A myo-inositol dehydrogenase involved in aminocyclitol biosynthesis of hygromycin A

• Michael O. Akintubosun and
• Melanie A. Higgins

Beilstein J. Org. Chem. 2024, 20, 589–596, doi:10.3762/bjoc.20.51

• dehydrogenase (Figure 2a). We also found there was reduced activity with scyllo-inositol, minimal activity with ʟ-chiro-inositol and no activity with ᴅ-glucose, ᴅ-chiro-inositol, epi-inositol, muco-inositol, and allo-inositol. By comparison, other myo-inositol dehydrogenases typically do not have activity on

• scyllo-inositol but can have reduced activity on ᴅ-chiro-inositol, ᴅ-glucose, ᴅ-xylose and 4-O-benzyl-myo-inositol [12][13][15][16][17]. However, scyllo-inositol dehydrogenases are active on scyllo-inositol and myo-inositol to a lesser extent [16][18]. Altogether, this suggests that Hyg17 can accommodate

• different substrates when compared to known myo-inositol dehydrogenases and has a more similar substrate scope to scyllo-inositol dehydrogenases. We performed kinetics analysis for Hyg17 with myo- and scyllo-inositol (Table 1 and Figure 2d,e). The KM value for Hyg17 with myo-inositol was 9.0 ± 1.1 mM, which

Diastereoselective synthesis of new O-alkylated and C-branched inositols and their corresponding fluoro analogues

• Charlotte Collet,
• Françoise Chrétien,
• Yves Chapleur and
• Sandrine Lamandé-Langle

Beilstein J. Org. Chem. 2016, 12, 353–361, doi:10.3762/bjoc.12.39

• protein (Aβ), characteristic aggregation in Alzheimer disease (AD), and more specifically Aβ42 peptide allowing its conformational change and its stabilization into small, nonfibrillar complexes, less toxic for neuronal cells [20][21][22][23]. The most efficient representative, scyllo-inositol, was shown

• to be able to reduce plaque burden and to improve the performance on memory tasks in animal models of Alzheimer disease [24][25][26][27][28][29]. Scyllo-inositol was recently used in human clinical trials for the treatment of patients suffering from AD [30][31]. McLaurin has also demonstrated that

• the corresponding fluoroinositol (1-fluoro-1-deoxy-scyllo-inositol) was also a good candidate to limit this aggregation. However, in vivo studies in animal models of Alzheimer disease with 1-[18F]fluoro-1-deoxy-scyllo-inositol used as radiotracer for positron emission tomography (PET) have shown that

Design and synthesis of a cyclitol-derived scaffold with axial pyridyl appendages and its encapsulation of the silver(I) cation

• Pierre-Marc Léo,
• Christophe Morin and
• Christian Philouze

Beilstein J. Org. Chem. 2010, 6, 1022–1024, doi:10.3762/bjoc.6.115

• Pierre-Marc Leo Christophe Morin Christian Philouze Département de Chimie Moléculaire (CNRS, UMR 5250, ICMG FR-2607) Université Joseph Fourier, 301 Rue de la Chimie, 38402 Grenoble Cedex, France 10.3762/bjoc.6.115 Abstract Conversion of a myo-inositol derivative into a scyllo-inositol-derived

• scaffold with C3v symmetry bearing three axial pyridyl appendages is presented. This pre-organized hexadentate ligand allows complexation of silver(I). The crystal structure of the complex was established. Keywords: cyclitol; glyco-scaffolds; hexadentate; scyllo-inositol; silver(I) complexation

• -inositol the three axial hydroxy groups can be used to link substituents in a pre-organized manner [8][9][10]. Thus the introduction of pyridine groups (known to bind Ag(I) efficiently [11][12][13][14]) on a scyllo-inositol orthoester was considered, which led to the design of scaffold 1 (Figure 1). Indeed