Alternate Modulation of Biological Activity of Stress Molecule, b-D-glucopyranosyl-cholesterol, by Chemical Modification of Sugar Moiety. Hypotheses concerning biochemical meaning of the new glycosides

Iga, Dumitru Petru; Popescu, Dumitru; Gitman, Silvia

Dumitru Petru Iga, Dumitru Popescu, Silvia Gitman

Alternate Modulation of Biological Activity of Stress Molecule, b-D-glucopyranosyl-cholesterol, by Chemical Modification of Sugar Moiety. Hypotheses concerning biochemical meaning of the new glycosides

Abstract:

We have synthesized, beside the presently consecrated stress molecule, b-D-glucopyranosyl-cholesterol, b-D-arabinopyranosyl-, a-L-arabinofuranosyl- and b- and a-D-(3-O-methyl)glucopyranosyl-cholesterol. Two types of glycosylation agents were used: peracylated sugar bromide, with CdCO3 as promotor, and peracetylated sugar in the presence of BF3·OBu2 as promoting agent, respectively. A chemical test was used for synthesis monitoring: Zemplén saponification of reaction mixture had to produce an amphiphilic glycoside migrating in the region of cerebrosides, by TLC in a suitable solvent system. All intermediates and final products have been characterized by 1H and 13C NMR spectroscopy as well as by chemical and chromatographical methods. In the virtue of the recently discovered biochemical relationships of cholesterol and cerebrosides (or glycosterols and ceramide) new biochemical hypotheses have been advanced concerning the meaning of these new glycosides.

Keywords:
L-arabinopyranose; L-arabinofuranose; 3-O-methyl D-glucose; cholesterol; glycosterol; NMR spectra

Issue: 2019, Volume 70, Issue 11

Pages: 3987-3990

Publication date: 2019/12/15

https://doi.org/10.37358/RC.70.19.11.7688

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Citation Styles

Cite this article as:
IGA, D.P., POPESCU, D., GITMAN, S., Alternate Modulation of Biological Activity of Stress Molecule, b-D-glucopyranosyl-cholesterol, by Chemical Modification of Sugar Moiety. Hypotheses concerning biochemical meaning of the new glycosides, Rev. Chim., 70(11), 2019, 3987-3990.

Vancouver
Iga DP, Popescu D, Gitman S. Alternate Modulation of Biological Activity of Stress Molecule, b-D-glucopyranosyl-cholesterol, by Chemical Modification of Sugar Moiety. Hypotheses concerning biochemical meaning of the new glycosides. Rev. Chim.[internet]. 2019 Nov;70(11):3987-3990. Available from: https://doi.org/10.37358/RC.70.19.11.7688

APA 6th edition
Iga, D.P., Popescu, D. & Gitman, S. (2019). Alternate Modulation of Biological Activity of Stress Molecule, b-D-glucopyranosyl-cholesterol, by Chemical Modification of Sugar Moiety. Hypotheses concerning biochemical meaning of the new glycosides. Revista de Chimie, 70(11), 3987-3990. https://doi.org/10.37358/RC.70.19.11.7688

Harvard
Iga, D.P., Popescu, D., Gitman, S. (2019). 'Alternate Modulation of Biological Activity of Stress Molecule, b-D-glucopyranosyl-cholesterol, by Chemical Modification of Sugar Moiety. Hypotheses concerning biochemical meaning of the new glycosides', Revista de Chimie, 70(11), pp. 3987-3990. https://doi.org/10.37358/RC.70.19.11.7688

IEEE
D.P. Iga, D. Popescu, S. Gitman, "Alternate Modulation of Biological Activity of Stress Molecule, b-D-glucopyranosyl-cholesterol, by Chemical Modification of Sugar Moiety. Hypotheses concerning biochemical meaning of the new glycosides". Revista de Chimie, vol. 70, no. 11, pp. 3987-3990, 2019. [online]. https://doi.org/10.37358/RC.70.19.11.7688

Text
Dumitru Petru Iga, Dumitru Popescu, Silvia Gitman,
Alternate Modulation of Biological Activity of Stress Molecule, b-D-glucopyranosyl-cholesterol, by Chemical Modification of Sugar Moiety. Hypotheses concerning biochemical meaning of the new glycosides,
Revista de Chimie,
Volume 70, Issue 11,
2019,
Pages 3987-3990,
ISSN 2668-8212,
https://doi.org/10.37358/RC.70.19.11.7688.
(https://revistadechimie.ro/Articles.asp?ID=7688)
Keywords: L-arabinopyranose; L-arabinofuranose; 3-O-methyl D-glucose; cholesterol; glycosterol; NMR spectra

RIS
TY - JOUR
T1 - Alternate Modulation of Biological Activity of Stress Molecule, b-D-glucopyranosyl-cholesterol, by Chemical Modification of Sugar Moiety. Hypotheses concerning biochemical meaning of the new glycosides
A1 - Iga, Dumitru Petru
A2 - Popescu, Dumitru
A3 - Gitman, Silvia
JF - Revista de Chimie
JO - Rev. Chim.
PB - Revista de Chimie SRL
SN - 2668-8212
Y1 - 2019
VL - 70
IS - 11
SP - 3987
EP - 3990
UR - https://doi.org/10.37358/RC.70.19.11.7688
KW - L-arabinopyranose
KW - L-arabinofuranose
KW - 3-O-methyl D-glucose
KW - cholesterol
KW - glycosterol
KW - NMR spectra
ER -

BibTex
@article{RevCh2019P3987,
author = {Iga Dumitru Petru and Popescu Dumitru and Gitman Silvia},
title = {Alternate Modulation of Biological Activity of Stress Molecule, b-D-glucopyranosyl-cholesterol, by Chemical Modification of Sugar Moiety. Hypotheses concerning biochemical meaning of the new glycosides},
journal = {Revista de Chimie},
volume = {70},
number = {11},
pages = {3987-3990},
year = {2019},
issn = {2668-8212},
doi = {https://doi.org/10.37358/RC.70.19.11.7688},
url = {https://revistadechimie.ro/Articles.asp?ID=7688}
}

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