MS/NMR:  A Structure-Based Approach for Discovering Protein Ligands and for Drug Design by Coupling Size Exclusion Chromatography, Mass Spectrometry, and Nuclear Magnetic Resonance Spectroscopy

2001 ◽  
Vol 73 (3) ◽  
pp. 571-581 ◽  
Author(s):  
Franklin J. Moy ◽  
Kevin Haraki ◽  
Dominick Mobilio ◽  
Gary Walker ◽  
Robert Powers ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Drug Design ◽  
Magnetic Resonance Spectroscopy ◽  
Nuclear Magnetic Resonance Spectroscopy ◽  
Size Exclusion ◽  
Resonance Spectroscopy ◽  
Protein Ligands ◽  
Exclusion Chromatography

scholarly journals N,N-Bis(Hexyl α-d-Acetylmannosyl) Acrylamide

Molbank ◽  
10.3390/m1255 ◽  
2021 ◽  
Vol 2021 (3) ◽  
pp. M1255
Author(s):  
Atsushi Miyagawa ◽  
Shinya Ohno ◽  
Hatsuo Yamamura
Keyword(s):  
Mass Spectrometry ◽  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Magnetic Resonance Spectroscopy ◽  
Nuclear Magnetic Resonance Spectroscopy ◽  
Side Reaction ◽  
Resonance Spectroscopy ◽  
Biological Functions ◽  
Unknown Compound ◽  
Acrylamide Monomer

Glycosyl monomers for the assembly of multivalent ligands are typically synthesized using carbohydrates with biological functions and polymerizable functional groups such as acrylamide or styrene introduced into the carbohydrate aglycon, and monomers polymerized using a radical initiator. Herein, we report the acryloylation of 6-aminohexyl α-mannoside and its conversion into the glycosyl monomer bearing an acrylamide group. The general acryloylation procedure afforded the desired N-hexyl acetylmannosyl acrylamide monomer as well as an unexpected compound with a close Rf value. The compounds were separated and analyzed by nuclear magnetic resonance spectroscopy and mass spectrometry, which revealed the unknown compound to be the bivalent N,N-bis(hexyl α-d-acetylmannosyl) acrylamide monomer, which contains two hexyl mannose units and one acrylamide group. To the best of our knowledge, this side reaction has not previously been disclosed, and may be useful for the construction of multivalent sugar ligands.

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