10017-08-0Relevant articles and documents
Synthesis of α,β-unsaturated (S)-cyanohydrins using the oxynitrilase from Hevea brasiliensis
Klempier,Pichler,Griengl
, p. 845 - 848 (1995)
α,β-unsaturated (S)-cyanohydrins derived from 2-propenal, 2-butenal, (E) and (Z)-2-hexenal and 2-hexynal are obtained in high enantiomeric purity (80-95%, e.e.) by using an oxynitrilase isolated from the leaves of Hevea brasiliensis.
Asymmetric synthesis of tetronic acids by Blaise reaction of protected optically active cyanohydrins
Duffield, Jonathan J.,Regan, Andrew C.
, p. 663 - 666 (1996)
An asymmetric synthesis of tetronic acids is described, involving the Blaise reaction of Reformatsky reagents with silyl-protected optically active cyanohydrins, which were prepared by an enzyme-catalysed method.
Triazole Ureas Act as Diacylglycerol Lipase Inhibitors and Prevent Fasting-Induced Refeeding
Deng, Hui,Kooijman, Sander,Van Den Nieuwendijk, Adrianus M. C. H.,Ogasawara, Daisuke,Van der Wel, Tom,Van Dalen, Floris,Baggelaar, Marc P.,Janssen, Freek J.,Van Den Berg, Richard J. B. H. N.,Den Dulk, Hans,Cravatt, Benjamin F.,Overkleeft, Herman S.,Rensen, Patrick C. N.,Van der Stelt, Mario
, p. 428 - 440 (2017/04/26)
Triazole ureas constitute a versatile class of irreversible inhibitors that target serine hydrolases in both cells and animal models. We have previously reported that triazole ureas can act as selective and CNS-active inhibitors for diacylglycerol lipases (DAGLs), enzymes responsible for the biosynthesis of 2-arachidonoylglycerol (2-AG) that activates cannabinoid CB1 receptor. Here, we report the enantio- and diastereoselective synthesis and structure-activity relationship studies. We found that 2,4-substituted triazole ureas with a biphenylmethanol group provided the most optimal scaffold. Introduction of a chiral ether substituent on the 5-position of the piperidine ring provided ultrapotent inhibitor 38 (DH376) with picomolar activity. Compound 38 temporarily reduces fasting-induced refeeding of mice, thereby emulating the effect of cannabinoid CB1-receptor inverse agonists. This was mirrored by 39 (DO34) but also by the negative control compound 40 (DO53) (which does not inhibit DAGL), which indicates the triazole ureas may affect the energy balance in mice through multiple molecular targets.
Synthesis of eight 1-deoxynojirimycin isomers from a single chiral cyanohydrin
Van Den Nieuwendijk, Adrianus M.C.H.,Van Den Berg, Richard J.B H.N.,Ruben, Mark,Witte, Martin D.,Brussee, Johannes,Boot, Rolf G.,Van Der Marel, Gijsbert A.,Aerts, Johannes M.F.G.,Overkleeft, Herman S.
scheme or table, p. 3437 - 3446 (2012/08/27)
Eight configurational 1-deoxynojirimycin isomers have been synthesized starting from a chiral cyanohydrin as the common precursor. The cyanohydrin chiral pool building block is easily accessible in large quantities by using almond hydroxynitrile lyase as the chiral catalyst in condensing hydrogen cyanide and crotonaldehyde. Our work complements the large body of literature on the synthesis of 1-deoxynojirimycin derivatives with the distinguishing feature that eight stereoisomers of this important class of glycosidase inhibitors can be derived from a common precursor in an efficient manner.
Chiral linear polymers bonded alternatively with salen and 1,4-dialkoxybenzene: Synthesis and application for Ti-catalyzed asymmetric TMSCN addition to aldehydes
Sakthivel, Sekarpandi,Punniyamurthy, Tharmalingam
experimental part, p. 2834 - 2840 (2011/03/19)
The synthesis of chiral linear polymers 1a-b having salen and 1,4-dioctyloxybenzene as alternate segments has been accomplished. The GPC analysis showed the molecular weights corresponding to ca. 15 (Mw = 10,999, Mn = 9165 and PDI = 1.20) repeating units for 1a and ca. 8 (Mw = 8547, Mn = 7883 and PDI = 1.08) repeating units for 1b. Polymers 1a-b have been studied with Ti(OiPr)4 as a recyclable catalyst for the asymmetric addition of TMSCN to aldehydes while the selectivity of the polymer catalyst is identical to that of the monomer. The reactions are efficient affording the cyanohydrins with up to 88% ee. The selectivity of the polymer based catalyst 9a is found to be the same to that of the monomer 10a. The reaction provides the advantages of simplified product isolation and easy recovery and recyclability of polymer catalyst 9a without any loss of activity or selectivity.
