Towards the preparation of synthetic outer membrane vesicle models with micromolar affinity to wheat germ agglutinin using a dialkyl thioglycoside

• Dimitri Fayolle,
• Nathalie Berthet,
• Bastien Doumeche,
• Olivier Renaudet,
• Peter Strazewski and
• Michele Fiore

Beilstein J. Org. Chem. 2019, 15, 937–946, doi:10.3762/bjoc.15.90

• Fisher reaction between pyranoses and fatty alcohols of different lengths [8][9]. Alkyl thioglycosides are known for their properties as co-surfactants [10] and present interesting antimicrobial activities [11], acting as glycosidase inhibitors and being resistant towards glycoside hydrolases [12][13

Synthesis of polyhydroxylated decalins via two consecutive one-pot reactions: 1,4-addition/aldol reaction followed by RCM/syn-dihydroxylation

• Michał Malik and
• Sławomir Jarosz

Beilstein J. Org. Chem. 2016, 12, 2602–2608, doi:10.3762/bjoc.12.255

• to their similarity to carbohydrates, these compounds often possess interesting biological properties, e.g., they may act as glycosidase inhibitors [2][3][4]. One of such compounds, acarbose [5][6][7], found an application as a drug and is marketed worldwide. Five- and six-membered cyclitols are a

Exploring architectures displaying multimeric presentations of a trihydroxypiperidine iminosugar

• Camilla Matassini,
• Stefania Mirabella,
• Andrea Goti,
• Inmaculada Robina,
• Antonio J. Moreno-Vargas and
• Francesca Cardona

Beilstein J. Org. Chem. 2015, 11, 2631–2640, doi:10.3762/bjoc.11.282

• glycosidases. Keywords: dendrimers; glycosidase inhibitors; iminosugars; multivalency; piperidine alkaloids; Introduction Iminosugars are well-known naturally occurring glycomimetics with a nitrogen atom replacing the endocyclic oxygen, mainly recognized as inhibitors of carbohydrate-processing enzymes

• multivalent effect towards α-fucosidase inhibition, the tetravalent compound 8, the nonavalent compound 11.HCl, as well as the monovalent 15, were assayed as glycosidase inhibitors towards α-fucosidase (EC 3.2.1.51) from bovine kidney. Eight further commercially available glycosidases were also considered in

Synthesis of the first examples of iminosugar clusters based on cyclopeptoid cores

• Mathieu L. Lepage,
• Alessandra Meli,
• Anne Bodlenner,
• Céline Tarnus,
• Francesco De Riccardis,
• Irene Izzo and
• Philippe Compain

Beilstein J. Org. Chem. 2014, 10, 1406–1412, doi:10.3762/bjoc.10.144

• . Keywords: cyclopeptoids; glycosidases; iminosugars; inhibitors; multivalency; mutivalent glycosystems; Introduction Within a few years, the field of multivalent glycosidase inhibitors has witnessed tremendous advancement. Since the report in 2009 of the first quantifiable multivalent effect in glycosidase

A new approach toward the total synthesis of (+)-batzellaside B

• Jolanta Wierzejska,
• Shin-ichi Motogoe,
• Yuto Makino,
• Tetsuya Sengoku,
• Masaki Takahashi and
• Hidemi Yoda

Beilstein J. Org. Chem. 2012, 8, 1831–1838, doi:10.3762/bjoc.8.210

• ; L-pyroglutamic acid; total synthesis; Introduction Iminosugars, monosaccharide analogues in which the endocyclic oxygen has been replaced by nitrogen, display beneficial therapeutic activity as sugar-mimicking glycosidase inhibitors [1][2][3][4]. Since the discovery of nojirimycin (Figure 1), which

Carbohydrate-auxiliary assisted preparation of enantiopure 1,2-oxazine derivatives and aminopolyols

• Marcin Jasiński,
• Dieter Lentz and
• Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2012, 8, 662–674, doi:10.3762/bjoc.8.74

• as well as additional spots seen on TLC of the crude reaction mixtures support this assumption, but none of these possible by-products could be isolated. With respect to the enormous importance of polyhydroxylated N-heterocycles as carbohydrate-mimicking glycosidase inhibitors [41][42][43][44][45

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

• to the catalytic site [19]. In general, it is well known that a key issue in the design of glycosidase inhibitors is specificity, for example, 1-deoxynojirimycin (7) is a glycosidase inhibitor in the low micromolar range, but despite its activity it lacks specificity. In this study we wish to gain

Amine-linked diglycosides: Synthesis facilitated by the enhanced reactivity of allylic electrophiles, and glycosidase inhibition assays

• Ian Cumpstey,
• Jens Frigell,
• Elias Pershagen,
• Tashfeen Akhtar,
• Elena Moreno-Clavijo,
• Inmaculada Robina,
• Dominic S. Alonzi and
• Terry D. Butters

Beilstein J. Org. Chem. 2011, 7, 1115–1123, doi:10.3762/bjoc.7.128

• nitrogen atom bind more strongly to glycosidases than do the corresponding ether or thioether derivatives [5]. It follows that amine-linked diglycose derivatives may act as glycosidase inhibitors. We set about the synthesis of some compounds of this type to test this hypothesis. In our initial

• , possibly due to their presence in natural products and well known biological activities as glycosidase inhibitors [13]; second, electrophiles that are either lacking a bulky and electron-withdrawing substituent at one beta position [14] (making them less carbohydrate-like), or that are allylic [15], would

Synthesis of lipophilic 1-deoxygalactonojirimycin derivatives as D-galactosidase inhibitors

• Georg Schitter,
• Elisabeth Scheucher,
• Andreas J. Steiner,
• Arnold E. Stütz,
• Martin Thonhofer,
• Chris A. Tarling,
• Stephen G. Withers,
• Jacqueline Wicki,
• Katrin Fantur,
• Eduard Paschke,
• Don J. Mahuran,
• Brigitte A. Rigat,
• Michael Tropak and
• Tanja M. Wrodnigg

Beilstein J. Org. Chem. 2010, 6, No. 21, doi:10.3762/bjoc.6.21

• related β-galactosidase mutants. Keywords: chemical chaperones; 1-deoxy-D-galactonojirimycin; iminosugars; lipophilic galactosidase inhibitor; N-modified iminosugars; Introduction Iminosugars such as compounds 1–4 (Figure 1) have been shown to be potent glycosidase inhibitors and useful tools for the

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

• diols in the presence of p-toluenesulfonyl isocyanate for the introduction of the amino alcohol functionality. We are currently interested in the synthesis of cyclitols and their derivatives [25]. As a part of our program directed towards the synthesis of potential glycosidase inhibitors we used a

Indolizidines and quinolizidines: natural products and beyond

• Joseph P. Michael

Beilstein J. Org. Chem. 2007, 3, No. 27, doi:10.1186/1860-5397-3-27

• vertebrates; and both terrestrial and marine sources are represented. For example, two of the best-known and most widely investigated groups of 'simple izidine' alkaloids are the plant-derived polyhydroxylated indolizidines that function as potent glycosidase inhibitors, [2][3][4] and the alkylindolizidines

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

• glycosidase inhibitors obtained since this diversity is introduced in an ultimate step of the synthesis. Introduction There is a considerable interest in the design of molecules able to mimic carbohydrates which play critical roles in various biological events such as for example, cell-cell recognition and

Methods for the synthesis of polyhydroxylated piperidines by diastereoselective dihydroxylation: Exploitation in the two-directional synthesis of aza-C-linked disaccharide derivatives

• Andrew Kennedy,
• Adam Nelson and
• Alexis Perry

Beilstein J. Org. Chem. 2005, 1, No. 2, doi:10.1186/1860-5397-1-2

• is protonated at physiological pH and the transition state for glycosidase-catalysed reaction is mimicked effectively.[6] Glycosidase inhibitors have potential in the treatment of viral infections,[7][8][9][10] cancer[11][12] and diabetes and other metabolic disorders.[13][14][15] Aza-C-linked