| Reference | [1]. Org Biomol Chem. 2019 Feb 13;17(7):1634-1642. doi: 10.1039/c8ob02342e.<br />
The challenge of using isopropylamine as an amine donor in transaminase catalysed reactions.<br />
Kelefiotis-Stratidakis P(1), Tyrikos-Ergas T, Pavlidis IV.<br />
Author information: (1)Department of Chemistry, University of Crete, Voutes University Campus, 70013 Heraklion, Greece. [email protected].<br />
Amine transaminases (ATAs) propose an appealing alternative to transition metal catalysts as they can provide chiral amines of high purity from pro-chiral compounds by asymmetric synthesis. Industrial interest on ATAs arises from the fact that chiral amines are present in a wide spectrum of pharmaceutical and other high value-added chiral compounds and building blocks. Despite their potential as useful synthetic tools, several drawbacks such as challenges associated with the thermodynamic equilibrium can still impede their utilization. Several methods have been developed to displace the equilibrium, such as the use of alanine as an amine donor and the subsequent removal of pyruvate with a two-enzyme system, or the use of o-xylylene diamine. To date, the preferred amine donor remains isopropylamine (IPA), as the produced acetone can be removed easily under low pressure or slight heating, without complicating the process with other enzymes. Despite its small size, IPA is not widely accepted from wild-type ATAs, and this fact compromises its wide applicability. Herein, we index the reported biocatalytic aminations with IPA, comparing the sequences, while we discuss significant parameters of the process, such as the effect of temperature and pH, as well as the protein engineering and process development advances in the field. This information is expected to provide an insight for potential designs of tailor-made ATAs and IPA processes.<br />
DOI: 10.1039/c8ob02342e PMID: 30394478 [Indexed for MEDLINE]<br />
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[2]. Food Saf (Tokyo). 2019 Jun 28;7(2):54-55. doi: 10.14252/foodsafetyfscj.D-1900003. eCollection 2019 Jun.<br />
Isobutylamine, Isopropylamine, sec-Butylamine, Propylamine, Hexylamine, Pentylamine and 2-Methylbutylamine (Flavoring Substances).<br />
Food Safety Commission of Japan.<br />
Food Safety Commission of Japan (FSCJ) conducted risk assessments of isobutylamine, isopropylamine, sec-butylamine, propylamine, hexylamine, pentylamine and 2-methylbutylamine, which are used as food additives (flavors) (hereinafter, referred to as "the flavoring agents"), based on the Guidelines for the Assessment of Flavoring Substances in Foods on Health (Decision of the Commission Dated May 2016, hereinafter, referred to as the Guidelines on Flavoring Substances), using various documents. Based on the structural and metabolic similarity, FSCJ regarded that the identical procedures are applicable for the risk assessments of all the flavoring agents. FSCJ judged that the seven flavoring agents have no genotoxicities relevant to human health on the basis of the evaluation of analogous compounds. FSCJ metabolized to innocuous products with no food safety concerns. The estimated daily intakes of all the flavoring agents are within the range of 0.02 μg/person per day to 2 μg/person per day, which are below the threshold of concern (i.e., 1,800μg/person per day for Class I), and therefore, FSCJ judged that the flavoring agents are considered to be of no concern for food safety. In summary, FSCJ concluded, as a result of the safety assessment, that there is no safety concern with the flavoring agents, isobutylamine, isopropylamine, sec-butylamine, propylamine, hexylamine, pentylamine, and 2-methylbutylamine, as long as they are used as flavorings in foods.<br />
DOI: 10.14252/foodsafetyfscj.D-1900003 PMCID: PMC6978882 PMID: 31998587<br />
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[3]. Environ Sci Pollut Res Int. 2020 Jun;27(16):19298-19303. doi: 10.1007/s11356-020-07643-5. Epub 2020 Jan 20.<br />
Determination of acute oral toxicity of glyphosate isopropylamine salt in rats.<br />
Turkmen R(1), Dogan I(2).<br />
Author information: (1)Department of Pharmacology and Toxicology, Faculty of Veterinary Medicine, Afyon Kocatepe University, 03200, Afyonkarahisar, Turkey. [email protected]. (2)Department of Biostatistics, Faculty of Medicine, Gaziantep University, Gaziantep, Turkey.<br />
In this study, we aim to determine the median lethal dose (LD50) of glyphosate isopropylamine salt (GI), which is commonly used in the world and especially in Turkey against to weeds, in male and female rats by using the probit or logit analysis method. A total of 140 Wistar rats were used, including 70 females and 70 males. To determine LD50, the male and female rats were randomized into 7 groups made up of 10 animals in each group. At doses of 6000, 6500, 7000, 7500, 8000, 8500, and 9000 mg / kg, GI was administered to the male and female rats by oral gavage. After dosing, the animals were periodically monitored for 14 days. No deaths were observed after 48 h of herbicide application. In this study, only logit analysis was used for the LD50 value to be calculated in the male rats within 24 h, while other analyses were carried out with the probit method. In the female and male rats, the LD50 levels of GI between 24 and 48 h were determined as 7444.26-7878.50 mg/kg and 7203.58-7397.25 mg/kg, respectively. According to these results, it was concluded that female rats are more sensitive to GI than male rats. We believe that the findings that were obtained will guide researchers, clinicians, and toxicologists through preventive and curative studies against acute poisoning that may occur with GI.<br />
DOI: 10.1007/s11356-020-07643-5 PMID: 31960240 [Indexed for MEDLINE]<br />
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[4]. J Phys Chem A. 2020 Feb 20;124(7):1372-1381. doi: 10.1021/acs.jpca.9b11767. Epub 2020 Feb 11.<br />
Rich Collection of n-Propylamine and Isopropylamine Conformers: Rotational Fingerprints and State-of-the-Art Quantum Chemical Investigation.<br />
Melosso M(1), Melli A(1), Spada L(1)(2), Zheng Y(3), Chen J(3), Li M(3), Lu T(3), Feng G(3), Gou Q(3), Dore L(1), Barone V(2), Puzzarini C(1).<br />
Author information: (1)Dipartimento di Chimica "Giacomo Ciamician" , Università di Bologna , Via Selmi 2 , 40126 Bologna , Italy. (2)Scuola Normale Superiore , Piazza dei Cavalieri 7 , 56126 Pisa , Italy. (3)Department of Chemistry, School of Chemistry and Chemical Engineering , Chongqing University , Daxuecheng South Rd. 55 , 401331 Chongqing , China.<br />
The conformational isomerism of isopropylamine and n-propylamine has been investigated by means of an integrated strategy combining high-level quantum-chemical calculations and high-resolution rotational spectroscopy. The equilibrium structures (and thus equilibrium rotational constants) as well as relative energies of all conformers have been computed using the so-called "cheap" composite scheme, which combines the coupled-cluster methodology with second-order Møller-Plesset perturbation theory for extrapolation to the complete basis set. Methods rooted in the density functional theory have been instead employed for computing spectroscopic parameters and for accounting for vibrational effects. Guided by quantum-chemical predictions, the rotational spectra of isopropylamine and n-propylamine have been investigated between 2 and 400 GHz with Fourier transform microwave and frequency-modulation millimeter/submillimeter spectrometers. Spectral assignments confirmed the presence of several conformers with comparable stability and pointed out possible Coriolis resonance effects between some of them.<br />
DOI: 10.1021/acs.jpca.9b11767 PMCID: PMC7997563 PMID: 31985228<br />
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[5]. Ann Work Expo Health. 2018 May 28;62(5):633-638. doi: 10.1093/annweh/wxy010.<br />
Skin Notations for Low-Molecular-Weight Amines: Development of a Testing Protocol with Isopropylamine as an Example.<br />
Thredgold L(1), Gaskin S(1), Liu Y(1)(2), Heath L(1), Pisaniello D(1).<br />
Author information: (1)Occupational and Environmental Health, School of Public Health, University of Adelaide, South Australia, Australia. (2)College of Science and Technology, Hebei Agricultural University, Cangzhou, Hebei, China.<br />
Owing to their volatility, the most important occupational exposure route for low-molecular-weight amines is considered to be inhalation. However, dermal exposure is also possible in many workplace situations. There are limited data available on the dermal uptake of these amines through human skin, and existing exposure standard skin notations are typically based on acute toxicity animal studies or by chemical analogy. This gap in knowledge is in part due to a lack of standardized approach for assessing dermal uptake. We describe a relatively simple protocol for the determination of permeation of low-molecular-weight amines through human skin in vitro. Using isopropylamine as a test amine, it was found that isopropylamine vapour has limited capacity to absorb into, or penetrate through, the epidermal layer of human skin, even at lethal atmospheric concentrations. This protocol can be adapted for a range of exposure scenarios, including clothing effects, and may be used to determine whether skin notations are warranted.<br />
DOI: 10.1093/annweh/wxy010 PMID: 29846518
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