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Mechanistic evidence for a front-side, SNi-type reaction in a retaining glycosyltransferase.

Abstract:

A previously determined crystal structure of the ternary complex of trehalose-6-phosphate synthase identified a putative transition state-like arrangement based on validoxylamine A 6'-O-phosphate and uridine diphosphate in the active site. Here linear free energy relationships confirm that these inhibitors are synergistic transition state mimics, supporting front-face nucleophilic attack involving hydrogen bonding between leaving group and nucleophile. Kinetic isotope effects indicate a highl...

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Publication status:
Published

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Publisher copy:
10.1038/nchembio.628

Authors


Davies, GJ More by this author
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Journal:
Nature chemical biology
Volume:
7
Issue:
9
Pages:
631-638
Publication date:
2011-09-05
DOI:
EISSN:
1552-4469
ISSN:
1552-4450
URN:
uuid:dc128fca-f331-4686-81ba-9ad54800e838
Source identifiers:
170197
Local pid:
pubs:170197

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