scholarly journals Chemoenzymatic synthesis of unmodified heparin oligosaccharides: cleavage of p-nitrophenyl glucuronide by alkaline and Smith degradation

2017 ◽  
Vol 15 (5) ◽  
pp. 1222-1227 ◽  
Author(s):  
Xing Zhang ◽  
Yongmei Xu ◽  
Po-Hung Hsieh ◽  
Jian Liu ◽  
Lei Lin ◽  
...  
Keyword(s):  
Chemoenzymatic Synthesis ◽  
Natural Structure ◽  
Smith Degradation ◽  
Heparin Oligosaccharides

A heparin oligosaccharide having a completely natural structure was successfully synthesized through a chemoenzymatic approach using an unnatural glycosyl acceptor, p-nitrophenyl glucuronide (GlcA-pNP).

scholarly journals Chemoenzymatic synthesis of heparan sulfate and heparin oligosaccharides and NMR analysis: paving the way to a diverse library for glycobiologists

2017 ◽  
Vol 8 (12) ◽  
pp. 7932-7940 ◽  
Author(s):  
Xing Zhang ◽  
Vijayakanth Pagadala ◽  
Hannah M. Jester ◽  
Andrew M. Lim ◽  
Truong Quang Pham ◽  
...  
Keyword(s):  
Heparan Sulfate ◽  
Chemoenzymatic Synthesis ◽  
Nmr Analysis ◽  
Heparin Oligosaccharides ◽  
The Way

A library of diverse heparan sulfate (HS) oligosaccharides was chemoenzymatically synthesized and systematically studied using NMR.

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.

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