scholarly journals Biphenyl dioxygenase-catalysed cis-dihydroxylation of tricyclic azaarenes: chemoenzymatic synthesis of arene oxide metabolites and furoquinoline alkaloids

RSC Advances ◽  
2013 ◽  
Vol 3 (27) ◽  
pp. 10944 ◽  
Author(s):  
Derek R. Boyd ◽  
Narain D. Sharma ◽  
Jonathan G. Carroll ◽  
Pui L. Loke ◽  
Colin R. O'Dowd ◽  
...  
Keyword(s):  
Chemoenzymatic Synthesis ◽  
Biphenyl Dioxygenase ◽  
Arene Oxide

scholarly journals Toluene Dioxygenase-Catalyzed cis-Dihydroxylation of Quinolines: A Molecular Docking Study and Chemoenzymatic Synthesis of Quinoline Arene Oxides

2021 ◽  
Vol 8 ◽  
Author(s):  
Derek R. Boyd ◽  
Narain D. Sharma ◽  
Pui L. Loke ◽  
Jonathan G. Carroll ◽  
Paul J. Stevenson ◽  
...  
Keyword(s):  
Molecular Docking ◽  
Docking Study ◽  
Docking Studies ◽  
Chemoenzymatic Synthesis ◽  
Autodock Vina ◽  
Molecular Docking Study ◽  
Toluene Dioxygenase ◽  
Arene Oxide ◽  
Carbocyclic Rings ◽  
Derivatives Of

Molecular docking studies of quinoline and 2-chloroquinoline substrates at the active site of toluene dioxygenase (TDO), were conducted using Autodock Vina, to identify novel edge-to-face interactions and to rationalize the observed stereoselective cis-dihydroxylation of carbocyclic rings and formation of isolable cis-dihydrodiol metabolites. These in silico docking results of quinoline and pyridine substrates, with TDO, also provided support for the postulated cis-dihydroxylation of electron-deficient pyridyl rings, to give transient cis-dihydrodiol intermediates and the derived hydroxyquinolines. 2-Chloroquinoline cis-dihydrodiol metabolites were used as precursors in the chemoenzymatic synthesis of enantiopure arene oxide and arene dioxide derivatives of quinoline, in the context of its possible mammalian metabolism and carcinogenicity.

A One-Pot Chemoenzymatic Synthesis of (2S,4R)-4-Methylproline Enables the First Total Synthesis of Antiviral Lipopeptide Cavinafungin B

2018 ◽  
Author(s):  
Christian R. Zwick ◽  
Hans Renata
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Complex Molecule ◽  
Molecular Target ◽  
Chemoenzymatic Synthesis ◽  
General Strategy ◽  
One Pot

We report an efficient ten-step synthesis of antiviral natural product cavinafungin B in 37% overall yield. By leveraging a one-pot chemoenzymatic synthesis of (2S,4R)-4-methylproline and oxazolidine-tethered (Rink-Boc-ATG-resin) SPPS methodology, the assembly of our molecular target could be conducted in an efficient manner.This general strategy could prove amenable to the construction of other natural and unnatural linear lipopeptides. The value of incorporating biocatalytic steps in complex molecule synthesis is highlighted by this work.

scholarly journals Recent Advances in the Chemical Biology of N-Glycans

Molecules ◽  
2021 ◽  
Vol 26 (4) ◽  
pp. 1040
Author(s):  
Asuka Shirakawa ◽  
Yoshiyuki Manabe ◽  
Koichi Fukase
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Molecular Basis ◽  
Chemical Biology ◽  
Molecular Level ◽  
Chemoenzymatic Synthesis ◽  
Complex Structures ◽  
Recent Advances ◽  
Protein Functions ◽  
Potential Applications

Asparagine-linked N-glycans on proteins have diverse structures, and their functions vary according to their structures. In recent years, it has become possible to obtain high quantities of N-glycans via isolation and chemical/enzymatic/chemoenzymatic synthesis. This has allowed for progress in the elucidation of N-glycan functions at the molecular level. Interaction analyses with lectins by glycan arrays or nuclear magnetic resonance (NMR) using various N-glycans have revealed the molecular basis for the recognition of complex structures of N-glycans. Preparation of proteins modified with homogeneous N-glycans revealed the influence of N-glycan modifications on protein functions. Furthermore, N-glycans have potential applications in drug development. This review discusses recent advances in the chemical biology of N-glycans.

scholarly journals Machine‐Driven Chemoenzymatic Synthesis of Glycopeptide

2020 ◽  
Vol 59 (45) ◽  
pp. 19825-19829
Author(s):  
Jiabin Zhang ◽  
Ding Liu ◽  
Varma Saikam ◽  
Madhusudhan R. Gadi ◽  
Christopher Gibbons ◽  
...  
Keyword(s):  
Chemoenzymatic Synthesis

scholarly journals Chemoenzymatic synthesis of complex N‐glycans of the parasite S.mansoni to examine the importance of epitope presentation on DC‐SIGN recognition

2021 ◽  
Author(s):  
Apoorva D. Srivastava ◽  
Luca Unione ◽  
Mehman Bunyatov ◽  
Ivan A. Gagarinov ◽  
Nicola G. A. Abrescia ◽  
...  
Keyword(s):  
Chemoenzymatic Synthesis ◽  
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