93598-34-6Relevant academic research and scientific papers
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.
Indole cleavage with mebhydroline by sodium periodate - Part 2. Mechanism of the dilactam formation
Moehrle,Rohn,Westle
, p. 391 - 399 (2007/10/03)
The γ-carbolines 1a-d reacted with periodate by loss of one carbon - without available precursors - to the eight-membered dilactams 3a-c and the amino acid 9d. As possible intermediates of an indole cleavage α-aminoketones as models were examined. While the oxidation of chain-formed 13 afforded only a small amount of C-lost amide 23, the cyclic species 24 and 32 gave rise to considerably higher yields of the corresponding lactams 29 and 36. From the benzazepinone 32 with Hg(II)-EDTA the intermediate product 43, containing all genuine C-atoms, was formed, which could quantitatively cleaved by periodate to the lactam 36 and formic acid. This mechanism can be transferred to the reactions of the γ-carbolines 1a-d.
Reduction and carboxylation of 1-chloromethyl-6,7-dimethoxy-3,4-dihydroisoquinolinLum salts. An easy entry to 1-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline alkaloids
Suau, Rafael,Ruiz, Inmaculada,Posadas, Natalia,Valpuesta, Maria
, p. 545 - 550 (2007/10/03)
At 25°C, the NaBH4/MeOH reduction of the title isoquinolinium salts gave the aziridine exclusively. At a low temperature (0°C) in the presence of CO2/K2CO3, the 2-oxazolidinone was obtained in almost quantitative yield. Controlled hydrolysis of the borane complex derived from the isoquinolinium salts also gave the cyclic carbamate. (±)-Calycotomine and its N-Me derivative were obtained in high yields.
A Ring Destruction Approach To Some Benzo-Fused Medium-Sized Heterocycles by Means of Cyanogen Bromide under Solvolytic Conditions. X-Ray Structure of a 1H-2,6-Benzoxazecine-6-Carbonitrile and a 2H-3,6-Benzoxazecine-6-Carbonitrile Derivative
Bremner, John B.,Raston, Colin L.,Rowbottom, Graham L.,White, Allan H.,Winzenberg, Kevin N.
, p. 893 - 912 (2007/10/02)
Reaction of the reduced pyrroloisoquinoline amine (1a) with cyanogen bromide in the presence of methanol gave the medium-ring cyanamide derivative 7,9,10-trimethoxy-2,3,4,5,6,7-hexahydro-1H-3-benzazonine-3-carbonitrile (2a).Analogous products were also obtained from reaction of the reduced 5H-oxazoloisoquinoline, 2H-benzoquinolizine, 2H,6H-oxazinoisoguinoline and oxazinoisoquinoline derivatives (1b-e), whereas the reduced 3H-oxazoloisoguinoline and 5H-oxazoloisoquioline derivatives (1f) and (8) gave 1-(2,4-dioxapentyl>-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-2-carbonitrile (5a) andN--N-methylcyanamide (9) respectively, the latter in low yield.The medium-sized heterocyclic derivatives (2f-h) were also obtained from cyanogen bromide-mediated water solvolysis reaction of (1a), (1c) and (1e).The cyanamides (2a-h), (5a) and (9) have been converted into the respective tertiary amine derivatives (3a-h), (5c) and (11), with concomitant reduction of the carbonyl group in the last case.The crystal and molecular structure of 1,10,11-trimethoxy-3,4,5,6,7,8-hexahydro-1H-2,6-benzoxazecine-6-carbonitrile (2d) and 1-hydroxy-10,11-dimethoxy-1,4,5,6,7,8-hexahydro-2H-3,6-benzoxazecine-6-carbonitrile (2h) have been determined by single-crystal X-ray methods.
A NEW GENERATION OF α-OXA-ACYLIMINIUM IONS AND AN APPLICATION TO A SYNTHESIS OF OXAZOLOISOQUINOLINE AND RELATED COMPOUNDS
Kano, Shinzo,Yuasa, Yoko,Yokomatsu, Tsutomu,Shibuya, Shiroshi
, p. 1475 - 1476 (2007/10/02)
The carbamates, obtained by the reaction of the azide with ethyl glycolate and ethyl lactate, were reduced with i-Bu2AlH and the reduction products were treated with formic acid to give the corresponding oxazoloisoquinolines.By this method, the thi
