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Sandrine Gerber

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Related publications (98)

Spongistatins : biological activity and synthetic studies

During the last two decades, marine organisms such as sponges, tunicates, softcoral and starfish proved to be productive sources of structurally complex metabolites presenting unprecedented architectures.[1] These marine natural products often display unex ...

2008

Functionalized pyrrolidine inhibitors of human alpha- mannosidases II in cancer: optimizing the fit to the active site

Sandrine Gerber, Hélène Fiaux

Refining the chemical structure of functionalized pyrrolidine-based inhibitors of Golgi α- mannosidase II (GMII) to optimize binding affinity provided a lead molecule that demonstrated nanomolar competitive inhibition of α-mannosidases II and an optimal fi ...

2008

Preparation and synthetic applications of 8-oxabicyclo[3.2.1]oct-6-en-3-one derivatives

Pierre Vogel, Sandrine Gerber, Sylvain Favre

The development of efficient routes to multi gram quantities of chiral synthons is a key issue in total synthesis of natural products and analogues. The conformationally defined and rigid 8-oxabicyclo[3.2.1]oct-6-en-3-one template appears as an appealing s ...

2008

Recent Synthetic Approaches Toward Non-anomeric Spiroketals in Natural Products

Pierre Vogel, Sandrine Gerber, Sylvain Favre

Many natural products of biological interest contain [6,5]- and [6,6]-spiroketal moieties that can adopt various configurations, benefiting or not from anomeric conformation stabilizing effects. The spiroketal fragments are often important for the biologic ...

2008

Evaluation of docking programs for predicting binding of Golgi alpha-mannosidase II inhibitors: a comparison with crystallography

Sandrine Gerber, Hélène Fiaux

2007

New efficient route to an advanced precursor of the AB spiroketal of spongistatins

Pierre Vogel, Sandrine Gerber, Sylvain Favre

2007

Efficient synthesis of cyclic glycolipids analogues

Sandrine Gerber, Gérald Coste

A straightforward approach to macrocyclic structures containing deoxysugar subunits was developed through the functionalization of a bishemiketal. The choice of the length and the nature of the linkers can provide macrocycles with diverse rigidities and po ...

2007

Asymmetric synthesis of the polyol subunit of the polyene macrolide antibiotic RK-397

Kai Torsten Meilert, Pierre Vogel, Sandrine Gerber

A total asymmetric synthesis of the polyol subunit of the polyene macrolide antibiotic RK-397 was developed through the stereoselective functionalization of (1R,1’S,6S,6’R)-3,3’-methylenebis(cyclohept-3-ene-1,6-diol). The pathway generates a large variety ...

2006

Synthesis of new pyrrolidine derivatives as inhibitors of alpha-mannosidase and of glioblastoma cells growth

Pierre Vogel, Sandrine Gerber, Sylvain Favre, Hélène Fiaux

New 2-benzylamino-3,4-dihydroxypyrrolidines bearing aromatic and aliphatic amido side chains have been prepared. The influence of the amido substituents on the inhibitory activity of these diamines toward 24 commercially available glycosidases was determin ...

2006

New efficient synthesis of long chain di- and tri-aminopolyols

Sandrine Gerber, Gérald Coste

The asymmetric synthesis of long chain di- and tri-amino polyols is reported. The developed methodology is based on the functionalization of 3,3'-methylenebis{[6-(benzyloxy)methoxy]cyclohept-3-en-1-ol} derivatives that allows the selective introduction of ...

2006

Pyrrolidine derivatives as new inhibitors of alpha-mannosidases and growth inhibitors of human cancer cells

Pierre Vogel, Sandrine Gerber, Hélène Fiaux

New pyrrolidine-3,4-diol derivatives were prepared from D-(-)- and L(+)-phenylglycinol and tested for their ability to inhibit 25 commercial glycosidases. The influence of the substitution of the lateral side chain and of the pyrrolidine ring on the enzyme ...

2006

Selective hydrolysis of anti-1,3-diol-acetonides for the differentiation of 1,3-anti and 1,3-syn diols

Sandrine Gerber, Gérald Coste

A mild and general method for the selective cleavage of anti-1,3-acetonides has been developed for the differentiation of 1,3-anti and 1,3-syn diols in long chain polyolic fragments. The diluted acidic conditions applied to these systems are compatible wit ...

Elsevier2006

Trifluoromethanesulfonyl chloride, first update

Pierre Vogel, Sandrine Gerber

2006

Glycosylation pathways as drug targets for cancer: glycosidase inhibitors

Sandrine Gerber

The combined and ordered sequential action of glycosidases and glycosyltransferases in mammalian cell compartments leads to the addition of defined glycans to proteins and lipids. Altered glycosylation patterns, neoexpression, underexpression or overexpres ...

2006

New synthetic route toward polyketide-like macrolides

Sandrine Gerber, Gérald Coste

New pathways toward the synthesis of polyketide-like macrolides have been developed through the functionalization of long chain polyolic fragments readily obtained from 3,3'-methylenebis{[6-(benzyloxy)methoxy]cyclohept-3-en-1-ol} derivatives 6. This synthe ...

2006

Noniterative approach to the total asymmetric synthesis of 15-carbon polyketides and analogs with high stereodiversity

Marc-Etienne Schwenter, Kai Torsten Meilert, Pierre Vogel, Sandrine Gerber

Starting from inexpensive furan and furfuryl alcohol, a noniterative approach to the synthesis of pentadeca-1,3,5,7,9,11,13,15-octols and their derivatives has been developed. The method relies upon the double [4+3]-cycloaddition of 1,1,3-trichloro-2-oxyla ...

2005

Enzymatic desymmetrization of 1,1 '-methylenedi-[(1R,1 ' S,3R,3 ' S,5S,5 ' R)-3-hydroxy-8-oxabicyclo[3.2.1]-oct-6-ene-1-yl]: Novel precursors of long chain polyketides

Sandrine Gerber, Gérald Coste

meso-1,1'-Methylenedi[(1R,1'S,3R,3'S,5S,5'R)-3-hydroxy-S-oxabicyclo[3.2. 1]oct-6-ene-1-yl] 14 obtained through the [4+3]-cycloaddition of 2,T-methylenedifuran to oxyallyl cation, followed by reduction, has been desymmetrized by means of a lipase catalyzed ...

2005

Functionalized pyrrolidines as alpha-mannosidase inhibitors and growth inhibitors of human glioblastoma and melanoma cells

Pierre Vogel, Sandrine Gerber, Sylvain Favre, Hélène Fiaux

New substituted pyrrolidine-3,4-diol derivatives were prepared from D-(-)- and L-(+)-phenyl glycinol. The influence of the configuration and the substitution of the lateral side chain of these derivatives on the inhibition of 25 commercial glycosidases wer ...

2005

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