39066-05-2Relevant articles and documents
Structure and Biocatalytic Scope of Coclaurine N-Methyltransferase
Bennett, Matthew R.,Thompson, Mark L.,Shepherd, Sarah A.,Dunstan, Mark S.,Herbert, Abigail J.,Smith, Duncan R. M.,Cronin, Victoria A.,Menon, Binuraj R. K.,Levy, Colin,Micklefield, Jason
supporting information, p. 10600 - 10604 (2018/08/17)
Benzylisoquinoline alkaloids (BIAs) are a structurally diverse family of plant secondary metabolites, which have been exploited to develop analgesics, antibiotics, antitumor agents, and other therapeutic agents. Biosynthesis of BIAs proceeds via a common pathway from tyrosine to (S)-reticulene at which point the pathway diverges. Coclaurine N-methyltransferase (CNMT) is a key enzyme in the pathway to (S)-reticulene, installing the N-methyl substituent that is essential for the bioactivity of many BIAs. In this paper, we describe the first crystal structure of CNMT which, along with mutagenesis studies, defines the enzymes active site architecture. The specificity of CNMT was also explored with a range of natural and synthetic substrates as well as co-factor analogues. Knowledge from this study could be used to generate improved CNMT variants required to produce BIAs or synthetic derivatives.
Enantioselective nickel-catalyzed hydrocyanation of vinylarenes using chiral phosphine-phosphite ligands and TMS-CN as a source of HCN
Falk, Anna,Goederz, Anna-Lena,Schmalz, Hans-Guenther
supporting information, p. 1576 - 1580 (2013/03/13)
Anti-headache chemistry: In the presence of a tailored modular P,P ligand the nickel-catalyzed addition of HCN, generated in situ from TMS-CN, to styrene derivatives proceeds with an unprecedented level of stereocontrol (up to 97 % ee) to give 2-aryl-acetonitriles, for example, the depicted precursor of Ibuprofen. Copyright
COPPER(I) IODIDE-MEDIATED ARYLATION OF DIALKYL CYANOMETHANEPHOSPHONATES. A NOVEL ROUTE TO α-ARYLATED ALKANENITRILES
Suzuki, Hitomi,Watanabe, Kazue,Qui, Yi
, p. 1779 - 1780 (2007/10/02)
Copper(I)-catalyzed arylation of dialkyl cyanomethanephosphonate anions in hot hexamethylphosphoric triamide affords α-arylalkanenitriles in moderate to good yields.
