Sugar Oxazolines as Directly Preparable Glycosyl Donors from Unprotected N-Acetyl-2-Amino Sugars: Towards One-Pot Chemoenzymatic Synthesis of Glycoproteins Catalyzed by N-Acetylglucosaminidases

2014 ◽  
pp. 1-6
Author(s):  
Shin-ichiro Shoda ◽  
Atsushi Kobayashi ◽  
Masato Noguchi
Keyword(s):  
Chemoenzymatic Synthesis ◽  
Amino Sugars ◽  
One Pot ◽  
Glycosyl Donors

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.

Conformationally armed glycosyl donors: reactivity quantification, new donors and one pot reactions

2008 ◽  
pp. 2465 ◽  
Author(s):  
Christian Marcus Pedersen ◽  
Lavinia G. Marinescu ◽  
Mikael Bols
Keyword(s):  
One Pot ◽  
New Donors ◽  
Glycosyl Donors

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

Substoichiometric FeCl3 Activation of Propargyl Glycosides for the Synthesis of Disaccharides and Glycoconjugates

Synlett ◽  
2018 ◽  
Vol 29 (05) ◽  
pp. 668-672 ◽  
Author(s):  
Jianbo Zhang ◽  
Guosheng Sun ◽  
Yue Wu ◽  
Anqi Liu ◽  
Saifeng Qiu ◽  
...  
Keyword(s):  
Reaction Conditions ◽  
One Pot ◽  
One Pot Synthesis ◽  
Optimal Reaction ◽  
Glycosyl Donors

Glycosides as glycosyl donors using FeCl3 have been described. Under optimal reaction conditions, three kinds of propargyl glycosides were found to react with steroids and sugar-derived glycosyl acceptors to afford the corresponding disaccharides and glycoconjugates in good to excellent yields (66–91%). Meanwhile, the method can also realize one-pot synthesis of disaccharides, making it an effective, affordable, and green glycosylation procedure.

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