53558-94-4Relevant articles and documents
MICROBIAL TRANSFORMATION OF (-)-VERNOLIC ACID INTO (4R,5R)-5-HYDROXY-γ-DECALACTONE
Albrecht, Wolfgang,Tressl, Roland
, p. 1391 - 1396 (1993)
(-)-Vernolic acid, isolated and purified from seeds of Euphorbia lagascae was administered to cultures of Sporobolomyces odorus. (4R,5R)-5-Hydroxy-γ-decalactone 1 accumulated as the main product.The configuration of the product was determined by synthesis of all four stereoisomers and comparison of spectroscopic and chromatographic data.
On the thermodynamic equilibrium between (R)-2-hydroxyacyl-CoA and 2-enoyl-CoA
Parthasarathy, Anutthaman,Buckel, Wolfgang,Smith, David M.
experimental part, p. 1738 - 1746 (2011/04/18)
A combined experimental and computational approach has been applied to investigate the equilibria between several α-hydroxyacyl-CoA compounds and their 2-enoyl-CoA derivatives. In contrast to those of their β, γ and α counterparts, the equilibria for the α-compounds are relatively poorly characterized, but qualitatively they appear to be unusually sensitive to substituents. Using a variety of techniques, we have succeeded in measuring the equilibrium constants for the reactions beginning from 2-hydroxyglutaryl-CoA and lactyl-CoA. A complementary computational evaluation of the equilibrium constants shows quantitative agreement with the measured values. By examining the computational results, we arrive at an explanation of the substituent sensitivity and provide a prediction for the, as yet unmeasured, equilibrium involving 2-hydroxyisocaproyl-CoA.
Total synthesis and structural confirmation of (+)-longicin
Hanessian, Stephen,Giroux, Simon,Buffat, Maxime
, p. 3989 - 3992 (2007/10/03)
(Chemical Equation Presented) A stereocontrolled total synthesis of (+)-longicin, a representative of the class of mono-THF-acetogenins, is described. The strategy involves the utilization of D- and L-glutamic acids as chirons that correspond to two five-carbon segments harboring stereogenic centers at C4 and at C17 of the C32 polyketide-derived natural product. The use of Grubbs' RCM reaction as a novel "chain elongation" strategy for the synthesis of acetogenin-type structures and a new protocol for butenolide incorporation are also described.
