodies with glycopeptidase activity.Key words: enzyme inhibition, PNGase, phosphonamidate, amide hydrolysis.

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Faculty Opinions recommendation of L-Enantiomers of transition state analogue inhibitors bound to human purine nucleoside phosphorylase.

Faculty Opinions – Post-Publication Peer Review of the Biomedical Literature ◽

10.3410/f.1097544.553622 ◽

2008 ◽

Author(s):

Wayne Guida

Keyword(s):

Transition State ◽

Purine Nucleoside Phosphorylase ◽

Purine Nucleoside ◽

Nucleoside Phosphorylase ◽

Transition State Analogue ◽

Transition State Analogue Inhibitors

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A new class of C-nucleoside analogues. 1-(S)-aryl-1,4-dideoxy-1,4-imino-D-ribitols, transition state analogue inhibitors of nucleoside hydrolase

Tetrahedron Letters ◽

10.1016/s0040-4039(00)79290-2 ◽

1993 ◽

Vol 34 (45) ◽

pp. 7213-7216 ◽

Cited By ~ 51

Author(s):

Benjamin A. Horenstein ◽

Roger F. Zabinski ◽

Vern L. Schramm

Keyword(s):

Transition State ◽

Nucleoside Analogues ◽

New Class ◽

Nucleoside Hydrolase ◽

Transition State Analogue ◽

Transition State Analogue Inhibitors

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Transition State Analogue Inhibitors of 5′-Deoxyadenosine/5′-Methylthioadenosine Nucleosidase from Mycobacterium tuberculosis

Biochemistry ◽

10.1021/acs.biochem.7b00576 ◽

2017 ◽

Vol 56 (38) ◽

pp. 5090-5098 ◽

Cited By ~ 9

Author(s):

Hilda A. Namanja-Magliano ◽

Gary B. Evans ◽

Rajesh K. Harijan ◽

Peter C. Tyler ◽

Vern L. Schramm

Keyword(s):

Mycobacterium Tuberculosis ◽

Transition State ◽

Transition State Analogue ◽

Transition State Analogue Inhibitors

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DFT and Docking Study of Potential Transition State Analogue Inhibitors of Glycosyltransferases

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc20080591 ◽

2008 ◽

Vol 73 (5) ◽

pp. 591-607 ◽

Cited By ~ 4

Author(s):

Lucie Sihelniková ◽

Stanislav Kozmon ◽

Igor Tvaroška

Keyword(s):

Transition State ◽

Density Functional ◽

Density Functional Theory Method ◽

Docking Study ◽

Binding Mode ◽

Functional Theory ◽

Sulfate Anion ◽

Transition State Analogue ◽

Transition State Analogue Inhibitors ◽

Energy Maps

Conformational behavior of the [(2S,3R,4R,5S)-3,4,5-trihydroxy-2-(phenylsulfanyl)tetrahydrofuran-2-yl]methyl sulfate anion (2), which is the potential transition state (TS) analogue of the inverting glycosyltransferases, was studied by means of two-dimensional potential-energy maps, using a density functional theory method at the B3LYP/6-31+G* level. The maps revealed the presence of eight low-energy domains which were refined at the B3LYP/6-311++G** level and led to six conformers in vacuum. In aqueous solution, two conformers dominate at equilibrium. The preferred conformers superimpose well with the transition state structure, as determined previously for glycosyltransferase GnT-I. The conformations of 2 in the active site of glycosyltransferase GnT-I were obtained by docking methods. It was found that one of the two best docking poses mimics the binding mode of TS. These results suggest that the proposed TS mimics 2 have the potential to be used as a scaffold for the design of TS analogue inhibitors.

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