Rui Galhano dos Santos

Fries-type Reactions for the C-Glycosylation of Phenols

C-Glycosylphenols and -polyphenols occur widely in nature and present a variety of biological properties, namely antitumor, antibacterial and antidiabetic activities. Synthetic access to such structures relies mainly on efficient methodologies for phenols C- glycosylation. In the past few years major advances have been described addressing the use of Fries rearrangement to obtain a diversity of C-glycosyl compounds. Herein we survey the glycosyl donors and the activators used for this reaction, covering both early work and recent developments in the area. Reaction mechanism and reaction outcome control, aiming at regio- and stereoselectivity are also dis- cussed.

The multidrug resistance transporters CgTpo1_1 and CgTpo1_2 play a role in virulence and biofilm formation in the human pathogen Candida glabrata

The mechanisms of persistence and virulence associated with Candida glabrata infections are poorly understood, limiting the ability to fight this fungal pathogen.

New Mechanisms of Flucytosine Resistance in C. glabrata Unveiled by a Chemogenomics Analysis in S. cerevisiae.

5-Flucytosine is currently used as an antifungal drug in combination therapy, but fungal pathogens are rapidly able to develop resistance against this drug, compromising its therapeutic action. The understanding of the underlying resistance mechanisms is crucial to deal with this problem. In this work, the S. cerevisiae deletion mutant collection was screened for increased resistance to flucytosine. Through this chemogenomics analysis, 183 genes were found to confer resistance to this antifungal agent. Consistent with its known effect in DNA, RNA and protein synthesis, the most significant Gene Ontology terms over-represented in the list of 5-flucytosine resistance determinants are related to DNA repair, RNA and protein metabolism. Additional functional classes include carbohydrate and nitrogen—particularly arginine—metabolism, lipid metabolism and cell wall remodeling. Based on the results obtained for S. cerevisiae as a model system, further studies were conducted in the pathogenic yeast Candida glabrata. Arginine supplementation was found to relieve the inhibitory effect exerted by 5-flucytosine in C. glabrata. Lyticase susceptibility was found to increase within the first 30min of 5-flucytosine exposure, suggesting this antifungal drug to act as a cell wall damaging agent. Upon exponential growth resumption in the presence of 5-flucytosine, the cell wall exhibited higher resistance to lyticase, suggesting that cell wall remodeling occurs in response to 5-flucytosine. Additionally, the aquaglyceroporin encoding genes CgFPS1 and CgFPS2, from C. glabrata, were identified as determinants of 5-flucytosine resistance. CgFPS1 and CgFPS2 were found to mediate 5-flucytosine resistance, by decreasing 5-flucytosine accumulation in C. glabrata cells.

Heuristic Analysis of the Effective Range of a Track Tamping Machine

This paper develops a methodology to define the optimum length of railway track that would undergo maintenance work by one tamping machine. The acquisition and logistic costs associated with the use of this type of machine are very relevant in the context of track maintenance. However, no systematic approach was found in the literature that could help managers recognize the machines’ real capacity, which seems to be more conditioned by the track’s availability for maintenance than by the machine’s performance. The methodology presented in this paper takes into account the execution capacity of the machine in a scenario in which the intervention schedule is optimized from a long-term perspective. It employs a metaheuristic process (simulated annealing) to deliver an optimized intervention schedule and the model is applied to several track length configurations. A trade-off approach is therefore adopted, confronting the minimum logistic costs with the fixed costs of the machine. The implementation of the algorithm showed significant cost reduction. However, the results of the model showed a deviation of the minimum cost solution from the quality standards. Further research could provide more insight into quality standards through its integration into a multiobjective analysis.

Learning to combine multiple string similarity metrics for effective toponym matching

ABSTRACT Several tasks related to geographical information retrieval and to the geographical information sciences involve toponym matching, that is, the problem of matching place names that share a common referent. In this article, we present the results of a wide-ranging evaluation on the performance of different string similarity metrics over the toponym matching task. We also report on experiments involving the usage of supervised machine learning for combining multiple similarity metrics, which has the natural advantage of avoiding the manual tuning of similarity thresholds. Experiments with a very large dataset show that the performance differences for the individual similarity metrics are relatively small, and that carefully tuning the similarity threshold is important for achieving good results. The methods based on supervised machine learning, particularly when considering ensembles of decision trees, can achieve good results on this task, significantly outperforming the individual similarity metrics.

Upcycling potato peel waste - Data of the pre-screening of the acid-catalyzed liquefaction.

Herein, the data acquired regarding the preliminary and exploratory experiments conducted with potato peel as a biomass source for the direct thermochemical liquefaction is disclosed. The procedure was carried out in a 2-ethylhexanol/DEG solvent mixture at 160 °C in the presence of p-Toluenesulfonic acid. The adopted procedure afforded a bio-oil in high yield (up to 93%) after only 30 min. For longer reaction times, higher amounts of solid residues were obtained leading, consequently, to lower yields.

One-Component Spray Polyurethane Foam from Liquefied Pinewood Polyols: Pursuing Eco-Friendly Materials

The use of petroleum-derived products should be avoided regarding the principles of green and sustainable chemistry. The work reported herein, is aimed at the liquefaction of pine shavings for the production of an environmentally-friendly polyol suitable to be used in the formulations of sprayable polyurethane foams. The biopolyols were obtained in high yield and were used to replace those derived from fossil sources, to produce more “greener” polyurethane foams and therefore, less dependent on petroleum sources, since the polyol component was substituted by products resulting from biomass liquefaction. The partial and fully exchange of the polyols was accomplished, and the results compared with a reference foam. The foams were afterward, chemical, physical, morphological, and mechanically characterized. The complete replacement of polyether polyol and polyol polyester has presented some similar characteristics as that used as a reference, validating that the path chosen for the development of more sustainable materials is on the right track for the contribution to a cleaner world.

Toponym matching through deep neural networks

ABSTRACT Toponym matching, i.e. pairing strings that represent the same real-world location, is a fundamental problemfor several practical applications. The current state-of-the-art relies on string similarity metrics, either specifically developed for matching place names or integrated within methods that combine multiple metrics. However, these methods all rely on common sub-strings in order to establish similarity, and they do not effectively capture the character replacements involved in toponym changes due to transliterations or to changes in language and culture over time. In this article, we present a novel matching approach, leveraging a deep neural network to classify pairs of toponyms as either matching or nonmatching. The proposed network architecture uses recurrent nodes to build representations from the sequences of bytes that correspond to the strings that are to be matched. These representations are then combined and passed to feed-forward nodes, finally leading to a classification decision. We present the results of a wide-ranging evaluation on the performance of the proposed method, using a large dataset collected from the GeoNames gazetteer. These results show that the proposed method can significantly outperform individual similarity metrics from previous studies, as well as previous methods based on supervised machine learning for combining multiple metrics.

A New Determinant of Candida glabrata Virulence: The Acetate Exporter CgDtr1

Persistence and virulence of Candida glabrata infections are multifactorial phenomena, whose understanding is crucial to design more suitable therapeutic strategies. In this study, the putative multidrug transporter CgDtr1, encoded by ORF CAGL0M06281g, is identified as a determinant of C. glabrata virulence in the infection model Galleria mellonella. CgDTR1 deletion is shown to decrease the ability to kill G. mellonella larvae by decreasing C. glabrata ability to proliferate in G. mellonella hemolymph, and to tolerate the action of hemocytes. The possible role of CgDtr1 in the resistance to several stress factors that underlie death induced by phagocytosis was assessed. CgDTR1 was found to confer resistance to oxidative and acetic acid stress. Consistently, CgDtr1 was found to be a plasma membrane acetic acid exporter, relieving the stress induced upon C. glabrata cells within hemocytes, and thus enabling increased proliferation and virulence against G. mellonella larvae.

Synthesis and Characterization of Isosorbide-Based Polyurethanes Exhibiting Low Cytotoxicity Towards HaCaT Human Skin Cells

The synthesis of four samples of new polyurethanes was evaluated by changing the ratio of the diol monomers used, poly(propylene glycol) (PPG) and D-isosorbide, in the presence of aliphatic isocyanates such as the isophorone diisocyanate (IPDI) and 4,4′-methylenebis(cyclohexyl isocyanate) (HMDI). The thermal properties of the four polymers obtained were determined by DSC, exhibiting Tg values in the range 55–70 °C, and their molecular structure characterized by FTIR, 1H, and 13C NMR spectroscopies. The diffusion coefficients of these polymers in solution were measured by the Pulse Gradient Spin Echo (PGSE) NMR method, enabling the calculation of the corresponding hydrodynamic radii in diluted solution (1.62–2.65 nm). The molecular weights were determined by GPC/SEC and compared with the values determined by a quantitative 13C NMR analysis. Finally, the biocompatibility of the polyurethanes was assessed using the HaCaT keratinocyte cell line by the MTT reduction assay method showing values superior to 70% cell viability.