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Stereoselective synthesis of (+)-5-thiosucrose and (+)-5-thioisosucrose.
RSC Adv
March 2020
Kyoto Pharmaceutical University Misasagi, Yamashina Kyoto 607-8412 Japan
(+)-5-Thiosucrose 1, a novel isosteric sulfur analog of sucrose, was synthesized stereoselectively for the first time indirect β-d-fructofuranosidation involving selective β-d-psicofuranosidation, followed by stereo-inversion of the secondary hydroxy group at the C-3 position on the furanose ring. Glycosidation of protected 5-thio-d-glucose with a d-psicofuranosyl donor provided β-d-psicofuranosyl 5-thio-α-d-glucopyranoside and that with d-fructofuranosyl donor gave α-d-fructofuranosyl 5-thio-α-d-glucopyranoside. Two anomeric stereocenters of the glycosyl donor and acceptor were controlled correctly to provide a single disaccharide among four possible anomeric isomers in the glycosylation.
View Article and Find Full Text PDFCaudal hindbrain glucoprivation enhances gamma-aminobutyric acid release in discrete septopreoptic structures in the steroid-primed ovariectomized rat brain: role of mu opioid receptors.
Neuroendocrinology
March 2005
Department of Basic Pharmaceutical Sciences, School of Pharmacy, College of Health Sciences, University of Louisiana, Monroe, LA 71209, USA.
The neurochemical mechanisms underlying hindbrain glucoprivic suppression of the luteinizing hormone (LH) surge are not known. A body of experimental evidence supports the view that gonadal steroid positive-feedback action on the reproductive neuroendocrine axis relieves tonic GABAergic inhibition of gonadotropin-releasing hormone neurons by diminishing preoptic release of this neurotransmitter. The present studies evaluated the hypothesis that hindbrain glucoprivic attenuation of the LH surge may be correlated with site-specific modifications in gonadal steroid suppression of gamma-aminobutyric acid release in this region of the brain.
View Article and Find Full Text PDFSeptopreoptic mu opioid receptor mediation of hindbrain glucoprivic inhibition of reproductive neuroendocrine function in the female rat.
Endocrinology
November 2004
School of Pharmacy, 580 University Avenue, Monroe, Louisiana 71209, USA.
Central glucostasis is a critical monitored variable in neuroendocrine regulation of pituitary LH secretion. Glucoprivic signals originating within the caudal hindbrain suppress LH. Septopreoptic mu opioid receptors (mu-R) function within neural pathways maintaining basal LH levels and mediate the effects of diverse physiological stimuli on hormone release.
View Article and Find Full Text PDFEquilibrium and transient kinetic studies of the binding of cytochalasin B to the L-arabinose-H+ symport protein of Escherichia coli. Determination of the sugar binding specificity of the L-arabinose-H+ symporter.
Eur J Biochem
July 1993
Krebs Institute for Biomolecular Research, Department of Molecular Biology and Biotechnology, University of Sheffield, England.
The kinetics of the binding of cytochalasin B to the L-arabinose-H+ symport protein of Escherichia coli have been investigated, using a strain that over-produces the symport protein in the cytoplasmic membrane. Equilibrium binding studies revealed a single set of binding sites (2.9-8.
View Article and Find Full Text PDFCatabolite repressive effects of 5-thio-D-glucose on Saccharomyces cerevisiae.
J Gen Microbiol
December 1986
University Hospital of Iceland, Department of Pathology, Reykjavik.
The effect of the glucose analogue 5-thio-D-glucose (5TG) on the yeast Saccharomyces cerevisiae was studied. Derepression of mitochondrial respiratory chain cytochromes, alcohol dehydrogenase (isoenzyme II), NADH dehydrogenase and maltase was inhibited by 0.5-2 mM-5TG.
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