Topic
Glycal
About: Glycal is a research topic. Over the lifetime, 897 publications have been published within this topic receiving 17422 citations.
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TL;DR: The synthesis of a fluorinated analogue of ADP-L-glycero-beta-D-manno-heptopyranose, the donor substrate of the heptosyl transferase WaaC, which catalyzes the incorporation of this carbohydrate into LPS.
Abstract: Heptosides are found in important bacterial glycolipids such as lipopolysaccharide (LPS), the biosynthesis of which is targeted for the development of novel antibacterial agents. This work describes the synthesis of a fluorinated analogue of ADP-L-glycero-beta-D-manno-heptopyranose, the donor substrate of the heptosyl transferase WaaC, which catalyzes the incorporation of this carbohydrate into LPS. Synthetically, the key step for the preparation of ADP-2F-heptose is the simultaneous and stereoselective installation of both the fluorine atom at C-2 and the phosphoryl group at C-1 through a selectfluor-mediated (selectfluor=1-chloromethyl-4-fluorodiazoniabicyclo[2.2.2]octane bis(triflate)) electrophilic addition/nucleophilic substitution involving a heptosylglycal. Therefore, we detail in this article 1) the stereoselective preparation of the key intermediates heptosylglycals, 2) the development of a new fluorophosphorylation procedure allowing an excellent beta-gluco stereoselectivity with "all-equatorial" glycals, 3) the synthesis of the target ADP-2F-heptose, and 4) some comments on the contacts observed between the fluorine atom of the final molecule and the protein in the crystallographic structure of heptosyltransferase WaaC.
61 citations
61 citations
TL;DR: In this paper, an improved preparative method for homogeneous azidophenylselenylation of glycals is described consisting of reaction with TMSN 3 and Ph 2 Se 2 in the presence of PhI(OAc) 2.
59 citations
TL;DR: The stereoselectivity of d-glucal derivatives with PhSCl and PhSeCl is dependent on the presence of an electronegative heteroatom substituent and the nature of the functionality at C(4) as discussed by the authors.
57 citations
TL;DR: Reduction of glycals and didesoxy-2,3 hexeno-2pyranosides; application a la synthese du compose du titre a partir de di-O-acetyl rhamnal.
Abstract: Reduction de glycals et de didesoxy-2,3 hexeno-2pyranosides; application a la synthese du compose du titre a partir de di-O-acetyl rhamnal
56 citations