CARMONA ASENJO , Ana Teresa

The synthesis of chiral furan amino acid analogues of D - and L -serine is reported. The developed methodology starting from D -xylose affords the corresponding amino acid derivative analogue of D -serine enantiomerically pure. Starting from D -arabinose, the corresponding analogue of L -serine was isolated in 92.3% enantio- meric...

We present herein a selection of ingenious methods that have been developed to convert inexpensive furan, pyrrole and unsaturated hydrocarbons into enantiomerically enriched monosaccharides and analogues of biological interest.

Since the discovery of the 'formose reaction' by Butlerow,[1] total synthesis of carbohydrates has undergone rapid development. The most important methods for the asymmetric synthesis of monosaccharides and analogues of biological importance are presented. Nowadays any natural and non-natural monosaccharide can be prepared pure in both...

In recent years, Saturation Transfer Difference NMR (STD NMR) has been proven to be a powerful and versatile ligand-based NMR technique to elucidate crucial aspects in the investigation of protein-ligand complexes. Novel STD NMR approaches relying on "multi-frequency" irradiation have enabled us to even elucidate specific ligand-amino acid...

Iminosugar derivatives containing a pyrrolidine-phosphine moiety were prepared from carbohydrates and used as catalysts in the [3 + 2] cycloaddition reaction between alkyl allenoates and electron-deficient imines. The corresponding 1,2,3,5-tetrasubstituted pyrrolines were obtained in good yields and diastereoselectivities but with moderate...

The synthesis of 3-substituted l-fuco-azafagomines from d-lyxose is reported. They represent the first example of aza-C-glycosides having a biimino (-NH-NH-) moiety. The key step of the synthesis is the introduction of the hydrazine moiety by reductive hydrazination of a 1-deoxy-ketohexose with tert-butyl carbazate. Their glycosidase inhibitory...

A review dealing with 1,4-iminoalditol (hydroxylated pyrrolidine) derivatives as inhibitors of α-l-fucosidases including the different synthetic approaches for their preparation as well as their inhibitory properties is presented.

Tiofucósidos conteniendo prolinas hidroxiladas, síntesis y usos de los mismos. Compuesto que comprende un tiofucósido conteniendo prolinas hidroxiladas. La invención también se refiere al método de obtención de dicho compuesto y a su aplicación en el tratamiento de alteraciones o desórdenes en los que intervienen selectinas, como, por ejemplo,...

Iminosugars are carbohydrate mimetics that constitute the main group of oligosaccharide processing enzyme inhibitors. They play an important role in cell-cell recognition processes, thereby presenting a wide range of potential therapeutic applications. In this work, we present the first examples of glycopolymers containing five-membered...

Tiofucósidos conteniendo polihidroxialquil-furanos, síntesis y usos de los mismos. Compuesto que comprende un tiofucósido conteniendo polihidroxialquil-furanos. La invención también se refiere al método de obtención de dicho compuesto y a su aplicación en el tratamiento de alteraciones o desórdenes en los que intervienen selectinas, como, por...

The use of 7-oxa/azanorbornadienes as synthetic intermediates for the preparation of 3/4-substituted (β-substituted) furans/pyrroles is presented. The method lies in the inverse electron demand Diels-Alder (iEDDA) cycloaddition between a substituted heteronorbornadiene and an electron-poor tetrazine followed by spontaneous fragmentation of the...

Through the reductive amination of N-[(tert-butoxy)carbonyl]-2,5-dideoxy-2,5-imino-3,4-Oisopropylidene-L-ribose with tetramethylenediamine, hexamethylenediamine, 2,7- diaminofluorene, 4,4'-diaminodiphenylmethane and 1,4-(diaminomethyl)benzene, five tetramines containing two (2R,3R,4S)-2-aminomethylpyrrolidine-3,4-diol moieties have...

Through the reductive amination of N-[(tert-butoxy)carbonyl]-2,5-dideoxy-2, 5-imino-3,4-O-isopropylidene-L-ribose with tetramethylenediamine, hexamethylenediamine, 2,7-diaminofluorene, 4,4′-diaminodiphenylmethane and 1,4-(diaminomethyl)benzene, five tetramines containing two (2R,3R,4S)-2- aminomethylpyrrolidine-3,4-diol moieties have been...

Aminoglycosides are powerful antibiotics, but the emergence of resistant bacterial strains has prompted the search for analogues with better pharmacological profiles. The synthesis of 2-deoxystreptamine (2-DOS) dimers linked by polyamines and analogues based on furylcarbopeptoid skeletons is described. Potent and selective ligands for bacterial...

2-Halo-3-tosyl-oxanorbornadienes are able to accept two thiol molecules through an initial nucleophilic substitution, giving isolable oxabicyclic thiovinyl sulfones that, subsequently, can react with a second thiol molecule via thio-Michael addition. The resulting oxanorbornenic thioketals undergo retro-Diels-Alder (rDA) fragmentation to...

Ligand-based NMRtechniquesto studyprotein–ligandinteractionsare potenttoolsin drugdesign.Satura-tiontransfer difference (STD)NMRspectroscopystandsoutas one of the mostversatiletechniques,allowing screeningof fragmentslibraries andproviding structural informationon bindingmodes.Recently,ithas beenshown that amulti-frequencySTD NMRapproach,...

Two libraries of mono- and dimeric pyrrolidine iminosugars were synthesized by CuAAC and (thio)urea-bond-forming reactions from the respective azido/aminohexylpyrrolidine iminosugar precursors. The resulting monomeric and dimeric compounds were screened for inhibition of β-N-acetylglucosaminidase from Jack beans, the plant ortholog of human...

The parallel synthesis of a 26-membered-library of aromatic/aliphatic-(thio)urea-linked pyrrolizidines followed by in situ biological evaluation toward α -galactosidases has been carried out. The combination of the (thio)urea-forming click reaction and the in situ screening is pioneer in the search for glycosidase inhibitors and has allowed the...

Cancer cells are highly dependent on Nicotinamide phosphoribosyltransferase (NAMPT) activity for proliferation, therefore NAMPT represents an interesting target for the development of anti-cancer drugs. Several compounds, such as FK866 and CHS828, were identified as potent NAMPT inhibitors with strong anti-cancer activity, although none of them...