scholarly journals Chemoenzymatic synthesis of α-dystroglycan core M1 O-mannose glycans

2015 ◽  
Vol 51 (58) ◽  
pp. 11654-11657 ◽  
Author(s):  
Yan Zhang ◽  
Caicai Meng ◽  
Lan Jin ◽  
Xi Chen ◽  
Fengshan Wang ◽  
...  
Keyword(s):  
Chemoenzymatic Synthesis ◽  
One Pot ◽  
Preparative Scale

A diversity-oriented chemoenzymatic synthesis of α-dystroglycan (α-DG) core M1 O-mannose glycans at the preparative scale via sequential one-pot multienzyme (OPME) glycosylation of a chemically prepared disaccharyl serine intermediate was reported.

scholarly journals Synthesis of Ribavirin, Tecadenoson, and Cladribine by Enzymatic Transglycosylation

Catalysts ◽  
2019 ◽  
Vol 9 (4) ◽  
pp. 355 ◽  
Author(s):  
Marco Rabuffetti ◽  
Teodora Bavaro ◽  
Riccardo Semproli ◽  
Giulia Cattaneo ◽  
Michela Massone ◽  
...  
Keyword(s):  
Aeromonas Hydrophila ◽  
Purine Nucleoside Phosphorylase ◽  
Chemoenzymatic Synthesis ◽  
Nucleoside Analogues ◽  
Specific Substrate ◽  
One Pot ◽  
Preparative Scale ◽  
Heterocyclic Base ◽  
Novel Approach ◽  
New Synthesis

Despite the impressive progress in nucleoside chemistry to date, the synthesis of nucleoside analogues is still a challenge. Chemoenzymatic synthesis has been proven to overcome most of the constraints of conventional nucleoside chemistry. A purine nucleoside phosphorylase from Aeromonas hydrophila (AhPNP) has been used herein to catalyze the synthesis of Ribavirin, Tecadenoson, and Cladribine, by a “one-pot, one-enzyme” transglycosylation, which is the transfer of the carbohydrate moiety from a nucleoside donor to a heterocyclic base. As the sugar donor, 7-methylguanosine iodide and its 2′-deoxy counterpart were synthesized and incubated either with the “purine-like” base or the modified purine of the three selected APIs. Good conversions (49–67%) were achieved in all cases under screening conditions. Following this synthetic scheme, 7-methylguanine arabinoside iodide was also prepared with the purpose to synthesize the antiviral Vidarabine by a novel approach. However, in this case, neither the phosphorolysis of the sugar donor, nor the transglycosylation reaction were observed. This study was enlarged to two other ribonucleosides structurally related to Ribavirin and Tecadenoson, namely, Acadesine, or AICAR, and 2-chloro-N6-cyclopentyladenosine, or CCPA. Only the formation of CCPA was observed (52%). This study paves the way for the development of a new synthesis of the target APIs at a preparative scale. Furthermore, the screening herein reported contributes to the collection of new data about the specific substrate requirements of AhPNP.

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.

One-Pot Chemoenzymatic Synthesis of 3‘-Functionalized Cephalosporines (Cefazolin) by Three Consecutive Biotransformations in Fully Aqueous Medium

1997 ◽  
Vol 62 (26) ◽  
pp. 9099-9106 ◽  
Author(s):  
O. H. Jústiz ◽  
R. Fernández-Lafuente ◽  
J. M. Guisán ◽  
P. Negri ◽  
G. Pagani ◽  
...  
Keyword(s):  
Aqueous Medium ◽  
Chemoenzymatic Synthesis ◽  
One Pot

Chiral (R)- and (S)-allylic alcohols via a one-pot chemoenzymatic synthesis

2007 ◽  
Vol 18 (23) ◽  
pp. 2791-2796 ◽  
Author(s):  
Simona Sgalla ◽  
Giancarlo Fabrizi ◽  
Roberto Cirilli ◽  
Alberto Macone ◽  
Alessandra Bonamore ◽  
...  
Keyword(s):  
Chemoenzymatic Synthesis ◽  
Allylic Alcohols ◽  
One Pot

Chemoenzymatic Synthesis of Ubiquitous Biological Redox Cofactors

Synlett ◽  
2017 ◽  
Vol 28 (10) ◽  
pp. 1151-1159 ◽  
Author(s):  
Amnon Kohen ◽  
Priyanka Singh ◽  
Qi Guo
Keyword(s):  
Nicotinamide Adenine Dinucleotide ◽  
Enzymatic Synthesis ◽  
Metabolic Enzymes ◽  
Chemoenzymatic Synthesis ◽  
Nicotinamide Adenine ◽  
General Strategy ◽  
One Pot ◽  
Post Translational Modifications ◽  
One Step ◽  
Methylene Tetrahydrofolate

Redox cofactors are utilized by a myriad of proteins, ranging from metabolic enzymes to those performing post-translational modifications. Labeled redox cofactors have served as a vital tool for a broad range of studies. This account describes chemoenzymatic syntheses of the isotopically labeled, biologically important redox cofactors: nicotinamide adenine dinucleotide, methylene tetrahydrofolate, and flavin nucleotides. An overview of the general strategy is presented. These examples demonstrate the utility of enzymatic synthesis.1 Introduction2 Nicotinamide Cofactors2.1 Synthesis of Remote-Labeled 14C-NADPH2.1.1 Synthesis of [Ad-14C]NADPH2.1.2 Synthesis of [Carbonyl-14C]NADPH2.2 Synthesis of S- and R-[4-3H]NADPH2.2.1 One-Step S- and Three-Step R-[4-3H]NADPH Synthesis2.2.2 One-Pot, One-Step R-[4-3H]NADPH Synthesis2.3 Synthesis of S- and R-[Ad-14C, 4-2H]NADPH2.3.1 One-Step S-, Three-Step R-[Ad-14C, 4-2H]NADPH Synthesis2.3.2 One-Pot, One-Step R-[Ad-14C, 4-2H]NADPH Synthesis3 Methylene Tetrahydrofolate4 Flavin Nucleotides5 Conclusions and Outlook

Sign in / Sign up

Export Citation Format

Share Document