Ignacio Carrera

Ignacio Carrera
Universidad de la República de Uruguay | UdelaR · Facultad de Química

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41
Publications
4,541
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477
Citations
Citations since 2016
25 Research Items
289 Citations
20162017201820192020202120220102030405060
20162017201820192020202120220102030405060
20162017201820192020202120220102030405060
20162017201820192020202120220102030405060

Publications

Publications (41)
Article
This account describes the results of three decades of work on the production, chemistry, and synthetic applications of cis‐cyclohexadienediols obtained by biotransformation of arenes. These cis‐diols are valuable chiral building blocks, as they are enantiomerically pure, possessing good accessibility and high chemical versatility. Our work covers...
Article
Full-text available
Background Ayahuasca's psychological and subjective effects were compared in rituals of two neoshamanic groups in Uruguay. Aims Compare, describe and analyze psychological effects and subjective experiences of ayahuasca ceremonies in two different groups: a psychospiritual holistic center, and a center specialized in substance use disorder's treat...
Article
The current article presents a mixed qualitative-quantitative observational study of the effect of ayahuasca ritual on subjective experiences and personality traits on participants of a center specialized in the treatment of substance use disorder in Uruguay. When comparing the psychological traits of ayahuasca participants to a control group, quan...
Article
Full-text available
Ayahuasca is a psychedelic beverage originally from the Amazon rainforest used in different shamanic settings for medicinal, spiritual, and cultural purposes. It is prepared by boiling in water an admixture of the Amazonian vine Banisteriopsis caapi, which is a source of β-carboline alkaloids, with plants containing N,N-dimethyltryptamine, usually...
Article
Full-text available
The first stage of the drug discovery process involves the identification of small compounds with biological activity. Iboga alkaloids are monoterpene indole alkaloids (MIAs) containing a fused isoquinuclidine-tetrahydroazepine ring. Both the natural products and the iboga-inspired synthetic analogs have shown a wide variety of biological activitie...
Article
Allylic azides are a versatile structural motif in organic synthesis because the proximal double bond enables a [3,3]‐sigmatropic rearrangement, named as the Winstein rearrangement. In this manuscript an experimental and theoretical study on the double Winstein rearrangement occurring in azidodienediols derived from the biocatalytic dihydroxylation...
Article
Full-text available
Es posible desarrollar investigaciones clínicas utilizando sustancias psicodélicas en Uruguay? Resumen Los psicodélicos son sustancias capaces de alterar la conciencia, a través de su efecto sobre la transmisión serotoninérgica en el sistema nervioso central. En sus formas de ingesta tradicional son utilizados en rituales, con fines espirituales y...
Article
Full-text available
Iboga alkaloids are a group of monoterpenoid indole alkaloids with promising and intriguing biological activities. Ibogaine is the representative member of the series and has become widely known as a potent atypical psychedelic with promising effects to treat substance use disorder. Nowadays, an efficient and scalable enantioselective total synthes...
Article
Full-text available
Ibogaine is a psychedelic alkaloid that has attracted large scientific interest because of its antiaddictive properties in observational studies in humans as well as in animal models. Its subjective effect has been described as intense, vivid dream-like experiences occurring while awake; hence, ibogaine is often referred to as an oneirogenic psyche...
Article
We compared chemical profiles and in vitro biological activity of extracts obtained through maceration with ethanol or supercritical fluid extraction with CO2 (scCO2), from two different cannabis inflorescences chemotypes, one with high total tetrahydrocannabinol (THC) and other with high total cannabidiol (CBD) content. scCO2 was performed to obta...
Preprint
Full-text available
Ibogaine is a psychedelic alkaloid that has attracted scientific interest because of its important antiaddictive properties evidenced in observational studies in humans, and in models for substance-use-disorders in rodents. Its subjective effect has been described as intense vivid dream-like experiences occurring while awake; hence, ibogaine is oft...
Article
Full-text available
Anecdotal reports and open label case studies in humans indicated that the psychedelic alkaloid ibogaine exerts profound anti-addictive effects. Ample preclinical evidence demonstrated the efficacy of ibogaine, and its main metabolite noribogaine, in substance use disorder rodent models. In contrast to addiction research, depression-relevant effect...
Preprint
Anecdotal reports and open label case studies in humans indicated that the psychedelic alkaloid ibogaine exert profound anti-addictive effects. Ample preclinical evidence demonstrated the efficacy of ibogaine, and its main metabolite noribogaine, in substance use disorder rodent models. In contrast to addiction research, depression-relevant effects...
Article
Expanding the reaction scope of natural metalloenzymes can provide new opportunities for biocatalysis. Mononuclear non‐heme iron‐dependent enzymes represent a large class of biological catalysts involved in the biosynthesis of natural products and catabolism of xenobiotics, among other processes. Here, we report that several members of this enzyme...
Article
Full-text available
Ibogaine is an atypical psychedelic alkaloid, which has been subject of research due to its reported ability to attenuate drug-seeking behavior. Recent work has suggested that ibogaine effects on alcohol self-administration in rats are related to the release of Glial cell Derived Neurotrophic Factor (GDNF) in the Ventral Tegmental Area (VTA), a mes...
Preprint
Full-text available
p>Ibogaine is a psychedelic alkaloid which has been subject of intense scientific research due to its reported ability to attenuate drug-seeking behavior. Recent work suggested that ibogaine effects on alcohol self-administration in rats was related to the release of Glial Cell Derived Neurotrophic Factor (GDNF) in the Ventral Tegmental Area (VTA),...
Article
Full-text available
Ibogaine is a potent psychedelic alkaloid that has been the focus of intense research because of its intriguing anti-addictive properties. According to anecdotic reports, ibogaine has been originally classified as an oneirogenic psychedelic; i.e., induces a dream-like cognitive activity while awake. However, the effects of ibogaine administration o...
Article
Full-text available
A new mononuclear complex of zinc(II), [Zn(HL)2]∙2DMF (H2L = (E)-N’-((E)-(hydroxyimino)butan-2-ylidene)salicyloylhydrazide, DMF = N,N-dimethylformamide), was prepared and characterized. Single crystal X-ray crystallography revealed a six-coordinate zinc(II) surrounded by nitrogen of the oxime function and oxygen and distal nitrogens of the acylhydr...
Article
Toluene Dioxygenase (TDO) enzymatic complex has been widely used as a biocatalyst for the regio- and enantioselective preparation of cis-cyclohexadienediols, which are very important starting materials for organic synthesis. However, the lack of regio- and stereodiversity of the dioxygenation process by TDO and related dioxygenases constitutes a cl...
Article
The enantioselective preparation of three protected β-amino- γ -hydroxyesters from benzoic acid is described. The employed synthetic methodology involves the ipso, ortho cis-dihydroxylation of benzoic acid by the mutant strain Ralstonia eutropha B9, followed by a selective halonium induced beta lactamization. Modification of this novel β-lactam str...
Article
Toluene Dioxygenase (TDO) enzymatic complex has been widely used for preparation of enantiopure cis-cyclohexadienediols for synthetic applications. Along the last 30 years, a variety of mono- and di-substituted arenes have been studied as substrates for this enzyme, and some interesting observations have been reported regarding the yield and select...
Article
The synthesis, crystal structures and luminescence of a novel family of lanthanide polymer complexes with general formula [Ln2(Hmidp)3(H2O)3](ClO4)3·6H2O (Ln = Nd, Sm, Eu, Gd, Dy, Ho, Tm; H2midp = N-methyliminodipropionic acid) are reported. The compounds were obtained by direct reaction of H2midp and lanthanide(III) perchlorate in aqueous solution...
Article
A facile and short chemoenzymatic synthesis of (-) 1L-5-amino-5-deoxy-allo-inositol hexaacetate is described using benzyl azide as starting material. The key transformations consist of an enzymatic dioxygenation using the toluene dioxygenase enzymatic complex, followed by an allylic azide double sigmatropic [3,3] shift to introduce the nitrogen fun...
Article
Enzymatic dioxygenation of benzyl azide by Toluene Dioxygenase (TDO) produces significant amounts of the cis-cyclohexadienediol derived from benzonitrile along with the expected azido diols. In this manuscript we demonstrate that TDO catalyses the enzymatic oxidation of benzyl azide to benzonitrile which is further dioxygenated to produce the obser...
Article
Aza and oxo Diels-Alder reactions using enantiopure cis-cyclohexadienediols were studied. These dienediols were obtained from the biotransformation of monosubstituted arenes using bacterial dioxygenases (toluene and benzoate dioxygenases). Ethyl glyoxylate and its N-tosyl imine were used as dienophiles to afford the corresponding hetero Diels-Alder...
Article
Full-text available
Enzymatic dioxygenation of benzyl azide by toluene dioxygenase produces the expected enantiopure cis-cyclohexadienediol along with an exocyclic diene formed by a spontaneous sequence of two [3,3] sigmatropic shifts. This novel dienediol presents high synthetic potential for natural product synthesis. The sigmatropic rearrangements can be reversed b...
Article
Stereoselective hydrogenation of methylcyclohex-2-ene-1,4-diols used as important intermediates for the preparation of ampelomins and deoxy-carbasugars was studied. These olefins were obtained in few steps from a chiral cis-diol resulting from microbial oxidation of toluene. Although the stereoselective hydrogenation of this type of substrates is d...
Article
A chemoenzymatic synthesis of an enantiopure 6-substituted 5,6-dihydro-2H-pyran-2-one using bromobenzene as a starting material is presented. This important structural motif is found in a large number of chiral lactones that present a wide range of biological activities. The key features of the preparation include enzymatic dioxygenation of bromobe...
Article
Chiral cis-1,2-dihydrocatechols have been extensively used as starting materials for the synthesis of complex organic molecules. The preparation of these high added value compounds is carried out mainly by enzymatic dihydroxylation of arenes since no other efficient chemical method is known. In this paper we describe a detailed study of the biotech...
Article
Full-text available
Crocidosema (= Epinotia) aporema (Walsingham) (Lepidoptera: Tortricidae) is a bud borer that feeds on soybean and forage legumes. Its economic importance is restricted to South America, where it can alternate throughout the year between forage and grain legumes. The sex pheromone of C. aporema females is composed of a 15:1 mixture of (7Z,9Z)-dodeca...
Article
We here report a study of the intramolecular amination of sp(3) C-H bonds via the hydride transfer cyclization of N-tosylimines (HT-amination). In this transformation, 5-aryl aldehydes are subjected to N-toluenesulfonamide in the presence of BF(3)·OEt(2) to effect imine formation and HT-cyclization, leading to 2-arylpiperidines and 3-aryl-1,2,3,4-t...
Article
Four generations of chemoenzymatic approaches to oseltamivir are presented. The first two generations relied on the use of cyclohexadiene-cis-diol derived enzymatically from bromobenzene. The third and fourth generation used the corresponding diol obtained from ethyl benzoate by fermentation with E. coli JM109(pDTG601a). Oseltamivir was obtained fr...
Article
The oxidative C–C cleavage of α-hydroxy ketones was found to proceed smoothly in solvent-free, silica-supported sodium metaperiodate, under microwave irradiation. This provides a useful and green synthetic procedure to form the corresponding carboxylic acid and aldehyde in good yields, avoiding the solubility problems of the sodium metaperiodate in...
Article
A screening of 15 fungi and yeast strains was carried out in fermentation processes to perform the diastereo- and enantioselective reduction of ethyl 2-methyl-3-oxobutanoate, to the corresponding (R∗,S∗)-3-hydroxy-2-methyl esters. Overall, biotransformations led to excellent conversions, as well as good to excellent diastereo- and enantioselectivit...
Article
A short chemoenzymatic formal synthesis of oseltamivir from ethyl benzoate has been achieved. The key steps involve a toluene dioxygenase-mediated dihydroxylation, hetero-Diels-Alder cycloaddition, and generation of C4 acetamido functionality. The formal synthesis of oseltamivir is achieved in ten steps and incorporates a unique translocation of th...
Article
The halohydroxylation of a number of cyclohexadienediol derivatives has been investigated. The selectivity of the reaction as a function of the type of substituent on the diene, protecting group of the diol functionality, halonium donor, medium polarity, and temperature is described. Best selectivity is obtained for iodohydrin formation. The course...
Article
A new simple method for catalyzed iodohydroxylation of alkenes using stoichiometric amounts of water is described. The iodohydrins were prepared in good yields from the corresponding alkenes using N-iodosuccinimide, 2equiv of H2O, and catalytic amounts of diphenyl diselenide in MeCN.

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