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6. ‘Direct Conversion’: Artificial Photosynthesis With Cyanobacteria

Author

Chen, Q., Montesarchio, D., Hellingwerf, K.J., Bruno, R., and Molecular Microbial Physiology (SILS, FNWI)

Abstract

Cyanobacteria, the only bacteria that can carry out oxygenic, (ie, plant-type) photosynthesis, can be engineered with the methods of synthetic biology so that they acquire the ability to convert CO2 directly into biofuel and/or commodity chemicals. In such an approach one bypasses the formation of the entire complex set of (macro)molecules that jointly form biomass. This approach has become known as ‘direct conversion’ (of CO2 and sunlight into biofuel) and has been shown to be feasible for several products already, even upon significant scaleup. Here we explain this concept of ‘direct conversion’ through natural photosynthesis and discuss its limitations and potential further improvement.

Published
2016

7. Solid Phase Synthesis of Glyco-Oligonucleotide Conjugates

Author

ADINOLFI, MATTEO, DE NAPOLI L., DI FABIO G., GUARINIELLO L., IADONISI A., MESSERE A., MONTESARCHIO D., PICCIALLI G., Adinolfi, M, DE NAPOLI, L, DI FABIO, Giovanni, Guariniello, L, Iadonisi, A, Messere, A, Montesarchio, D, Piccialli, G., Adinolfi, Matteo, DE NAPOLI, L., DI FABIO, G., Guariniello, L., Iadonisi, A., Messere, A., and Montesarchio, D.

Published
2001

9. New nucleoside based solid supports. Synthesis of 5 ',3 '-derivatized thymidine analogues

Author

DE CHAMPDORE’ M., DE NAPOLI L., DI FABIO G., MONTESARCHIO D., PICCIALLI G., MESSERE, Anna, DE CHAMPDORE’, M., DE NAPOLI, L., DI FABIO, G., Messere, Anna, Montesarchio, D., and Piccialli, G.

Subjects
GLYCOSYLATION, SCAFFOLD, LIBRARIES
Abstract

Two new thymidine based polymeric supports, in which the nucleosides have been anchored through the thymine moiety to a β-hydroxy thioether functionalized resin via a Mitsunobu reaction, have been prepared. A simple and efficient solid-phase synthesis of 5′,3′-bis-derivatized thymidine analogues has so been developed, following methodologies well established in peptide and oligonucleotide chemistry and is here proposed for the preparation of a variety of different nucleoside conjugate products. © 2001 The Royal Society of Chemistry.

Published
2001

12. A facile solid-phase strategy for the synthesis of oligonucleotide-tetraphenylporphprin conjugates

Author

DE NAPOLI L., DE LUCA S., DI FABIO G., MONTESARCHIO D., MORELLI G., PICCIALLI G., TESAURO D., MESSERE, Anna, DE NAPOLI, L., DE LUCA, S., DI FABIO, G., Messere, Anna, Montesarchio, D., Morelli, G., Piccialli, G., and Tesauro, D.

Subjects
Conjugation, Oligonucleotide, Porphyrinoid, Solid-phase synthesi
Abstract

A convenient solid-phase synthesis of oligonucleotides conjugated at the 3'-end with a tetraphenylporphyrin residue, by means of a new polymeric support bearing as a linker a lysine derivative, has been developed. A porphyrin linked 17-mer, designed for antisense experiments, has been prepared in good yields, and its hybridization properties with a complementary DNA fragment evaluated by UV thermal analysis.

Published
2000

13. Synthesis and conformation of dipeptide taste ligands containing homo-B-amino acid residues

Author

Isernia, C., Bucci, E., Napoli, L., Di Lello, P., Iacovino, R., Montesarchio, D., Piccialli, G., Rossi, F., Michele Saviano, Benedetti, E., C., Isernia, Bucci, Enrico, DE NAPOLI, Lorenzo, P., DI LELLO, R., Iacovino, Montesarchio, Daniela, Piccialli, Gennaro, Rossi, Filomena, Saviano, Michele, Benedetti, Ettore, Isernia, Carla, Bucci, E., DE NAPOLI, L., DI LELLO, P., Iacovino, Rosa, Montesarchio, D., Piccialli, G., Rossi, F., Saviano, M., and Benedetti, E.

Subjects
beta-aminoacid, Home-β-amino acid, Sweetner, Synthesi, conformational studie, dipeptide
Abstract

The synthesis and conformational properties of a series of dipeptide taste ligands, differing from the commercial sweetener aspartame by the presence of a methylene group between the Cα and the C′ carbon atoms (as in homo-β-residues) in either the L-Asp or the L-Phe residues, are described. Homo-β-residues such as homo-β-aspartic acid, homo-β-phenylglycine and homo-β-phenylalanine, obtained by homologation of the corresponding proteinogenic α-amino acids, have been used in the solution peptide synthesis of the following aspartame analogues in protected and unprotected forms: NH2-homo-β-(L or D)-Asp-L-Phe-OMe, NH2-L-Asp-homo-β-L-Phg-OMe and NH2-L-Asp-homo-β-L-Phe-OMe. Lengthening of the peptide skeleton at the L-Asp site results in a drastic loss of sweetness with the production of tasteless compounds; on the other hand, lengthening of the skeleton at the C-terminal L-Phe site partially mantains the sweet taste in both NH2-L-Asp-hamo-β-L-Phe-OMe and NH2-L-Asp-homo-β-L-Phg-OMe. The solution conformation of the synthesized dipeptide taste ligands was investigated by NMR and circular dichroism techniques. The analysis of NMR data combined with restrained molecular dynamics calculations shows that all peptides are fairly flexible and they do not assume a preferred conformation in DMSO and methanol. The peptides containing homo-β-L-Phe and homo-β-L-Phg do adopt a discrete number of conformation among which mainly extended and 'L-shaped' conformation are represented The circular dichroism spectra are consistent with the NMR results, indicating a significant flexibility for these compounds. Copyright © 1999 John Wiley & Sons, Ltd.

Published
1999

17. SOLID-PHASE SYNTHESIS OF CYCLIC OLIGODEOXYRIBONUCLEOTIDES - INTERMOLECULAR VERSUS INTRAMOLECULAR COUPLING

Author

DE NAPOLI L, MONTESARCHIO D, PICCIALLI G, SANTACROCE C, MAYOL L, GALEONE A, MESSERE, Anna, DE NAPOLI, L, Montesarchio, D, Piccialli, G, Santacroce, C, Mayol, L, Galeone, A, and Messere, Anna

Subjects
cyclization, cyclic oligonucleotide, solid phase synthesis
Abstract

Studies on the solid-phase synthesis of cyclic oligonucleotides using CPG or polyacrylamide as a solid matrix are reported. The former support was shown to be not suitable at all since it does not prevent intermolecular couplings. On the other hand, polyacrylamide resin allows the synthesis of medium-size cyclic oligonucleotides provided that the appropriate functionalization of the polymer is used.

Published
1991

29. Effect of lengthening of peptide backbone by insertion of chiral ?-homo amino acid residues: Conformational behavior of linear peptides containing alternatingL-leucine and ?-homoL-leucine residues

Author

Rossi, F., primary, Bucci, E., additional, Isernia, C., additional, Saviano, M., additional, Iacovino, R., additional, Romanelli, A., additional, Di Lello, P., additional, Grimaldi, M., additional, Montesarchio, D., additional, De Napoli, L., additional, Piccialli, G., additional, and Benedetti, E., additional

Published
2000
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46. An Efficient and Versatile Solid-Phase Synthesis of 5‘- and 3‘-Conjugated Oligonucleotides

Author

D'Onofrio, J., Montesarchio, D., Napoli, L. De, and Fabio, G. Di

Abstract

An easy and efficient solid-phase strategy to obtain 5‘- and 3‘-oligonucleotide conjugates in highly pure form has been developed. Ad hoc derivatized solid supports, to which the first nucleoside unit can be attached through a phosphate linkage, have been exploited both in a pre- and post-DNA assembly conjugation approach. A number of 5‘- or 3‘- oligonucleotide conjugates, incorporating a variety of labels covalently linked through a phosphodiester or a phosphoramidate bond, have been synthesized and characterized.

Published
2005

47. Glycomimetics as Decorating Motifs for Oligonucleotides:  Solid-Phase Synthesis, Stability, and Hybridization Properties of Carbopeptoid−Oligonucleotide Conjugates

Author

D'Onofrio, J., Champdore, M. de, Napoli, L. De, Montesarchio, D., and Fabio, G. Di

Abstract

The online solid-phase synthesis of oligonucleotides conjugated at the 3‘ end with [1−6]-linked oligosaccharide mimics having the O-glycosidic linkages replaced by amide bonds is here described. The assembly of the carbohydrate domain has been carried out by exploiting classical solid phase peptide synthetic protocols, starting from solid supports functionalized with 1-azido sugars, in association with suitably protected 1-azido uronic acids of glucose and lactose, chosen as model addition monomers. After the insertion of a flexible linker, elongation of the oligodeoxyribonucleotide (ODN) chain was performed by standard automated phosphoramidite protocols. 3‘-Glycoconjugated 18-mers exhibited an increased enzymatic stability with respect to the same unmodified ODN sequence. UV thermal denaturation experiments showed that the presence of the oligosaccharide tail at the 3‘ end of the oligonucleotides did not negatively interfere with their duplex formation abilities.

Published
2005

50. Effect of lengthening of peptide backbone by insertion of chiral -<TOGGLE>homo</TOGGLE> amino acid residues: Conformational behavior of linear peptides containing alternating <SC>L</SC>-leucine and -<TOGGLE>homo</TOGGLE> <SC>L</SC>-leucine residues <FNR HREF="fn1"></FNR> <FN ID="fn1">* Dedicated to the memory of Prof. Giacomino Randazzo</FN>

Author

Rossi, F., Bucci, E., Isernia, C., Saviano, M., Iacovino, R., Romanelli, A., Lello, P. Di, Grimaldi, M., Montesarchio, D., Napoli, L. De, Piccialli, G., and Benedetti, E.

Abstract

The synthesis and the solution behavior of the linear peptides containing a β-homo (β-H) leucine residue—Boc–Leu–β-HLeu–Leu–OMe, Boc–β-HLeu–Leu–β-HLeu–Leu–OMe, and Boc–Leu–β-HLeu–Leu–β-HLeu–Leu–OMe—as well as the solid structure of the tripeptide, are reported. The conformational behavior of the peptides was investigated in solution by two-dimensional nmr. Our data support the existence in solution with different families of conformers in rapid interchange. The crystals of the tripeptide are orthorhombic, space group P21212, with a = 15.829(1) Å, b = 29.659(1) Å, c = 6.563(1) Å, and Z = 4. The structure has been solved by direct methods and refined to final R1 and wR2 indexes of 0.0530 and 0.1436 for 2420 reflections with I > 2σ(I). In the solid state, the tripeptide does not present intramolecular H bonds, and the peptide backbone of the two leucine residues adopts a quasi-extended conformation. For the β-HLeu residue, the backbone conformation is specified by the torsion angles φ2 = −120.9(4)°, μ2 = 56.7(4)°, ψ3 = −133.2(4)°. The side chains of the three residues assume the same conformation (g−, g−, trans), and all peptide bonds, except the urethane group at the N-terminus, are in the trans conformation. Preliminary conformational energy calculations carried out on the Ac–NH–β-HAla–NHMe underline that the conformations with μ angle equal to 180° and 60° assume lower energy with respect to the others. In addition, we found a larger conformational freedom for the ψ angle with respect to the φ angle. © 2000 John Wiley & Sons, Inc. Biopoly 53: 140–149, 2000

Published
2000
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