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Filtering by: Creator Lee, Jae Yeon License Attribution 3.0 United States

Catalyst selective and regiodivergent O- to C- or N-carboxyl transfer of pyrazolyl carbonates: synthetic and computational studies

Creator:

Gould, Eoin, Walden, Daniel M., Kasten, Kevin, Johnston, Ryne C., Wu, Jiufeng, Slawin, Alexandra M., Mustard, Thomas J. L., Johnston, Brittany, Davies, Tony, Cheong, Paul Ha-Yeon, and Smith, Andrew D.

Abstract:

The regiodivergent O- to C- or N-carboxyl transfer of pyrazolyl carbonates is described, with DMAP giving preferential N-carboxylation and triazolinylidenes promoting selective C-carboxylation (both with up to >99 : 1 regioselectivity). An enantioselective O- to C-carboxyl variant using NHC catalysis is demonstrated (up to 92% ee), while mechanistic and DFT studies outline...

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Article

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. Mustard,b Brittany Johnston,b Tony Davies,c Paul Ha-Yeon Cheong*b and Andrew D. Smith*a The
Mechanistic Insights into Validoxylamine A 7’-Phosphate Synthesis by VldE Using the Structure of the Entire Product Complex

Creator:

Cavalier, Michael C., Yim, Young-Sun, Asamizu, Shumpei, Neau, David, Almabruk, Khaled H., Mahmud, Taifo, and Lee, Yong-Hwan

Abstract:

The pseudo-glycosyltransferase VldE catalyzes non-glycosidic C-N coupling between an unsaturated cyclitol and a saturated aminocyclitol with the conservation of the stereochemical configuration of the substrates to form validoxylamine A 7'-phosphate, the biosynthetic precursor of the antibiotic validamycin A. To study the molecular basis of its mechanism, the three-dimensional structures of...

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Article

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Rep 24: 358–392. 12. Mahmud T, Lee S, Floss HG (2001) The biosynthesis of acarbose and validamycin

ScholarsArchive@OSU

Catalyst selective and regiodivergent O- to C- or N-carboxyl transfer of pyrazolyl carbonates: synthetic and computational studies

Mechanistic Insights into Validoxylamine A 7’-Phosphate Synthesis by VldE Using the Structure of the Entire Product Complex

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