Synthesis of 1,5-Anhydro-d-glycero-d-gluco-heptitol Derivatives as Potential Inhibitors of Bacterial Heptose Biosynthetic Pathways

Autor:	Vincent Gerusz, Paul Kosma, Dmytro Atamanyuk, Nuno M. Xavier, Markus Blaukopf
Rok vydání:	2017
Předmět:	chemistry.chemical_classification Phosphoramidite Anomer Glycal 010405 organic chemistry Stereochemistry Organic Chemistry Heptose Isomerase 010402 general chemistry 01 natural sciences Catalysis 0104 chemical sciences chemistry.chemical_compound chemistry Dihydroxylation Bromide Epimer
Zdroj:	Synthesis. 49:5320-5334
ISSN:	1437-210X 0039-7881
DOI:	10.1055/s-0036-1591518
Popis:	A series of 1,5-anhydro- d - glycero - d - gluco -heptitol derivatives have been prepared from 3- O -benzyl-1,2- O -isopropylidene- d - glycero - d - gluco -heptofuranose via conversion into anomeric bromide and thiophenyl derivatives, followed by glycal formation and reductive desulfurization, respectively. Global deprotection of the protected intermediates afforded the 1,5-anhydro derivatives of the d - glycero - d - gluco - and 1,2-dideoxy- d - altro - configuration as well as the 1,5-anhydro-2-deoxy- d - altro -hept-1-enitol. In addition, the 7- O -phosphorylated d - glycero - d - gluco -heptose and its 1,5-anhydro analogue were prepared in good yields utilizing phosphoramidite chemistry. A novel heptitol analogue based on a 1-deoxynojirimycin scaffold was also elaborated via a Wittig­-type chain elongation followed by dihydroxylation, separation of the resulting epimers, and global deprotection. The target compounds, however, were not active as inhibitors of the bacterial sedoheptulose-7-phosphate isomerase GmhA.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::8ae785713044b6b5e2dbf4e2e33a0d04 https://doi.org/10.1055/s-0036-1591518 Zobrazit plný text záznamu