The Isolation and Identification of Piperidine-2-Carboxylic Acid in the Urine of Protein Malnourished Rats

1971 ◽  
Vol 41 (6) ◽  
pp. 535-543
Author(s):  
R. S. Crowne ◽  
C. Donninger ◽  
R. F. Grimble ◽  
R. G. Whitehead
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Liquid Chromatography ◽  
Carboxylic Acid ◽  
Magnetic Resonance ◽  
Ion Exchange ◽  
Magnetic Resonance Spectroscopy ◽  
Resonance Spectroscopy ◽  
Gas Liquid Chromatography ◽  
Isolation And Identification ◽  
Unknown Compound

1. A previously unidentified compound first observed in the serum of children with kwashiorkor has been isolated from the urine of experimental protein malnourished rats. 2. On mass spectroscopy and nuclear-magnetic-resonance spectroscopy the unknown compound appeared identical with authentic piperidine-2-carboxylic acid. This identity was confirmed by the behaviour of the unknown and authentic compounds on paper, ion-exchange, thin-layer or gas-liquid chromatography. 3. The significance of the accumulation of piperidine-2-carboxylic acid in the serum of children with kwashiorkor is discussed.

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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