CNR Institute of Chemistry of Molecular Recognition

Roma, Italy

CNR Institute of Chemistry of Molecular Recognition

Roma, Italy

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Brenna E.,Polytechnic of Milan | Fuganti C.,Polytechnic of Milan | Gatti F.G.,Polytechnic of Milan | Serra S.,CNR Institute of Chemistry of Molecular Recognition
Chemical Reviews | Year: 2011

The enzymatic procedures that highlight the high stereoselectivity, and regioselectivity that can be achieved by using these methods, with the advantage of mild reaction conditions that do not require special expensive reagents or extreme working temperatures, are studied. Studies show that the avoidance of complex reagents or catalysts reduces the appearance of off-flavors in the samples of the final products because of the presence of chemical impurities. The avoidance of complex reagents or catalysts reduces the appearance of off-flavors in the samples of the final products because of the presence of chemical impurities. The concept of chiral switch, which is in pharmaceutical research, it is becoming a leading idea also in the field of chiral odorants, in the view of limiting the amount of chemicals which go in touch with living beings or which are inevitably dispersed in the environment. The enzyme-mediated approach obtains samples for a first screening of the odor properties of all the possible stereosiomers, and also for the enantioselective synthesis of the real odor vectors.


Serra S.,CNR Institute of Chemistry of Molecular Recognition
Natural Product Communications | Year: 2012

The enantioselective synthesis of (S)-1-hydroxy-1,3,5-bisabolatrien-10-one 1 is here described. This sesquiterpene was prepared using (S)-3-(2-methoxy-4- methyl-phenyl)butan-1-ol as a chiral building block. Two different pathways were employed and both turned out to be high yielding, affording 1 in good chemical purity and without any racemization of the existing stereocenter. The spectroscopic data of the synthetic (S)-1 were in very good agreement with those reported for the natural compound, which was extracted from Juniperus formosana heartwood and from the leaves of J. chinensis. The positive sign of the measured optical rotation value of synthetic (S)-1 allows the unambiguous assignment of the absolute configuration of (+)-1 as the (S)-enantiomer. This finding corrects the previous configuration determination which indicated the opposite result. At last, since even (R)-3-(2-methoxy-4-methyl-phenyl)butan-1-ol is preparable in high enantiomer purity by mean of a different biocatalytic process, the formal synthesis of natural (R)-1 was also accomplished.


Serra S.,CNR Institute of Chemistry of Molecular Recognition
Natural Product Communications | Year: 2013

The enantioselective syntheses of both the enantiomeric forms of the four natural tetralones 1a-d are here described. The aforementioned trinorsesquiterpenes were prepared starting either from substituted (S)-3-arylbutanols 5a-c or from substituted (S)-2-arylpropanols 7a-c. The latter chiral building blocks were in turn obtained through two different kinds of enzymatic transformations consisting of the baker's yeast mediated reduction of substituted (E)-3-aryl-but-2-enals 4a-c and the lipase-mediated resolution of racemic 2-arylpropanols 7a-c, respectively. Further key steps of the presented syntheses were C1 and C2 homologation procedures as well as the ring closure of the substituted 4-aryl-pentanoic acids 3a-c. By these means the target compounds were obtained in good yields and with very high stereoisomeric purity. In addition, the trinorsesquiterpene schiffnerone-B was synthesized for the first time and its absolute configuration was unambiguously assigned.


Sola L.,CNR Institute of Chemistry of Molecular Recognition | Chiari M.,CNR Institute of Chemistry of Molecular Recognition
Journal of Chromatography A | Year: 2012

Capillary electrophoresis (CE) is one of the most powerful techniques for the separation of biomolecules. However, the separation efficiency of proteins in CE is often compromised by their tendency to interact with the silanol groups on the surface of the inner capillary and by an uncontrolled electroosmotic flow. Herein, we report on the synthesis of novel hydrophilic polymeric coatings that can modulate the properties of the capillary walls. The novelty of these poly(N,. N-dimethylacrylamide)-based copolymers relies on the simultaneous presence of chemically reactive groups (N-acryloyloxysuccinimide and glycidyl methacrylate) and silane groups in the backbone, which results in highly stable films due to the covalent reaction between the polymer and the glass silanols. Although the functional monomers are reactive towards nucleophilic groups in proteins, they can be effectively blocked in the presence of amino modified agents. In addition, after a careful optimization of monomer concentration, it is possible to confer anti-fouling properties to the polymer coatings, and thus allow for highly efficient acidic and alkaline protein separations. Furthermore, the presence of these monomers makes it possible to modulate the electroosmotic flow from negligible to reduced values, depending on the desired application. © 2012 Elsevier B.V.


Serra S.,CNR Institute of Chemistry of Molecular Recognition
Natural Product Communications | Year: 2012

An expedient and concise synthesis of (S)-trans-γ-monocyclofarnesol is here described. The aforementioned sesquiterpene was prepared starting from enantioenriched (S)-γ-dihydroionone, which was in turn obtained from racemic α-ionone through the combined use of two previously developed processes. Key steps of the presented synthesis are the stereoselective Horner-Wadsworth-Emmons reaction between triethyl phosphonoacetate and γ-dihydroionone and the effective fractional crystallization of the γ-monocyclofarnesol-3,5-dinitrobenzoate esters. By these means the target compound was obtained in good yield and with very high stereoisomeric purity.


Monti D.,CNR Institute of Chemistry of Molecular Recognition | Ottolina G.,CNR Institute of Chemistry of Molecular Recognition | Carrea G.,CNR Institute of Chemistry of Molecular Recognition | Riva S.,CNR Institute of Chemistry of Molecular Recognition
Chemical Reviews | Year: 2011

An overview of the groups of oxidoreductases that are suitable for synthetic applications as isolated enzymes is presented. Studies have found that as compared to pyranose oxidases, PyDHs display broader substrate specificity and a variable regioselectivity and are unable to utilize oxygen as electron acceptor using substituted benzoquinones and organo metallic ions. A more precise control of the oxidation process and, higher yield of the isolated dimers is also achieved. Concerning the redox partners involved in cytochrome P450 catalytic activity, alternative types of redox systems have evolved in different organisms. Cytochrome P450-catalyzed heteroatom demethylation is studied for the regioselective deprotection of methylated monosaccharide derivatives. A P450 from B. megaterium ATCC 13368 (CYP106A2) capable of hydroxylating 3-keto-4-ene steroids mainly at position C-15 is cloned and characterized.


Serra S.,CNR Institute of Chemistry of Molecular Recognition
Flavour and Fragrance Journal | Year: 2013

We report the enantioselective synthesis of the ambergris odorants (+)-(S)-γ-ionone, (+)-(S)-γ-dihydroionone, (-)-α-ambrinol, (+)-(S)-γ-coronal, (-)-(S)-γ-homocyclogeranyl chloride and (+)-(S)-γ-homocyclogeraniol. At first, the enantio-enriched (4R,6S)-4-acetoxy-γ-ionone was prepared starting from commercial racemic ionone alpha by means of a chemo-enzymatic process. This chiral building block was then converted into (S)-γ-dihydroionone which was used as the starting material for the synthesis of the aforementioned odorants. © 2012 John Wiley & Sons, Ltd.


Secundo F.,CNR Institute of Chemistry of Molecular Recognition
Chemical Society Reviews | Year: 2013

Protein conformation plays a crucial role in determining both the catalytic efficiency and the chemo-, regio- and enantioselectivity of enzymes, thus eventually influencing their exploitability in biotechnological applications. Inevitably, immobilisation processes alter the natural molecular environment of enzymes, and quite often affect their catalytic activity through different mechanisms such as reduced accessibility of the substrate to the catalytic active centre, loss of the enzyme dynamic properties and alteration of the conformational integrity of the enzyme. This tutorial review outlines first the most common spectroscopic techniques used for investigating the conformation of immobilized proteins, and then examines how protein loading and polar and hydrophobic/hydrophilic interactions with the carrier affect the structural and dynamic features of enzymes. The nanoscale-level studies in which protein conformational changes, determined either by experimental approaches or by homology modelling, are correlated with the size and shape of the support are also discussed. Altogether, these results should provide useful information on how supports and/or enzymes have to be tailored to improve biocatalyst performance. © 2013 The Royal Society of Chemistry.


Vitali A.,CNR Institute of Chemistry of Molecular Recognition
Current Protein and Peptide Science | Year: 2015

Proline-rich peptides (PRPs) include a large and heterogeneous group of small-medium sized peptides characterized by the presence of proline residues often constituting peculiar sequences. This feature confers them a typical structure that determines the various biological functions endowed by these molecules. In particular the left-handed-polyproline-II helix is essential for the expression of the antimicrobial, immunomodulatory, antioxidant properties and to finely modulate protein-protein interactions, thus playing crucial roles in many cell signal transduction pathways. These peptides are widely diffuse in the animal kingdom and in humans, where they are present in many tissues and biological fluids. This review highlights the most relevant biological properties of these peptides, focusing on the potential therapeutic role that the PRPs may play as a promising source of new peptidebased novel drugs. © 2015 Bentham Science Publishers.


Serra S.,CNR Institute of Chemistry of Molecular Recognition
Tetrahedron Asymmetry | Year: 2011

A comprehensive study of the lipase-mediated resolution of substituted 2-aryl-propanols is reported. The latter alcohols were submitted to the irreversible acetylation catalyzed either by PPL, CRL, or lipase PS. The enantioselectivity of these transformations was dependent on the type of lipase used. The type of substituents and particularly their position on the aromatic ring strongly affected the selectivity of the reaction. The experiments described prove that PPL is the more versatile lipase catalyzing the acetylation with an enantiomeric ratio (E) value that ranges from 1 up to 144, depending on the substrate used. Conversely, the same transformations were catalyzed by CRL and lipase PS with an enantiomeric ratio value, which is always less than 5. The remarkable behavior of PPL was exploited in the large scale resolution of some substituted 2-aryl-propanols whose enantiomeric forms are relevant building blocks in the enantioselective synthesis of phenolic sesquiterpenes. By these means, the synthesis of (S)-turmeronol B and the formal syntheses of (R)-curcumene, (R)-curcuphenol, (R)-xanthorrhizol, and (R)-curcuhydroquinone were accomplished. © 2011 Elsevier Ltd. All rights reserved.

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