The further development of a general and flexible methodology for the elaboration of polypropionate subunits, which are a common feature of macrolides and ionophores will be addressed. This will be done by means of oxirane chemistry coupled to other stereoselective synthetic transformations. Carbonate extension and iodolactonization reactions are key to this procedure. Initially a general hydroxyl group inversion methodology will be studied in detail in order to complement the all syn- polyol sequence generated from the carbonate extension reaction. This will allow for the construction of a polypropionate unit in which the hydroxyl functions can have any given stereochemistry. Alternatively an epoxide inversion sequence will also be developed. This will be based on the regioselectivity of the hydroxyl assisted oxirane opening and will allow for the simultaneous inversion of two centers. A variation of the carbonate extension reaction in which the intermediate iodocarbonate is transformed into an iodoacetonide will be studied. This new intermediate is a masked hindered oxirane and its electrophilic chemistry will be studied. This can be a solution to the lack of reactivity of hindered epoxides. Finally, we will like to apply this methodology to the synthesis of the polyketide chain of the ansamycin antibiotics rifamycin S and streptovaricin V. These compounds have received much attention due to their notable biological activity. This will be accomplished via the general reiterative procedure which we have been developing together with the above studies. Although this methodology is intended for these targets, it can be extended to the synthesis of other families of products. In summary, it is intended to develop and improve methodologies for the synthesis of these important biologically active targets as a contribution to this expanding field.
| García-Arriaga, Marilyn; Acosta-Santiago, Maxier; Cruz, Antony et al. (2017) Probing the Limits of Supramolecular G-Quadruplexes Using Atomistic Molecular Dynamics Simulations. Inorganica Chim Acta 468:209-222 |
| Ramírez-Camejo, Luis A; Maldonado-Morales, Génesis; Bayman, Paul (2017) Differential Microbial Diversity in Drosophila melanogaster: Are Fruit Flies Potential Vectors of Opportunistic Pathogens? Int J Microbiol 2017:8526385 |
| Morales-Rivera, Keyla F; Piñero Cruz, Dalice M; Prieto, Jose A (2017) Crystal structure of (-)-(S)-4-[(2S,3S,4S,Z)-3-hydroxy-4-methyl-hept-5-en-2-yl]-1,3-dioxolan-2-one. Acta Crystallogr E Crystallogr Commun 73:1070-1072 |
| Huang, Qing; Quiñones, Edwin (2016) A spectroscopic method to determine the activity of the restriction endonuclease EcoRV that involves a single reaction. Anal Biochem 497:103-5 |
| Mège, Pascal; Schizas, Nikolaos V; Reyes, Joselyd García et al. (2015) Genetic seascape of the threatened Caribbean elkhorn coral, Acropora palmata, on the Puerto Rico Shelf. Mar Ecol (Berl) 36:195-209 |
| Morales-Rivera, Amarilys; Hernández-Burgos, Mayté M; Martínez-Rivera, Arlene et al. (2014) Anxiolytic effects of oxytocin in cue-induced cocaine seeking behavior in rats. Psychopharmacology (Berl) 231:4145-55 |
| Ramírez-Camejo, Luis A; Torres-Ocampo, Ana P; Agosto-Rivera, José L et al. (2014) An opportunistic human pathogen on the fly: strains of Aspergillus flavus vary in virulence in Drosophila melanogaster. Med Mycol 52:211-9 |
| Martínez-Rivera, Arlene; Rodríguez-Borrero, Enrique; Matías-Alemán, María et al. (2013) Metabotropic glutamate receptor 5 within nucleus accumbens shell modulates environment-elicited cocaine conditioning expression. Pharmacol Biochem Behav 110:154-60 |
| Galindo-Cardona, Alberto; Acevedo-Gonzalez, Jenny P; Rivera-Marchand, Bert et al. (2013) Genetic structure of the gentle Africanized honey bee population (gAHB) in Puerto Rico. BMC Genet 14:65 |
| Santiago-Rodriguez, Tasha M; Rivera, Jessica I; Coradin, Mariel et al. (2013) Antibiotic-resistance and virulence genes in Enterococcus isolated from tropical recreational waters. J Water Health 11:387-96 |
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