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Articles on Cyclitols
Free cyclitol, soluble carbohydrate and protein contents in Vigna unguiculata and Phaseolus vulgaris bean sprouts.
We investigate the levels of inositols (myo-inositol, D-pinitol and ononitol), soluble carbohydrates and proteins in cotyledons of Phaseolus vulgaris and Vigna unguiculata sprouts. Sprouting increased myo-inositol and glucose content and reduction of raffinose and ononitol was observed. The protein...
Structural basis of alpha-fucosidase inhibition by iminocyclitols with K(i) values in the micro- to picomolar range.
Concise synthesis of iminocyclitols via Petasis-type aminocyclization.
A two-step method has been developed to synthesize several biologically important iminocyclitols in ca. 44-60% yields by using Petasis-type condensation. The method is very general and operationally simple, affording a series of iminocyclitols from easily available sugar derivatives. Unexpected dias...
Investigation of steric and functionality limits in the enzymatic dihydroxylation of benzoate esters. Versatile intermediates for the synthe...
A series of benzoate esters (methyl, ethyl, n-Pr, i-Pr, n-Bu, t-Bu, allyl, and propargyl) were subjected to enzymatic dihydroxylation by E. coli JM 109(pDTG 601) strain in a whole-cell fermentation. The cis-cyclohexadienediols were obtained in yields of approximately 1g/L except for...
Progress in aminocyclitol biosynthesis.
A stream of genetic and biochemical information available for the biosynthesis of aminocyclitols over the past few years has provided the foundation to study the modes of formation of this clinically important class of natural products. In addition to work on the identification and functional analys...
The gac-gene cluster for the production of acarbose from Streptomyces glaucescens GLA.O—Identification, isolation and characterization
We have identified a second acarbose production cluster using a genomic cosmid gene bank from Streptomyces glaucescens GLA.O and sequenced a region (42658bp; accession AM409314) which clearly contained a gene cluster (gac-cluster) for the synthesis of acarbose or acarbose related endproducts. The ga...
Enantiospecific synthesis and insect feeding activity of sulfur-containing cyclitols
The first syntheses of two deoxythiocyanocyclitols (4-deoxy-4-thiocyano-L-chiro-inositol and deoxythiocyanoconduritol F) and two deoxysulfonylcyclitol acetals are reported by a chemoenzymatic enantioselective route. The compounds were prepared by a sequence of enzymatic and ruthenium-catalyzed dihyd...
A two-directional approach to enantiopure 1,4-difluoro-cyclohexenes: synthesis of difluorinated cyclitol analogues.
A convenient synthesis of orthogonally protected 2-deoxystreptamine (2-DOS) as an aminocyclitol scaffold for the development of novel aminog...
We describe here a rapid and facile access to orthogonally protected 2-deoxystreptamine (2-DOS), a meso-diaminocyclitol known to be a pivotal component of most active aminoglycosides. Our synthetic approach started from highly protected methyl alpha-D-glucopyranoside which in turn was converted by a...
Use of enantiomerically pure 7-azabicyclo[2.2.1]heptan-2-ol as a chiral template for the synthesis of aminocyclitols.