27198-63-6Relevant academic research and scientific papers
Antibody-catalyzed formation of a 14-membered ring lactone
Pungente, Michael D.,Weiler, Larry,Ziltener, Hermann J.
, p. 1643 - 1645 (2007/10/03)
Monoclonal antibody (MAb) F123, raised against a macrocyclic phosphonate transition-state analogue, catalyzed an intramolecular transesterification of the corresponding hydroxy ester to give a 14-membered ring lactone. The MAb reaction displayed enzyme-like Michaelis-Menten kinetics with a Km of 255 μM and a kcat of 0.01 min-1 based on p-nitrophenol release and calculated on an active-site basis. Substrate specificity and competitive inhibition by a transition state analogue (Ki = 3 μM) demonstrated that the catalytic activity was associated with binding in the anti-body-combining site. The lactone product was isolated from a large-scale catalytic experiment through ether extraction and identified by gas chromatography - mass spectroscopy.
ACTIVATED CARBOXYLATES FROM THE PHOTOOXYGENATION OF OXAZOLES. APPLICATION TO THE SYNTHESIS OF RECIFEIOLIDE AND OTHER MACROCYCLIC LACTONES.
Wasserman, Harry H.,Gambale, Ronald J.,Pulwer, Mitchell J.
, p. 1737 - 1740 (2007/10/02)
The oxazole system may serve as a protecting group for the carboxyl function.The carboxylate is generated under mild conditions of photooxygenation in high yield in the form of the reactive triamide.This reaction has been applied to the synthesis of macrocyclic lactones.
