Synthesis of galactosides locked in a 1,4B boat conformation and functionalized at the anomeric position

Caravano, Audrey; Baillieul, Diane; Ansiaux, Christophe; Pan, Weidong; Kovensky, José; Sînaÿ, Pierre; Vincent, Stéphane

doi:10.1016/j.tet.2006.12.028

Cited by 15 publications

(9 citation statements)

References 29 publications

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“…For sugar tetrazoles, see: Brandstetter et al (1995); Davis et al (1995); Ermert et al (1991). For sugar triazoles, see: Caravano et al (2007); Krivopalov & Shkurko (2005); Krulle et al (1997); Marco-Contelles & Rodriguez-Fernandez (2001, 2002; Oikonomakos (2002); Tatsuta et al (1996). For related literature, see: Gö rbitz (1999); Larson (1970).…”

Section: Related Literaturementioning

confidence: 99%

“…Sugars with the ring oxygen replaced by nitrogen comprise a large family of both natural products and synthetic analogues which inhibit sugar metabolizing enzymes (Asano et al, 2000;Watson et al, 2001), including compounds which incorporate a tetrazole (Ermert et al, 1991;Davis et al, 1995;Brandstetter et al, 1995) or triazole (Tatsuta et al, 1996;Marco-Contelles & Rodriguez-Fernandez, 2002;Caravano et al, 2007;Krivpalov & Shkurko, 2007) fused to the pyranose ring. Some sugar triazoles have potential as glycogen phosphorylase inhibitors (Oikonomakos, 2002).…”

Section: S1 Commentmentioning

confidence: 99%

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(4S,5R,6R)-Methyl 4-hydroxy-4,5-isopropylidenedioxy-4,5,6,7-tetrahydro-1,2,3-triazolo[1,5-a]pyridine-3-carboxylate

et al. 2009

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X-ray crystallography confirmed the structure of the title triazole, C11H15N3O5, formed from a single-step reaction of a sugar azide with a brominated ylid. The absolute configuration was determined by the use of d-ribose as the starting material. The six-membered ring is in a half-chair conformation. The crystal structure exists as chains of O—H⋯O hydrogen-bonded moleclues running parallel to the b axis.

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Section: Related Literaturementioning

confidence: 99%

Section: S1 Commentmentioning

confidence: 99%

(4S,5R,6R)-Methyl 4-hydroxy-4,5-isopropylidenedioxy-4,5,6,7-tetrahydro-1,2,3-triazolo[1,5-a]pyridine-3-carboxylate

et al. 2009

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“…Indeed, when epoxide 25 was activated under acidic conditions, the C ‐furanoside 26 was formed as the major product (Scheme ). 1 H and 13 C NMR spectra of 26 and its acetate 27 were characteristic of a furanoside (for instance the weak J 2,3 coupling constant) as compared with very similar structures that were synthesized in our laboratory15b, 28 or by other groups 25. 26, 29 Having also in hand the corresponding α‐ and β‐phosphonylated C ‐galactopyranosides, 15g we could definitely conclude from the NMR spectroscopy data that compounds 26 – 31 are furanosides.…”

Section: Resultsmentioning

confidence: 69%

Reversible and Efficient Inhibition of UDP‐Galactopyranose Mutase by Electrophilic, Constrained and Unsaturated UDP‐Galactitol Analogues

Ansiaux

N’Go

Vincent

2012

Chemistry A European J

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A series of UDP-galactitols were designed as analogues of high-energy intermediates of the UDP-galactopyranose mutase (UGM) catalyzed furanose/pyranose interconversion, an essential step of Mycobacterium tuberculosis cell wall biosynthesis. The final compounds structurally share the UDP and the galactitol substructures that were connected by four distinct electrophilic connections (epoxide, lactone and Michael acceptors). All molecules were synthesized from a common perbenzylated acyclic galactose precursor that was derivatized by alkenylation, alkynylation and cyclopropanation. The inhibition study against UGM could clearly show that slight changes in the relative orientation of the UDP and the galactitol moieties resulted in dramatic variations of binding properties. Compared to known inhibitors, the epoxide derivative displayed a very tight, reversible, inhibition profile. Moreover, a time-dependent inactivation study showed that none of these electrophilic structures could react with UGM, or its FAD cofactor, the catalytic nucleophile of this still intriguing reaction.

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“…Compound 5 was treated with tetrabutylammonium fluoride to give iodo compound 6. As already described in the literature with similar structures, 16 this desilylation reaction required low temperatures. Even with rigorous control, the yield stayed moderate because of degradation byproducts.…”

Section: Figurementioning

confidence: 55%

Synthesis of Functionalized Bicyclic Precursors of Heptulosonic Acid Analogues

Filali¹,

Ballereau²,

Chahdi³

et al. 2009

Synthesis

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Synthesis of galactosides locked in a 1,4B boat conformation and functionalized at the anomeric position

Cited by 15 publications

References 29 publications

(4S,5R,6R)-Methyl 4-hydroxy-4,5-isopropylidenedioxy-4,5,6,7-tetrahydro-1,2,3-triazolo[1,5-a]pyridine-3-carboxylate

(4S,5R,6R)-Methyl 4-hydroxy-4,5-isopropylidenedioxy-4,5,6,7-tetrahydro-1,2,3-triazolo[1,5-a]pyridine-3-carboxylate

Reversible and Efficient Inhibition of UDP‐Galactopyranose Mutase by Electrophilic, Constrained and Unsaturated UDP‐Galactitol Analogues

Synthesis of Functionalized Bicyclic Precursors of Heptulosonic Acid Analogues

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