Mechanistic Studies on Pyridoxal Phosphate Synthase:  The Reaction Pathway Leading to a Chromophoric Intermediate

2008 ◽  
Vol 130 (10) ◽  
pp. 3043-3052 ◽  
Author(s):  
Jeremiah W. Hanes ◽  
Kristin E. Burns ◽  
David G. Hilmey ◽  
Abhishek Chatterjee ◽  
Pieter C. Dorrestein ◽  
...  
Keyword(s):  
Pyridoxal Phosphate ◽  
Reaction Pathway ◽  
Mechanistic Studies ◽  
Phosphate Synthase

13C NMR snapshots of the complex reaction coordinate of pyridoxal phosphate synthase

2008 ◽  
Vol 4 (7) ◽  
pp. 425-430 ◽  
Author(s):  
Jeremiah W Hanes ◽  
Ivan Keresztes ◽  
Tadhg P Begley
Keyword(s):  
13C Nmr ◽  
Pyridoxal Phosphate ◽  
Reaction Coordinate ◽  
Complex Reaction ◽  
Phosphate Synthase

scholarly journals Manganese-mediated reductive functionalization of activated aliphatic acids and primary amines

2020 ◽  
Vol 11 (1) ◽  
Author(s):  
Zhan Li ◽  
Ke-Feng Wang ◽  
Xin Zhao ◽  
Huihui Ti ◽  
Xu-Ge Liu ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Late Stage ◽  
Materials Science ◽  
Reaction Pathway ◽  
Chemical Conversion ◽  
Primary Amines ◽  
Mechanistic Studies ◽  
Reaction Conditions ◽  
Aliphatic Acids ◽  
Redox Active

Abstract Alkyl carboxylic acids as well as primary amines are ubiquitous in all facets of biological science, pharmaceutical science, chemical science and materials science. By chemical conversion to redox-active esters (RAE) and Katritzky’s N-alkylpyridinium salts, respectively, alkyl carboxylic acids and primary amines serve as ideal starting materials to forge new connections. In this work, a Mn-mediated reductive decarboxylative/deaminative functionalization of activated aliphatic acids and primary amines is disclosed. A series of C-X (X = S, Se, Te, H, P) and C-C bonds are efficiently constructed under simple and mild reaction conditions. The protocol is applicable to the late-stage modification of some structurally complex natural products or drugs. Preliminary mechanistic studies suggest the involvement of radicals in the reaction pathway.

scholarly journals Site-Fixed Hydroboration of Alkenes under Metal-Free Conditions: Scope and Mechanistic Studies

2021 ◽  
Author(s):  
Sida Li ◽  
Chenyang Hu ◽  
Xin Cui ◽  
Liu Leo Liu ◽  
Lipeng Wu
Keyword(s):  
Reaction Pathway ◽  
Original Position ◽  
Side Reactions ◽  
Single Electron Transfer ◽  
Mechanistic Studies ◽  
Radical Species ◽  
Metal Free ◽  
Proton Source ◽  
Alkene Oligomerization ◽  
Metal Catalyzed

An unprecedented and general metal-free hydroboration of alkenes with BBr3 as the boration reagent in the presence of iPr2NEt is reported. The addition of iPr2NEt not only suppresses alkene oligomerization and bromoboration side reactions, but also provides a proton source for hydroboration. More importantly, the site-fixed installation of a boryl group at the original position of the internal double-bond is easily achieved using our strategy as compared with traditional transition-metal-catalyzed hydroboration processes. Preliminary studies on the mechanism revealed a distinct reaction pathway that involves radical species and may operate through frustrated-Lewispair-type single-electron transfer.

Mechanistic studies on the pyridoxal phosphate enzyme 1-aminocyclopropane-1-carboxylate deaminase from Pseudomonas sp

Biochemistry ◽  
1981 ◽  
Vol 20 (26) ◽  
pp. 7509-7519 ◽  
Author(s):  
Christopher Walsh ◽  
Robert A. Pascal ◽  
Michael Johnston ◽  
Ronald Raines ◽  
Dinesh Dikshit ◽  
...  
Keyword(s):  
Pyridoxal Phosphate ◽  
Pseudomonas Sp ◽  
Mechanistic Studies

scholarly journals A metal-free approach for the hydrogenolysis of unactivated C(aryl)–C(alkyl) bonds

2021 ◽  
Author(s):  
Huadong Wang ◽  
Yuliang Xu ◽  
Yizhou Yang ◽  
Yizhen Liu ◽  
Zhen Li
Keyword(s):  
Heterogeneous Catalysts ◽  
Reaction Pathway ◽  
Petroleum Industry ◽  
Transition Metal Catalysts ◽  
Waste Plastics ◽  
Mechanistic Studies ◽  
Synergistic Activation ◽  
Synthetic Utility ◽  
Selective Hydrogenolysis ◽  
Opening Up

Abstract The hydrogenolysis of C–C bonds is among one of the most important processes in the petroleum industry which has been considered as a viable way to recycle waste polyolefins. These transformations typically rely on heterogeneous catalysts and take place at high temperature and high pressure with limited selectivity. Employing homogenous transition metal catalysts, while allowing the hydrogenolysis of C–C bonds to proceed under much milder conditions, is only suitable for substrates containing strained C–C bonds or directing groups. Here we report that a borenium complex can catalyze the selective hydrogenolysis of unstrained C(aryl)–C(alkyl) bonds of alkylarenes at ambient temperature, affording the corresponding alkanes and arenes. This method does not require the assistance of directing groups, and tolerates a range of functional groups. Mechanistic studies suggest a reaction pathway that involves a synergistic activation of dihydrogen by the borenium complex and alkylarenes, followed by retro-Friedel-Crafts reaction to cleave the C(aryl)–C(alkyl) bonds. The synthetic utility of this protocol was demonstrated by the conversion of post-consumer polystyrene into valuable benzene and phenylalkanes with mass recovery above 90%, thus opening up new avenues for the recycling of aromatic chemicals from waste plastics.

Structural and Thermodynamic Insights into the Assembly of the Heteromeric Pyridoxal Phosphate Synthase from Plasmodium falciparum

2007 ◽  
Vol 374 (3) ◽  
pp. 732-748 ◽  
Author(s):  
Karlheinz Flicker ◽  
Martina Neuwirth ◽  
Marco Strohmeier ◽  
Barbara Kappes ◽  
Ivo Tews ◽  
...  
Keyword(s):  
Plasmodium Falciparum ◽  
Pyridoxal Phosphate ◽  
Phosphate Synthase

scholarly journals Mechanistic Studies of 1-Deoxy-D-Xylulose-5-Phosphate Synthase from Deinococcus radiodurans

2018 ◽  
Vol 04 (01) ◽  
Author(s):  
Sumit Handa ◽  
Daniel R Dempsey ◽  
Divya Ramamoorthy ◽  
Nanci Cook ◽  
Wayne C Guida ◽  
...  
Keyword(s):  
Deinococcus Radiodurans ◽  
Mechanistic Studies ◽  
Phosphate Synthase

scholarly journals Doubly Decarboxylative Synthesis of 4-(Pyridylmethyl)chroman-2-ones and 2-(Pyridylmethyl)chroman-4-ones under Mild Reaction Conditions

Molecules ◽  
2021 ◽  
Vol 26 (15) ◽  
pp. 4689
Author(s):  
Jan Bojanowski ◽  
Anna Albrecht
Keyword(s):  
Carboxylic Acids ◽  
Reaction Pathway ◽  
Base Catalysis ◽  
Mechanistic Studies ◽  
Reaction Conditions ◽  
Michael Type Addition ◽  
Brønsted Base

The doubly decarboxylative Michael–type addition of pyridylacetic acid to chromone-3-carboxylic acids or coumarin-3-carboxylic acids has been developed. This protocol has been realized under Brønsted base catalysis, providing biologically interesting 4-(pyridylmethyl)chroman-2-ones and 2-(pyridylmethyl)chroman-4-ones in good or very good yields. The decarboxylative reaction pathway has been confirmed by mechanistic studies. Moreover, attempts to develop an enantioselective variant of the cascade are also described.

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