63526-71-6Relevant articles and documents
Rapid transformation of sulfinate salts into sulfonates promoted by a hypervalent iodine(III) reagent
Deruer, Elsa,Hamel, Vincent,Blais, Samuel,Canesi, Sylvain
supporting information, p. 1203 - 1207 (2018/06/04)
An alternative method for forming sulfonates through hypervalent iodine(III) reagent-mediated oxidation of sodium sulfinates has been developed. This transformation involves trapping reactive sulfonium species using alcohols. With additional optimization of the reaction conditions, the method appears extendable to other nucleophiles such as electron-rich aromatic systems or cyclic ethers through a ring opening pathway.
Long-Chain Alkyl Cyanides: Unprecedented Volatile Compounds Released by Pseudomonas and Micromonospora Bacteria
Montes Vidal, Diogo,von Rymon-Lipinski, Anna-Lena,Ravella, Srinivasa,Groenhagen, Ulrike,Herrmann, Jennifer,Zaburannyi, Nestor,Zarbin, Paulo H. G.,Varadarajan, Adithi R.,Ahrens, Christian H.,Weisskopf, Laure,Müller, Rolf,Schulz, Stefan
supporting information, p. 4342 - 4346 (2017/04/03)
The analysis of volatiles from bacterial cultures revealed long-chain aliphatic nitriles, a new class of natural products. Such nitriles are produced by both Gram-positive Micromonospora echinospora and Gram-negative Pseudomonas veronii bacteria, although the structures differ. A variable sequence of chain elongation and dehydration in the fatty acid biosynthesis leads to either unbranched saturated or unsaturated nitriles with an ω?7 double bond, such as (Z)-11-octadecenenitrile, or methyl-branched unsaturated nitriles with the double bond located at C-3, such as (Z)-13-methyltetradec-3-enenitrile. The nitrile biosynthesis starts from fatty acids, which are converted into their amides and finally dehydrated. The structures and biosyntheses of the 19 naturally occurring compounds were elucidated by mass spectrometry, synthesis, and feeding experiments with deuterium-labeled precursors. Some of the nitriles showed antimicrobial activity, for example, against multiresistant Staphylococcus aureus strains.
Macrolides and alcohols as scent gland constituents of the Madagascan frog mantidactylus femoralis and their intraspecific diversity
Poth, Dennis,Peram, Pardha Saradhi,Vences, Miguel,Schulz, Stefan
supporting information, p. 1548 - 1558 (2013/10/22)
Acoustic and, to a lesser degree, visual signals are the predominant means of signaling in frogs. Nevertheless, certain lineages such as the mantelline frogs from Madagascar use the chemical communication channel as well. Males possess femoral glands on the hind legs, which recently have been shown to contain volatile compounds used in communication as pheromones. Many mantelline species occur in sympatry, and so far species recognition is regarded to occur mainly by acoustic signals. The analysis of the gland constituents of Mantidactylus femoralis by GC/MS revealed the presence of volatile macrolides and secondary alcohols. The new natural products mantidactolides A (4) and B (6), as well as several methyl carbinols, were identified, and their structures were confirmed by synthesis. The analysis of individuals from different locations of Madagascar revealed the presence of two groups characterized by specific patterns of compounds. While one group contained the alcohols and mantidactolide B, the other showed specific presence of the macrolides phoracantholide I (1) and mantidactolide A (4). Genetic analysis of some individuals showed no congruence between genetic relatedness and gland constituents. Several other individuals from related species had different gland compositions. This suggests that a basic set of biosynthetic machinery might be available to a broader group of related species.
