The Tohoku Journal of Experimental Medicine
Online ISSN : 1349-3329
Print ISSN : 0040-8727
ISSN-L : 0040-8727
Synthesis of Artificial Group A and B Substances
Hajime MasamuneSen-itiroh HakomoriHaruo NumabeZiroh AkamaSigetosi Kamiyama
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1955 Volume 61 Issue 2-3 Pages 283-301

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Abstract
1. To verify our hypothesis regarding the configuration requisite for developing A and B group specificity, we have prepared a number of N-glycosides, of which the following proved typically group active: phos-phatidyl-(α-glutamyl)-ethanolamine-N-β-(N-acetyl)-glucosaminido-4-β-galactosido-2-β-(N-acetyl)-glucosaminido-4-β-galactoside (I), 2) hydro-phosphatidyl-(γ-carbomethoxy-α-aminobutyryl-glycyl-glycyl)-ethanolami-ne-N-β-(N-acetyl)-glucosaminido-4-β-galactosido-2-β-(N-acetyl)-gluco-saminido-4-β-galactoside (II), hydrophosphatidyl-(γ-carbomethoxy-α-ami-nobutyryl-glycyl-glycyl)-ethanolamine-N-β-(N-acetyl)-glucosaminido-4-β-galactoside (III), α-glutamyl-(α, α'-dipalmitylglycero-β-phosphoryl)-etha-nolamine-N-β-(N-acetyl)-glucosaminido--4-β-galactoside (IV), γ-glutamyl-(α, α'-dipalmitylglycero-β-phosphoryl)-ethanolamine-N-β-(N-acetyl)-gluco-saminido--4-β-galactoside (V), sphingosine-N-α-(N-acetyl)-glucosaminido-4-β-galactosido-2-β-(N-acetyl)-glucosaminido-4-β-galactoside (VI), sphin-gosine-N-α-(N-acetyl)-glucosaminido-4-β-galactoside (VII), α-sphingosine (Niemann)-N-α-(N-acetyl)-glucosaminido-4-β-galactoside (VIII), 1-O-pal-mitylsphingosine-N-α-(N-acetyl)-glucosaminido-4-β-galactoside (IX).
2. I-V were Group B active at dilutions of 1:3.2×103, 1:3.2×103, 1:1.6×103, 1:3.2×103 and 1:1.6×103 respectively and VI-IX Group A active at dilutions of 1:3.2×103, 1:1.6×103, 1:1.6×103 and 1:1.6×103 respectively.
3. Behaviours of VII and IV examined regarding the relationship between optical rotation and group potency showed that Group A syn-thetical substances are α-N-glycosides' and Group B substances β-N-glyco-sides, suggesting in turn that in natural Group A and B substances the carbohydrate moiety is bound to the non-carbohydrate moiety α- and β-glycosidically respectively in the molecule.
The expenses of this investigation were defrayed by a grant given from the Education Department through the Grant Committee for Scientific Researches, which is gratefully acknowledged.
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© Tohoku University Medical Press
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