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Principles of Chemistry
Published in Arthur T. Johnson, Biology for Engineers, 2019
Phosphate groups are not the only energy-rich chemical compounds used by living systems. Sulfur can also form high-energy bonds as part of thioesters. Sulfur was probably prevalent in the prebiotic Earth, and was probably used by the most ancient of organisms to provide energy for life (de Duve, 1995). Even today, there are primitive life forms that surround sources of sulfur-containing gases from deep within the Earth and use these gases as their primary energy sources (see Sections 6 [BRIC], 6.2 [Oxygen], and 6.5.1 [Heat Sources]).
The Prelude of Green Syntheses of Drugs and Natural Products
Published in Ahindra Nag, Greener Synthesis of Organic Compounds, Drugs and Natural Products, 2022
Leonardo Xochicale-Santana, C. C. Vidyasagar, Blanca M. Muñoz-Flores, Víctor M. Jiménez Pérez
Thioesters are a functional group that is found in a great variety of organic compounds, this since the structure is used for the construction of heterocyclic compounds for the development of thio drugs with pharmaceutical importance.47,48 However, there are very few reports for the synthesis of these compounds by ultrasound; one among one of them was reported by Siqueira and co-workers49; they describe a rapid method for the synthesis of thiols from mercaptobenzooxazole and benzoyl chloride, in excellent yields and short reaction times in comparison with conventional thermal methods (Scheme 15.16).
Metabolic Engineering for the Production of a Variety of Biofuels and Biochemicals
Published in Kazuyuki Shimizu, Metabolic Regulation and Metabolic Engineering for Biofuel and Biochemical Production, 2017
The fatty acid synthesis is made from AcCoA in the main metabolism, and produces fatty acyl-ACP (acyl carrier protein), which is directed cellular components such as structural and storage lipids. The fatty acid-derived chemicals are formed from thioesters (in fatty acid synthesis), fatty acyl-CoA thioesters (in fatty acid catabolism), or free fatty acids (from thioesterase) of cleavage of acyl-thioesters (Lennen and Pfleger 2013).
Copper-Catalyzed direct thioetherification of Alkyl Halides with S-Alkyl Butanethioate as Thiol transfer reagent
Published in Journal of Sulfur Chemistry, 2022
Qingqiang Tian, Lili Wang, Yahui Li
As de Duvewrites wrote in a ‘Thioester World": thioesters are possible precursors to life. Thioesters are important intermediates in many biosynthetic reactions. Compared with thiols, the direct use of simple thioesters as a sulfur source is more attractive. However, to our knowledge, the utility of simple thioesters as coupling partners in the formation of alkyl sulfides has been seldomly studied [38]. In addition, S-alkyl butanethioateis stable, has low toxicity, and is far less odorous than a typical thiol. Given the above and as part of our ongoing research on the new sulfur reagents in 2020, our group reported a Pd-catalyzed thiolation of aryl iodides and S-alkyl butanethioate. Based on our continuous interest in metal-catalyzed C–S bond formation (Scheme 2, D) [39] we describe herein a new and efficient method for the formation of alkyl sulfides by reacting alkyl halides with S-alkyl butanethioate in the presence of IPrCuCl as a catalyst.
Methods for the direct synthesis of thioesters from aldehydes: a focus review
Published in Journal of Sulfur Chemistry, 2020
Noor H. Jabarullah, Kittisak Jermsittiparsert, Pavel A. Melnikov, Andino Maseleno, Akram Hosseinian, Esmail Vessally
The main synthetic method for the synthesis of thioesters involves the thioesterification reactions of carbonyl compounds (e.g. carboxylic acids, acid anhydrides, acyl chlorides, aldehydes) with thiol sources. In 2015, in an article entitled ‘thioesters synthesis: recent adventures in the esterification of thiols', Kazemi and Shiri [9] summarized the available literature on these reactions, however, preparation of thioesters from aldehydes was omitted. Very recently, Fleischer and co-workers [10] in their interesting review article highlighted the oxidative coupling of aldehydes and thiols, albeit in a small paragraph. Since a number of advances and developments in the direct thioesterification of aldehydes have occurred from 1976 to present, a comprehensive review on this interesting research topic seems to be timely. In connection with our review articles on the formation of C–S bonds [11–22] and new methodologies in organic synthesis [23–35], in this Focus-Review, we will highlight recent progress on direct thioesterification of aldehydes with various thiol sources (Figure 1), with special attention on the mechanistic aspects of the reactions. The cross-dehydrogenative coupling reactions of aldehydes with thiols are discussed first. This is followed by cross-coupling of aldehydes with disulfides and thioesterification with ArSO2SRf reagents. Finally, some miscellaneous reactions will be covered at the end of the review.