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

• aminocyclitol moieties. The biosynthesis of the aminocyclitol has been proposed to proceed through six enzymatic steps from glucose 6-phosphate through myo-inositol to the final methylenedioxy-containing aminocyclitol. Although there is some in vivo evidence for this proposed pathway, biochemical support for

• the individual enzyme activities is lacking. In this study, we verify the activity for one enzyme in this pathway. We show that Hyg17 is a myo-inositol dehydrogenase that has a unique substrate scope when compared to other myo-inositol dehydrogenases. Furthermore, we analyze sequences from the protein

• family containing Hyg17 and discuss genome mining strategies that target this protein family to identify biosynthetic clusters for natural product discovery. Keywords: aminocyclitol; biosynthesis; hygromycin A; inositol dehydrogenase; myo-inositol; Introduction Hygromycin A is a natural product that

Synthesis of ether lipids: natural compounds and analogues

• Marco Antônio G. B. Gomes,
• Alicia Bauduin,
• Chloé Le Roux,
• Romain Fouinneteau,
• Wilfried Berthe,
• Mathieu Berchel,
• Hélène Couthon and
• Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2023, 19, 1299–1369, doi:10.3762/bjoc.19.96

• ) myo-inositol (20.6). The oxidation of the phosphite intermediate with m-CPBA followed by the catalytic hydrogenolysis of the benzyl protecting groups produced PIP3-PAF (20.7). 2 Edelfosine and diether analogues PAF and PAF-analogues that feature an acyl or more generally an ester group in sn-2

Lectins of Mycobacterium tuberculosis – rarely studied proteins

• Katharina Kolbe,
• Sri Kumar Veleti,
• Norbert Reiling and
• Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2019, 15, 1–15, doi:10.3762/bjoc.15.1

• of a phosphatidyl-myo-inositol core structure, glycosylated at the 2-position of myo-inositol [49][50][51]. The oligosaccharide of LM consists exclusively of linear (1→6)-linked and (1→2)-branched α-mannopyranosides [22], while in LAM the mannan structure is elongated by highly (1→2), (1→3) and (1→5

Useful access to enantiomerically pure protected inositols from carbohydrates: the aldohexos-5-uloses route

• Felicia D’Andrea,
• Giorgio Catelani,
• Lorenzo Guazzelli and
• Venerando Pistarà

Beilstein J. Org. Chem. 2016, 12, 2343–2350, doi:10.3762/bjoc.12.227

• followed by reduction with NaBH(OAc)3) represents the biomimetic synthesis of myo-inositol. Furthermore, the sugar-based pathway leads directly to enantiomerically pure selectively protected inositols and does not require any desymmetrisation procedure which is needed when myo-inositol and other achiral

• four are unnatural synthetic products (cis, epi, allo, and muco). Several myo-inositol phosphates, for instance D-myo-inositol-1,4,5-triphosphate [D-I(1,4,5)P3] and D-myo-inositol-1,3,4,5-tetrakisphosphate [D-I(1,3,4,5)P4], are ubiquitous in all living organisms. They are involved in different crucial

• development of practical and efficient synthetic methods for stereoselectively accessing all natural and unnatural inositols as well as their derivatives. There are three general synthetic approaches to prepare inositols: 1) stereoselective elaborations of the inexpensive, commercially available myo-inositol

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

• ; Introduction Inositol is a trivial name used to describe cyclohexanehexol compounds. Nine stereoisomers exist differing in the relative orientation of the hydroxy groups, the most naturally abounding and biologically important is myo-inositol [1][2]. The chemistry of inositols has been the theme of several

• this compound crosses the blood brain barrier (BBB) with difficulty [32]. The same PET imaging studies using the diastereoisomeric compound of myo configuration (2-[18F]fluoro-2-deoxy-myo-inositol), did not get better results [33]. On the other hand, these radiotracers have shown interesting features

• -inosose 7 [41] that can be easily obtained at large scale from commercially available myo-inositol. The introduction of the arm into the inositol backbone through an O–C linker (O-alkylated) or a C–C linker (C-branched) to afford diastereoselectively myo- and scyllo-derivatives was the key step. In the

Mycothiol synthesis by an anomerization reaction through endocyclic cleavage

• Shino Manabe and
• Yukishige Ito

Beilstein J. Org. Chem. 2016, 12, 328–333, doi:10.3762/bjoc.12.35

• Streptomycetes [5][6][7][8][9][10]. It consists of an N-acetylcysteine, a D-glucosamine, and a D-myo-inositol moiety (Figure 1). D-Glucosamine is α-linked to D-myo-inositol at the 1-position, and N-acetylcysteine is linked to the amino group of D-glucosamine. The conformation of MSH has been investigated by NMR

Synthesis of the calcilytic ligand NPS 2143

• Henrik Johansson,
• Thomas Cailly,
• Alex Rojas Bie Thomsen,
• Hans Bräuner-Osborne and
• Daniel Sejer Pedersen

Beilstein J. Org. Chem. 2013, 9, 1383–1387, doi:10.3762/bjoc.9.154

• was performed as previously described [20]. (R)-3 showed inhibition of calcium-stimulated D-myo-inositol monophosphate (IP1) accumulation in a concentration-dependent manner, with a potency consistent with that reported in the literature [21][22] (IC50 = 0.64 μM, pIC50 = 6.3 ± 0.2), thus confirming

Synthesis of glycoconjugate fragments of mycobacterial phosphatidylinositol mannosides and lipomannan

• Benjamin Cao,
• Jonathan M. White and
• Spencer J. Williams

Beilstein J. Org. Chem. 2011, 7, 369–377, doi:10.3762/bjoc.7.47

• crystal X-ray determination of (7S)-18. Thermal ellipsoids denote 20% electron probability. Indicative topology model for the biosynthesis of the glycophospholipids PIMs, LM and LAM in mycobacteria. The timing for translocation of PIM intermediates across the membrane is unclear. Hexagon = myo-inositol

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

• this work the synthesis of an cyclitol-derived scaffold designed to sequester Ag is presented. Interaction of myo-inositol-derived podands [6] and crown ethers [7] with Ag salts has been shown to depend on the relative spatial orientation of the binding sites moreover, in mono-orthoesters of scyllo

• ligation of this scaffold. Results and Discussion Chemistry The synthesis of 1 was accomplished in 6 steps from the readily available myo-inositol orthobenzoate (2) [17] (Figure 2). As scyllo-inositol derivatives are derived from myo-inositols by an oxidation/reduction sequence [8][18][19], selective