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.
Phosphine-Catalyzed (4+1) Annulation: Rearrangement of Allenylic Carbamates to 3-Pyrrolines through Phosphonium Diene Intermediates
Blank, Brian R.,Andrews, Ian P.,Kwon, Ohyun
, p. 4352 - 4372 (2020/08/05)
We have developed a phosphine-catalyzed (4+1) annulative rearrangement for the preparation of 3-pyrrolines from allenylic carbamates via phosphonium diene intermediates. We employed this methodology to synthesize an array of 1,3-disubstituted- and 1,2,3-t
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
