10138-10-0Relevant articles and documents
Thomas,Aue
, p. 1807,1808 (1973)
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Wermuth
, p. 2406,2407, 2408 (1979)
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Rationalizing the Origin of Solerone (5-Oxo-4-hexanolide): Biomimetic Synthesis and Identification of Key Metabolites in Sherry Wine
Haering, Dietmar,Schreier, Peter,Herderich, Markus
, p. 369 - 372 (1997)
A biomimetic synthesis of solerone (5-oxo-4-hexanolide, 1) using both enzymatic and acid-catalyzed reactions was performed. Starting from L-glutamic acid 5-ethyl ester (2) enzymatic oxidative deamination followed by subsequent decarboxylation of the corresponding 2-oxoglutaric acid 5-ethyl ester (3) led to ethyl 4-oxobutanoate (4). In the presence of pyruvate, 4 served as key substrate for a novel acyloin condensation catalyzed by pyruvate decarboxylase (EC 4.1.1.1) from Saccharomyces cerevisiae. Finally, the resulting ethyl 4-hydroxy-5-oxo-hexanoate (5) was easily converted into solerone (1) in the presence of acid. The acyloin condensation of 3 with acetaldehyde to ethyl 5-hydroxy-4-oxohexanoate (6) revealed an alternative route to solerone (1). Acid-catalyzed lactonization of 6 produced 4-oxo-5-hexanolide (7) as well as 5 and 1 via keto-enol tautomerization. Confirming the relevance of the proposed biogenetic pathway, the solerone precursors 2-6 as well as δ-lactone 7 were identified in sherry by GC/MS analysis for the first time.
Takegami et al.
, p. 1456 (1967)
Synthesis and Characterization of Novel Acyl-Glycine Inhibitors of GlyT2
Mostyn, Shannon N.,Carland, Jane E.,Shimmon, Susan,Ryan, Renae M.,Rawling, Tristan,Vandenberg, Robert J.
, p. 1949 - 1959 (2017)
It has been demonstrated previously that the endogenous compound N-arachidonyl-glycine inhibits the glycine transporter GlyT2, stimulates glycinergic neurotransmission, and provides analgesia in animal models of neuropathic and inflammatory pain. However, it is a relatively weak inhibitor with an IC50 of 9 μM and is subject to oxidation via cyclooxygenase, limiting its therapeutic value. In this paper we describe the synthesis and testing of a novel series of monounsaturated C18 and C16 acyl-glycine molecules as inhibitors of the glycine transporter GlyT2. We demonstrate that they are up to 28 fold more potent that N-arachidonyl-glycine with no activity at the closely related GlyT1 transporter at concentrations up to 30 μM. This novel class of compounds show considerable promise as a first generation of GlyT2 transport inhibitors.
Binuclear Pd(I)-Pd(I) Catalysis Assisted by Iodide Ligands for Selective Hydroformylation of Alkenes and Alkynes
Zhang, Yang,Torker, Sebastian,Sigrist, Michel,Bregovi?, Nikola,Dydio, Pawe?
supporting information, p. 18251 - 18265 (2020/11/02)
Since its discovery in 1938, hydroformylation has been thoroughly investigated and broadly applied in industry (>107 metric ton yearly). However, the ability to precisely control its regioselectivity with well-established Rh- or Co-catalysts has thus far proven elusive, thereby limiting access to many synthetically valuable aldehydes. Pd-catalysts represent an appealing alternative, yet their use remains sparse due to undesired side-processes. Here, we report a highly selective and exceptionally active catalyst system that is driven by a novel activation strategy and features a unique Pd(I)-Pd(I) mechanism, involving an iodide-assisted binuclear step to release the product. This method enables β-selective hydroformylation of a large range of alkenes and alkynes, including sensitive starting materials. Its utility is demonstrated in the synthesis of antiobesity drug Rimonabant and anti-HIV agent PNU-32945. In a broader context, the new mechanistic understanding enables the development of other carbonylation reactions of high importance to chemical industry.
PROTEIN KINASE C AGONISTS
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Paragraph 0337, (2020/09/12)
The present disclosure relates generally to certain diacylglycerol lactone compounds, pharmaceutical compositions comprising said compounds, and methods of making and using said compounds and pharmaceutical compositions. The compounds and compositions dis