An Approach to the Precise Chemoenzymatic Synthesis of13C-Labeled Sialyloligosaccharide on an Intact Glycoprotein:  A Novel One-Pot [3-13C]-Labeling Method for Sialic Acid Analogues by Control of the Reversible Aldolase Reaction, Enzymatic Synthesis of [3-13C]-NeuAc-α-(2→3)-[U-13C]-Gal-β-(1→4)-GlcNAc-β- Sequence onto Glycoprotein, and Its Conformational Analysis by Developed NMR Techniques

2000 ◽  
Vol 122 (24) ◽  
pp. 5678-5694 ◽  
Author(s):  
Tatsuo Miyazaki ◽  
Hajime Sato ◽  
Tohru Sakakibara ◽  
Yasuhiro Kajihara
Keyword(s):  
Sialic Acid ◽  
Conformational Analysis ◽  
Enzymatic Synthesis ◽  
Chemoenzymatic Synthesis ◽  
One Pot ◽  
13C Labeling ◽  
Sialic Acid Analogues ◽  
Nmr Techniques ◽  
Labeling Method

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

scholarly journals One-pot multi-enzyme (OPME) chemoenzymatic synthesis of sialyl-Tn-MUC1 and sialyl-T-MUC1 glycopeptides containing natural or non-natural sialic acid

2013 ◽  
Vol 21 (16) ◽  
pp. 4778-4785 ◽  
Author(s):  
Hamed Malekan ◽  
Gabriel Fung ◽  
Vireak Thon ◽  
Zahra Khedri ◽  
Hai Yu ◽  
...  
Keyword(s):  
Sialic Acid ◽  
Chemoenzymatic Synthesis ◽  
One Pot ◽  
Sialyl Tn

scholarly journals Effective one-pot multienzyme (OPME) synthesis of monotreme milk oligosaccharides and other sialosides containing 4-O-acetyl sialic acid

2016 ◽  
Vol 14 (36) ◽  
pp. 8586-8597 ◽  
Author(s):  
Hai Yu ◽  
Jie Zeng ◽  
Yanhong Li ◽  
Vireak Thon ◽  
Baojun Shi ◽  
...  
Keyword(s):  
Sialic Acid ◽  
Chemoenzymatic Synthesis ◽  
Milk Oligosaccharides ◽  
One Pot

Chemoenzymatic synthesis: Monotreme milk glycans and other sialosides containing a 4-O-acetyl-sialic acid were synthesized in a gram or preparative scales using a one-pot two-enzyme sialylation system containing bacterial CMP-sialic acid synthetase and sialyltransferase PmST3.

One-Pot Synthesis and Conformational Analysis of 6-Membered Cyclic Iodonium Salts

2020 ◽  
Author(s):  
Lucien Caspers ◽  
Julian Spils ◽  
Mattis Damrath ◽  
Enno Lork ◽  
Boris Nachtsheim
Keyword(s):  
Conformational Analysis ◽  
Bronsted Acids ◽  
One Pot ◽  
Benzyl Alcohols ◽  
Iodonium Salts ◽  
Efficient Approach ◽  
One Pot Synthesis ◽  
Diaryliodonium Salts

In this article we describe an efficient approach for the synthesis of cyclic diaryliodonium salts. The method is based on benzyl alcohols as starting materials and consists of an Friedel-Crafts-arylation/oxidation sequence. Besides a deep optimization, particluar focusing on the choice and ratios of the utilized Bronsted-acids and oxidants, we explore the substrate scope of this transformation. We also discuss an interesting isomerism of cyclic iodonium salts substituted with aliphatic substituents at the bridge head carbon. <br>

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.

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