75414-43-6Relevant articles and documents
FUNGAL ENZYMIC ACTIVITY DEGRADING 1,4-α-D-GLUCANS TO 1,5-D-ANHYDROFRUCTOSE
Baute, Marie-Antoinette,Baute, Robert,Deffieux, Gerard
, p. 3401 - 3404 (1988)
1,5-D-Anhydrofructose, the precursor of the antibiotic pyrone microthecin in morels and other fungi, is produced in Morchella vulgaris by a novel enzymic activity, presumably a lyasic one, which acts specifically on openchain 1,4-α-D-glucans; it can be prepared enzymatically in vitro from starch in 40 to 50percent yield.Key Word Index - Morchella vulgaris; M. costata; fungi; morels; cortacerone; mircothecin; carbohydrates; pyrones; glucosone; 1,5-D-anhydrofructose; bioconversion; 1,4-α-D-glucan; starch; glycogen.
Expedient conversion of d-glucose into 1,5-anhydro-d-fructose and into single stereogenic-center dihydropyranones, suitable six-carbon scaffolds for concise syntheses of the soft-coral constituents (-)-bissetone and (-)-palythazine
Brehm, Manfred,Goeckel, Volker H.,Jarglis, Pan,Lichtenthaler, Frieder W.
, p. 358 - 373 (2008/09/19)
High-yielding protocols are described to convert d-glucose-via hydroxylaminolysis of its hydroxyglucal esters, followed by deoximination and β-elimination of acid-into dihydropyranone building blocks with a single stereogenic center. Their versatility as enantiopure six-carbon scaffolds is highlighted by excellent regio- and stereocontrol in a variety of addition reactions and by their straightforward use as building blocks for the concise syntheses of the soft-coral constituents bissetone and palythazine in enantiopure form, thereby proving their absolute configuration. Moreover, several procedures are detailed to convert hydroxyglucal esters into 1,5-anhydro-d-fructose, their parent sugar, the direct low-temperature de-O-acylation being the most suitable for preparative purposes, as long as its access via enzymatic degradation of starch is not implemented on an appreciable scale.
1,5 AND 1,4-ANHYDROKETOSES, METHODS FOR THE PREPARATION OF 1,5-AND 1,4-ANHYDROKETOSES, INTERMEDIATES, AND USES OF 1,5-AND 1,4-ANHYDROKETOSES
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Page/Page column 75-76, (2008/06/13)
The present invention relates to 1,4- and 1,5-anhydro-D-ketoses (monosaccharides, oligosaccharides and various glycoconjugates), e.g. 1,5-anhydro-D-fructose. Moreover, the invention provides synthetic methods and novel intermediates and precursors suitable for their preparation. The methods include catalytic- and/or pyrolitic sulfenic acid elimination of corresponding ?-hydroxy sulfoxides, N-deprotection of N-substituted-aminoglycals, O-deprotection of carbohydrate enolethers and/or O-acyl-substituted carbohydrate enols, and regio- and stereoselective modification and subsequent chemical transformation of bicyclic and/or tricyclic 1,4- and 1,5-anhydro-glycoderivatives. Furthermore, the present invention provides novel applications of 1,4- and 1,5-anhydroketoses within pharmaceutical, food and cosmetic industries.