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

• 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

• binds the large 50S ribosomal subunit to inhibit ribosomal peptidyl transferase activity [4][5] and contains three distinctive functional groups: furanose, cinnamic acid, and aminocyclitol (Figure 1). The cinnamic acid and aminocyclitol moieties directly restrict access of the amino-tRNA to inhibit

Efficient synthesis of aziridinecyclooctanediol and 3-aminocyclooctanetriol

• Emine Salamci and
• Ayse Kilic Lafzi

Beilstein J. Org. Chem. 2022, 18, 1539–1543, doi:10.3762/bjoc.18.163

• aziridine-fused derivatives. Some biologically active aziridine-bearing compounds 1, 2 and aminocyclitol 3. Synthesis of dimesylate 8. Synthesis of aminocyclooctanetriol 13. Synthesis of aziridinecyclooctanediol 16. Supporting Information Supporting Information File 344: Experimental section, 1H and 13C

Efficient and regioselective synthesis of dihydroxy-substituted 2-aminocyclooctane-1-carboxylic acid and its bicyclic derivatives

• İlknur Polat,
• Selçuk Eşsiz,
• Uğur Bozkaya and
• Emine Salamci

Beilstein J. Org. Chem. 2022, 18, 77–85, doi:10.3762/bjoc.18.7

• -oxabicyclo[5.2.1]decan-10-yl)carbamate was confirmed by X-ray diffraction. Keywords: aminocyclitol; azidolysis; bicyclic β-lactam; bicyclic lactone; cyclic β-amino acids; DFT; Introduction Cyclic β-amino acids have for the past few decades aroused widespread synthetic interest owing to their diverse

Stereoselective syntheses of 3-aminocyclooctanetriols and halocyclooctanetriols

• Emine Salamci and
• Yunus Zozik

Beilstein J. Org. Chem. 2021, 17, 705–710, doi:10.3762/bjoc.17.59

• replacement of one of the hydroxy groups with an amino group. Many aminocyclitols and their derivatives have been found to possess antibiotic properties, such as validamycins (1) [16]. Validamycin A (1) contains two aminocyclitol units, the one is valienamine (2) and the other is validamine (3, Figure 1). One

Regio- and stereoselective synthesis of new diaminocyclopentanols

• Evgeni A. Larin,
• Valeri S. Kochubei and
• Yuri M. Atroshchenko

Beilstein J. Org. Chem. 2014, 10, 2513–2520, doi:10.3762/bjoc.10.262

• - and stereoisomeric aminocyclitol derivatives remains in demand. One of the optimal routes involves the stereoselective ring opening of epoxides by different nucleophiles in the presence of a variety of activators [15][16][17][18][19]. In this context, epoxidation of cyclic allylic amines and

Synthesis and biological evaluation of nojirimycin- and pyrrolidine-based trehalase inhibitors

• Davide Bini,
• Francesca Cardona,
• Matilde Forcella,
• Camilla Parmeggiani,
• Paolo Parenti,
• Francesco Nicotra and
• Laura Cipolla

Beilstein J. Org. Chem. 2012, 8, 514–521, doi:10.3762/bjoc.8.58

• , which ensures the synergistic interactions of an aminocyclitol or a nitrogen-containing heterocycle with the catalytic site, and of a sugar or cyclitol unit with the recognition site. However, this work may highlight relevant structural features of the catalytic site that can give access to specific

Synthesis of a new class of aminocyclitol analogues with the conduramine D-2 configuration

• Latif Kelebekli,
• Yunus Kara and
• Murat Celik

Beilstein J. Org. Chem. 2010, 6, No. 15, doi:10.3762/bjoc.6.15

• Latif Kelebekli Yunus Kara Murat Celik Atatürk University, Faculty of Science, Department of Chemistry, TR-25240, Erzurum, Turkey 10.3762/bjoc.6.15 Abstract A new class of aminocyclitol derivatives with the bicyclo[4.2.0]octane skeleton was synthesized starting from cyclooctatetraene

• KMnO4 or OsO4 followed by acetylation gave the acetate derivatives, the exact configuration of which was determined by spectroscopic methods. Hydrolysis of the oxazolidinone rings and removal of the acetate groups furnished the desired aminocyclitols. Keywords: aminocyclitol; cyclitols; endoperoxide

• ; oxidation; X-ray analysis; Introduction Among the myriad of naturally occurring compounds are the aminocyclitol-containing natural products, which represent a large family of sugar derived microbial secondary metabolites and include the clinically active aminoglycoside inhibitors [1][2][3][4][5][6][7][8][9

Synthesis and glycosidase inhibitory activity of new hexa- substituted C8-glycomimetics

• Olivia Andriuzzi,
• Christine Gravier-Pelletier,
• Gildas Bertho,
• Thierry Prangé and
• Yves Le Merrer

Beilstein J. Org. Chem. 2005, 1, No. 12, doi:10.1186/1860-5397-1-12

• purification by ion-exchange chromatography, the targeted aminocyclitol 15 [20] (95% overall yield from 11). Alternatively, to obtain an analog of voglibose, the amine function of 13 could be alkylated via a reductive amination [39] with a dihydroxyacetone derivative. Thus, treatment of the amine 13 by the

• commercially available 2,2-dimethyl-1,3-dioxan-5-one in the presence of titanium(IV) tetra-isopropoxide followed by the cyanoborohydride reduction of the imine intermediate gave the expected N-alkylated aminocyclitol 17 (46% overall yield from 11). Then, simultaneous acidic hydrolysis of all protective groups