Michelangelo Parrilli - Academia.edu (original) (raw)

Papers by Michelangelo Parrilli

Tetrahedron Letters, 2002

An efficient synthesis of a protected trisaccharide building block α-l-Rha(1→3)-α-l-Rha(1→2)-α-l-... more An efficient synthesis of a protected trisaccharide building block α-l-Rha(1→3)-α-l-Rha(1→2)-α-l-Rha related to the structure of many lipopolysaccharide O-chains from phytopathogenic bacteria has been developed. The protecting group pattern consisting of benzoyl, benzyl and chloroacetyl groups facilitated the use of the trisaccharide building block in the synthesis of two higher oligomers, an oligorhamnosyl hexasaccharide and a nonasaccharide.

Tetrahedron, 2005

3-Acetamido-3,6-dideoxy-d-galactopyranose (d-Fucp3NAc) is an aminosugar almost exclusively found ... more 3-Acetamido-3,6-dideoxy-d-galactopyranose (d-Fucp3NAc) is an aminosugar almost exclusively found in phytopathogenic O-antigens. The glycosylation reaction involving d-Fucp3NAc donors was studied with several rhamnosyl acceptors, revealing that the best yields and highest α-stereoselectivity were obtainable by coupling a N-phenyl trifluoroacetimidate glycosyl donor in a ternary mixture (dioxane/DME/toluene 4:1:1) as solvent. For the first time a synthetic access to α-d-Fucp3NAc containing oligorhamnans, that

Angewandte Chemie International Edition, 2011

... Bedini, E., De Castro, C., De Rosa, M., Di Nola, A., Iadonisi, A., Restaino, OF, Schiraldi, C... more ... Bedini, E., De Castro, C., De Rosa, M., Di Nola, A., Iadonisi, A., Restaino, OF, Schiraldi, C. and Parrilli, M. (2011), A ... 1 Department of Organic Chemistry and Biochemistry, University of Naples Federico II, Complesso Universitario Monte S.Angelo via Cintia 4, 80126 Naples (Italy ...

Tetrahedron, 1991

... MATTEO ADINOLFI, ROSA LANZETTA,* CARMELA ELSA MARCIANO, MICHELANGELO PARRILLI Dipartimento dl... more ... MATTEO ADINOLFI, ROSA LANZETTA,* CARMELA ELSA MARCIANO, MICHELANGELO PARRILLI Dipartimento dl Chimica Organica a Biologica, Universita&amp;amp;amp;#x27; di Napoli Via Mezzocannone 16, 80134 Napoli, Italy ALFONSO DE GIULIO Istituto per la Chimica delle Molecole di ...

Extremophiles : life under extreme conditions, Jan 21, 2016

Halomonas pantelleriensis DSM9661(Τ) is a Gram-negative haloalkaliphilic bacterium isolated from ... more Halomonas pantelleriensis DSM9661(Τ) is a Gram-negative haloalkaliphilic bacterium isolated from the sand of the volcanic Venus mirror lake, closed to seashore in the Pantelleria Island in the south of Italy. It is able to optimally grow in media containing 3-15 % (w/v) total salt and at pH between 9 and 10. To survive in these harsh conditions, the bacterium has developed several strategies that probably concern the bacteria outer membrane, a barrier regulating the exchange with the environment. In such a context, the lipopolysaccharides (LPSs), which are among the major constituent of the Gram-negative outer membrane, are thought to contribute to the restrictive membrane permeability properties. The structure of the lipid A family derived from the LPS of Halomonas pantelleriensis DSM 9661(T) is reported herein. The lipid A was obtained from the purified LPS by mild acid hydrolysis. The lipid A, which contains different numbers of fatty acids residues, and its partially deacylated ...

Phytochemistry, 1988

From the bulbs of Muscari neglecturn a novel scillascillinoid homoisoflavanone was isolated. The ... more From the bulbs of Muscari neglecturn a novel scillascillinoid homoisoflavanone was isolated. The quite unprecedented oxygenation pattern of its ring B was elucidated mainly by long-range 2D carbon 13-proton and proton-proton shift correlation experiments. Also isolated were scillascillin and four known 3-benzyl-4-chromanones.

This review collects the structural data of lipopolysaccharide components arising from all phytop... more This review collects the structural data of lipopolysaccharide components arising from all phytopathogenic bacteria so far investigated. The structural approaches and the main biological role of these macromolecules are also reported.

Phytochemistry, 1989

From the bulbs of Belleua[ia romana, a novel 3-benzyl-4-chromanone and a novel 3-benzylidene-4chr... more From the bulbs of Belleua[ia romana, a novel 3-benzyl-4-chromanone and a novel 3-benzylidene-4chromanone were isolated, besides known homoisoflavanones. Their structures were elucidated by spectral analysis (13C and 'H NMR, MS, CD).

Carbohydrate polymers, Jan 19, 2014

Rhodopseudomonas palustris is a purple photosynthetic bacterium characterized by a versatile natu... more Rhodopseudomonas palustris is a purple photosynthetic bacterium characterized by a versatile nature and a remarkable ability to adapt to various environments. In this work, we focused our attention to its membrane characteristics and defined the structural and conformational features of the O-chain polysaccharide of LPS isolated from R. palustris strain BisA53. This strain produces a polymer with a trisaccharide repeating unit characterized by d-rhamnose, 3-deoxy-d-lyxo-2-heptulosaric acid (Dha), and a novel C-branched monosaccharide, a 4-amino-4,6-dideoxy-3-C-methyl-2-O-methyl-α-l-glucopyranose whose absolute configuration has been determined by a combination of 2D NMR spectroscopy and molecular mechanic and dynamic simulation.

Phytochemistry, 1990

The isolation and the structure elucidation of ophiogenin 3-0-r-L-rhamnopyranosyl-(1-&/hoglucopyr... more The isolation and the structure elucidation of ophiogenin 3-0-r-L-rhamnopyranosyl-(1-&/hoglucopyranoside and bornyl 7-0-ol-L-arabinofuranosy1(1-*6)-/_(-D-glucopyranoside through spectral (NMR and FABMS) and chemical study is reported.

European Journal of Biochemistry, 2004

Pseudomonas stutzeri OXI is a Gram‐negative microorganism able to grow in media containing aromat... more Pseudomonas stutzeri OXI is a Gram‐negative microorganism able to grow in media containing aromatic hydrocarbons. A novel lipo‐oligosaccharide from P. stutzeri OX1 was isolated and characterized. For the first time, the presence of two moieties of 4,6‐O‐(1‐carboxy)‐ethylidene residues (pyruvic acid) was identified in a core region; these two residues were found to possess different absolute configuration. The structure of the oligosaccharide backbone was determined using either alkaline or acid hydrolysis. Alkaline treatment, aimed at recovering the complete carbohydrate backbone, was carried out by mild hydrazinolysis (de‐O‐acylation) followed by de‐N‐acylation using hot KOH. The lipo‐oligosaccharide was also analyzed after acid treatment, attained by mild hydrolysis with acetic acid, to obtain information on the nature of the phosphate and acyl groups. The two resulting oligosaccharides were isolated by gel permeation chromatography, and investigated by compositional and methylati...

Tetrahedron Letters, 1987

Tetrahedron, 2008

Recent studies have revealed that lipid-A and core fragments of the lipopolysaccharide from Xanth... more Recent studies have revealed that lipid-A and core fragments of the lipopolysaccharide from Xanthomonas campestris pv. campestris 8004 (Xcc), a phytopathogenic Gram-negative bacterium, are able to elicit plant immunity with two independent mechanisms. To date, nothing is known about the effect of the O-antigen portion. Since its separation from the core region by selective chemical degradation is very difficult, the chemical synthesis of related oligosaccharides is strictly necessary. In this paper a new, improved synthesis of the O-antigen repeating unit is presented. The main improvements in the synthesis are: (1) a shorter, high-yielding preparation of an efficient glycosyl donor of the rare sugar 3-acetamido-3,6-dideoxy-D-galactopyranose (3-acetamido-D-fucose, D-Fucp3NAc); (2) a new protecting group pattern, which is demonstrated to open a path to the future synthesis of higher oligomers.

Tetrahedron, 2006

... Emiliano Bedini Corresponding Author Contact Information , a , E-mail The Corresponding Autho... more ... Emiliano Bedini Corresponding Author Contact Information , a , E-mail The Corresponding Author ,Antonella Carabellese a , Daniela Comegna a , Cristina De Castro a and ... of compound 8 was started by treating the known diol 10 12 with BzCl in 2:1 CH 2 Cl 2 /Py at −30 °C to ...

Tetrahedron, 2002

possibility of performing the hydrolysis of cyclic acetals and ketals under basic or mildly alkal... more possibility of performing the hydrolysis of cyclic acetals and ketals under basic or mildly alkaline conditions by ceric ammonium nitrate (CAN) in MeCN/H 2 O or in 10% aq. methanol is rejected. However a role for Ce(IV) as Lewis acid is evidenced at pH 4.4. Under these conditions, which allow hydrolysis of cyclic ketals leaving glycosidic bonds unaltered, a selectivity of ketal cleavage due to steric hindrance is also observed. Similar yields are obtained when acetone/water replaces MeCN/H 2 O as solvent.

Tetrahedron, 1988

The ab8olute configuration of homolaoflavanonts isolated from Ru8carf 8pecias was determinsd by a... more The ab8olute configuration of homolaoflavanonts isolated from Ru8carf 8pecias was determinsd by applying the chiral excfton coupling method to suitable derivatives. A negative Cotton effect In the 287-295 nm region of the CD curve8 of the natural compounds 1118 8hom to bs indicative of 3R-configuration. In the ~018-88 of our 8tudie8 $1) on the homolsoflwonoid Content Of hfU8Cui 8peCfeII \tifiaceae). msny compound8 of this cls88 of natural product8 have bean i8olatcd, both with the 3

Rapid Communications in Mass Spectrometry, 2003

Lipooligosaccharides (LOSs) are macromolecules present on the external cellular membrane of Gram‐... more Lipooligosaccharides (LOSs) are macromolecules present on the external cellular membrane of Gram‐negative bacteria, structurally made of two distinct regions, lipid A and Core. By varying their growth temperature, bacteria such as psychrophiles change the phosphorylation distribution of the LOSs produced. The level of phosphorylation and the phosphate group positions in LOSs produced by the extremophile psychrophilic bacterium Pseudoalteromonas haloplanktis TAC 125, grown at 15°C and 25°C, were investigated by nano‐electrospray ionization quadrupole time‐of‐flight mass spectrometry (nanoESI‐QTOF‐MS) and tandem mass spectrometry (MS/MS). The samples, obtained by phenol/chloroform/petroleum ether (PCP) extraction of dried cells, were treated with hydrazine at 37°C in order to reduce the heterogeneity by removal of the ester‐linked fatty acid moieties. The molecular ion distributions in these LOS fractions were investigated in negative ion mode. Based on these data it was postulated th...

Planta Medica, 1989

For benign prostatic hyperplasia (BPH), the sexual steroids are discussed as being the main etiol... more For benign prostatic hyperplasia (BPH), the sexual steroids are discussed as being the main etiological factors. Especially, testosterone obviously exerts a lifelong stimulus for proliferation on the prostatic tissue. Testosterone has to be converted into 5a-dihydrotestosterone (DHT) in order to act at the prostatic level, therefore, the enzyme 5ct-reductase is thought to play a key role in inducing and maintaining the BPH.

Magnetic Resonance in Chemistry, 1986

... 24, 663-666 (1986) &amp;amp;#x27;H and &amp;amp;quot;C Chemical Shift Assignm... more ... 24, 663-666 (1986) &amp;amp;#x27;H and &amp;amp;quot;C Chemical Shift Assignments of Homoisoflavanones Matteo Adinolfi,Rosa Lanzetta, Guglielmo Laonigro and Michelangelo Parrilli&amp;amp;quot; Dipartimento di Chimica Organica e Biologica, Universith di Napoli, Via Mezzocannone 16, 80134 Napoli, Italy ...

Biological Mass Spectrometry, 1984

The structure elucidation of a novel branched-chain hexasaccharide glycoside, muscaroside B, has ... more The structure elucidation of a novel branched-chain hexasaccharide glycoside, muscaroside B, has been aided by fast atom bombardment mass spectrometry. Muscaroside A-a straight-chain analogue having the same 27-norlanostane skeleton and spirofused tetrahydrofuran ring-and digitonin-a branched-chain steroidal glycoside-were used as standards.