794513-01-2Relevant articles and documents
IspG converts an epoxide substrate analogue to (E)-4-hydroxy-3-methylbut-2- enyl diphosphate: Implications for IspG catalysis in isoprenoid biosynthesis
Nyland II, Rodney L.,Xiao, Youli,Liu, Pinghua,Freel Meyers, Caren L.
supporting information; experimental part, p. 17734 - 17735 (2010/04/01)
(Chemical Equation Presented) IspG is an intriguing enzyme in bacteria, parasite, and plant isoprenoid biosynthesis, and its catalytic mechanism remains elusive. We report here the synthesis of (2R,3R)-4-hydroxy-3-methyl-2,3- epoxybutanyl diphosphate (Epoxy-HMBPP), a proposed intermediate in one of the frequently cited mechanistic models. We have also demonstrated that this epoxide analogue is a catalytically competent IspG substrate. This study represents the first mechanistic study of this important enzyme.
Synthesis of diastereomerically and enantiomerically pure 2,3-disubstituted tetrahydrofurans using a sulfoxonium ylide
Schomaker, Jennifer M.,Pulgam, Veera Reddy,Borhan, Babak
, p. 13600 - 13601 (2007/10/03)
Nucleophilic substitution reactions of 2,3-epoxy alcohols, easily prepared via Sharpless asymmetric epoxidation chemistry, offer access to a wide variety of enantiomerically pure compounds. In this communication, we describe the use of a Payne rearrangement to control regioselectivity in the ring-opening of a series of 2,3-epoxy alcohols with dimethylsulfoxonium methylide to yield diastereomerically and/or enantiomerically pure disubstituted tetrahydrofuran rings. The factors influencing the success and substitution pattern of the THF ring products are discussed, including steric, electronic, and solvent effects. Copyright
Convergent enantioselective synthesis of the tricyclic core of phomactin A
Mohr, Peter J.,Halcomb, Randall L.
, p. 2413 - 2416 (2007/10/03)
(Matrix Presented) The tricyclic core of phomactin A was synthesized from 6,6-dimethyl-2-cyclohexen-1-one. Key reactions include the addition of a cyclohexenyllithium reagent to an epoxyaldehyde and a regioselective intramolecular epoxide opening to insta
Simple and versatile synthesis of branched polyols: (+)-2-C-methylerythritol and (+)-2-C-methylthreitol
Fontana,Messina,Spinella,Cimino
, p. 7559 - 7562 (2007/10/03)
The paper reports a new approach for the enantioselective synthesis of 2-C-methyl tetrols. The procedure has been utilized for preparing methylthreitol and methylerythritol, a putative intermediate in the mevalonate-independent biosynthesis of terpenoids in bacteria, algae and higher plants. The methodology offers straightforward access to related compounds and isotopically labeled derivatives. (C) 2000 Elsevier Science Ltd.
Construction of a Chiral Quaternary Carbon Center via 1,2-Acyl Migration of an Optically Active α,β-Epoxy Ketone
Okada, Kunisuke,Katsura, Toshiyuki,Tanino, Hideo,Kakoi, Hisae,Inoue, Shoji
, p. 157 - 160 (2007/10/02)
The construction of a chiral building block with a quaternary carbon center is described, based on the Lewis acid-catalyzed acyl migration of α,β-epoxy ketone with alkyl and alkenyl substituents.
