97549-54-7Relevant 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.
Pictet-Spengler reaction of biogenic amines with (2R)-N- glyoxyloylbornane-10,2-sultam. Enantioselective synthesis of (S)-(+)-N- methylcalycotomine and (R)-(+)-xylopinine
Czarnocki, Zbigniew,Arazny, Zbigniew
, p. 2871 - 2879 (2007/10/03)
The Pictet-Spengler reaction of (2R)-N-glyoxyloylbornane-10,2-sultam with dopamine hydrochloride gave the condensation product, which was further converted into (S)-(+)-N)-methylcalycotomine and (R)-(+)-xylopinine of high enantiomeric purity.
Pictet-Spengler reaction of biogenic amines with (2R)-N-glyoxyloylbornane-10,2-sultam. Enantioselective synthesis of (S)-(+)-N-methylcalycotomine
Czarnocki,Mieczkowski,Kiegiel,Arazny
, p. 2899 - 2902 (2007/10/03)
(2R)-N-glyoxyloylbornane-10,2-sultam reacted with dopamine hydrochloride, forming the Pictet-Spengler condensation product, which was further converted into (S)-(+)-N-methylcalycotomine of high enantiomeric purity. The same kind of reaction with tryptamine hydrochloride gave the condensation product with 100% d.e.