Surprising bacterial nucleotidyltransferase selectivity in the conversion of carbaglucose-1-phosphate.

Surprising bacterial nucleotidyltransferase selectivity in the conversion of carbaglucose-1-phosphate. Research Abstract Details 

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Surprising bacterial nucleotidyltransferase selectivity in the conversion of carbaglucose-1-phosphate. Abstract Text:

Kwang-Seuk Ko,Corbin J Zea,Nicola L Pohl,

The drive to understand the molecular determinants of carbohydrate binding as well as the search for more chemically and biochemically stable sugar derivatives and carbohydrate-based therapeutics has led to the synthesis of a variety of analogues that replace the glycosidic oxygen with sulfur or carbon. In contrast, the effect of substitution of the ring oxygen on the conformations and enzymatic tolerance of sugars has been largely neglected, in part because of the difficulty in obtaining these analogues. Herein we report the first synthesis of the carbocyclic version of the most common naturally occurring sugar-1-phosphate, glucose-1-phosphate, and its evaluation with bacterial and eukaryotic sugar nucleotidyltransferases. In contrast to results with the eukaryotic enzyme, the carbaglucose-1-phosphate serves as a substrate for the bacterial enzyme to provide the carbocyclic uridinediphosphoglucose. This result demonstrates the first chemoenzymatic strategy to this class of glycosyltransferase inhibitors and stable activated sugar mimics for cocrystallization with glycosyltransferases and their glycosyl acceptors. This difference in turnover between enzymes also suggests the possibility of using sugar nucleotidyltransferases in vivo to convert prodrug forms of glycosyltransferase inhibitors. In addition, we report several microwave-assisted reactions, including a five minute Ferrier rearrangement with palladium, that accelerate the synthesis of carbocyclic sugars for further studies.

Surprising bacterial nucleotidyltransferase selectivity in the conversion of carbaglucose-1-phosphate. Publishing Authors By Initials

KS Ko,CJ Zea,NL Pohl,

For similar enzymes and coenzymes: enzymes: transferases: phosphotransferases: nucleotidyltransferases research abstracts see: enzymes and coenzymes: enzymes: transferases: phosphotransferases: nucleotidyltransferases research

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Surprising bacterial nucleotidyltransferase selectivity in the conversion of carbaglucose-1-phosphate. Journal Published:

PUBLICATION TYPE: Research Support, U.S. Gov't,

Journal: Journal of the American Chemical Society

VOLUME: 126

Page Numbers: 13188-9

Journal Abbreviation: J. Am. Chem. Soc.

ISSN: 0002-7863

DAY: 20

MONTH: Oct

YEAR: 2004

Surprising bacterial nucleotidyltransferase selectivity in the conversion of carbaglucose-1-phosphate. Information

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LANGUAGE: eng

NlmUniqueID: 7503056

Surprising bacterial nucleotidyltransferase selectivity in the conversion of carbaglucose-1-phosphate. Keywords Mesh Terms:

KEYWORDS: Nucleotidyltransferases

MESH TERMS: metabolism

Chemical & Substance for Abstract: Surprising bacterial nucleotidyltransferase selectivity in the conversion of carbaglucose-1-phosphate. Information

Substance Name: Nucleotidyltransferases

Registry Number: EC 2.7.7.-

Grant and Affiliation Information for Surprising bacterial nucleotidyltransferase selectivity in the conversion of carbaglucose-1-phosphate.

AFFILIATION: Department of Chemistry and the Plant Sciences Institute, Gilman Hall, Iowa State University, Ames, Iowa 50011-3111, USA.

Country: United States

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MEDLINETA: J Am Chem Soc

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