Synthesis of Regio- and Stereospecifically Deuterium Labelled 2-Benzylindanes
نویسنده
چکیده
2-Benzylindenes (1, la ) are hydrogenated to 2-benzylindanes (2) using tris-(triphenylphosphine)-rhodium(I)-chloride in benzene by a strict cis-1,2 addition of hydrogen to the double bond. Thus, stereoand regio-specific deuterium labelling at the five-membered ring of various 2-benzylindanes has been carried out. The high selectivity of deuterium incorporation is shown independently by 'H NM R and mass (M IKE*) spectrometry of selected 2-benzylindanes.
منابع مشابه
Synthesis of backbone deuterium labelled [r(CGCGAAUUCGCG)]2 and HPLC purification of synthetic RNA.
The chemical synthesis of backbone deuterium labelled [r(CGCGAAU*U*CGCG)]2 (U* = [5'-2H]U) is described. An efficient purification procedure was developed using a polymeric reverse phase (PRP) HPLC column at 60 degrees C. This procedure provided pure RNA dodecamer in the multi-milligram quantities (39% overall yield) necessary for dynamics studies using solid-state deuterium NMR. The purificati...
متن کاملUse of inhibitors to study reactions catalyzed by enzymes requiring pyridoxal phosphate as coenzyme*
The stereochemistry of a variety of pyridoxal phosphate-mediated enzymic reactions has been studied using enzyme inhibitors that are stereospecifically labeled in the b-position with deuterium. A versatile synthesis has been developed to prepare a wide variety of stereospecifically labeled Dand L-amino acids and inhibitors. Investigation of the “turnover” of b-chloro-D-alanine and Dand L-serine...
متن کاملStereospecificity of Cinnamyl Alcohol Dehydrogenase and Synthesis of Stereospecifically Labelled Coniferyl Alcohol
Using horse liver alcohol dehydrogenase, stereospecifically tritiated (R)and (S)-(y-3H)-coniferyl alcohol was synthesized. Using both of these substrates it was demonstrated that cinnamyl alcohol dehydrogenase from lignifying Forsythia tissue specifically removes the pro-R-hydrogen atom of coniferyl alcohol in the oxidation to the aldehyde. This also means that in the reverse reaction the A-hyd...
متن کاملThe Use of 13C in the Synthesis of Double Labelled Precursors
Discovery of 13C NMR and its application in the biosynthetic pathways prompted the synthesis of several 13C labelled precursors. To investigate the metabolism of phenyllactic acid in the Solanaceae family, the double labelled acid was synthesized from barium carbonate (13C) and sodium syanide (13C)
متن کاملStereochemistry of 2-phenylethylamine oxidation catalyzed by bacterial copper amine oxidase.
The stereochemical course of the reaction catalyzed by a copper amine oxidase from Arthrobacter globiformis has been investigated using 2-phenylethylamine stereospecifically deuterium-labeled at the C1 position. Measurements of deuterium content in the product, phenylacetaldehyde, by gas chromatography-mass spectrometry revealed stereospecific abstraction of the pro-S hydrogen during the enzyma...
متن کامل