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1 article(s) from Lowary, Todd L

Studies on the substrate specificity of a GDP-mannose pyrophosphorylase from Salmonella enterica

Lu Zou,
Ruixiang Blake Zheng and
Todd L. Lowary

Beilstein J. Org. Chem. 2012, 8, 1219–1226, doi:10.3762/bjoc.8.136

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Graphical Abstract

Figure 1: (A) Conventional approach for the chemical synthesis of sugar nucleotides from sugar 1-phosphates; ...

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Figure 2: Structures of the Manp-1P derivatives (1–8) previously shown [24,25] to be substrates for S. enterica GDP-...

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Scheme 1: Reagents and conditions: (a) CH₃I, NaH, DMF, 80%; (b) Ac₂O–HOAc–H₂SO₄, 35:15:1, 81%; (c) EtSH, BF₃·...

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Scheme 2: Reagents and conditions: (a) CH₃I, NaH, DMF, 76%; (b) Ac₂O–HOAc–H₂SO₄, 35:15:1, 65%; (c) EtSH, BF₃·...

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Scheme 3: Reagents and conditions: (a) TrCl, DMAP, pyridine, 85%; (b) DMP, p-TsOH, 76%; (c) CH₃I, NaH, DMF, 9...

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Scheme 4: Reagents and conditions: (a) (i) NaOCH₃, CH₃OH; (ii) TBDPSCl, imidazole, DMF, 78%; (b) BnBr, NaH, T...

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Scheme 5: Reagents and conditions: (a) Ag₂O, CaSO₄, CH₃I, 52%; (b) Ac₂O–HOAc–H₂SO₄, 70:30:1, 96%; (c) EtSH, BF...

Jump to Scheme 5

Scheme 6: Reagents and conditions: (a) PPh₃, imidazole, I₂, 65%; (b) (i) Ac₂O–HOAc–H₂SO₄, 35:15:1; (ii) Pd–C,...

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Figure 3: Reaction catalyzed by GDP-ManPP.

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Figure 4: Structure of modified GDP-Man derivatives 48–52 produced from 9–13.

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Figure 5: Comparison of the relative activity of synthetic Manp-1P analogues 9–13 for GDP-ManPP, with that of...

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Figure 6: Summary of the substrate specificity of GDP-ManPP. Data from previous studies on the enzyme are als...

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Published 01 Aug 2012

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