Issue 5, 2012
From the journal:

Organic & Biomolecular Chemistry

The total synthesis of a ganglioside Hp-s1 analogue possessing neuritogenic activity by chemoselective activation glycosylation†

Yow-Fu Tsai,*a   Cheng-Hua Shih,a   Yu-Ting Su,a   Chun-Hsu Yao,a   Jang-Feng Lian,a   Chun-Chen Liao,a   Ching-Wu Hsia,b   Hao-Ai Shuib  and  Rashmi Rania  

* Corresponding authors

a Department of Chemistry, Chung Yuan Christian University, Chung Li 32023, Taiwan
E-mail: tsaiyofu@cycu.edu.tw
Fax: +886-3-2653399
Tel: +886-3-2653307

b Graduate Institute of Life Sciences, National Defense Medical Center, Taipei, Taiwan

Abstract

The total synthesis of ganglioside 2, an analogue of the ganglioside Hp-s1 (1) which displays neuritogenic activity toward the rat pheochromocytoma cell line PC-12 cell in the presence of nerve growth factor (NGF) with an effect (34.0%) greater than that of the mammalian ganglioside GM 1 (25.4%), was accomplished by applying a chemoselective-activation glycosylation strategy. Moreover, we also demonstrate that the synthesized ganglioside 2 exhibited neuritogenic activity toward the human neuroblastoma cell line SH-SY5Y without the presence of NGF.

Graphical abstract: The total synthesis of a ganglioside Hp-s1 analogue possessing neuritogenic activity by chemoselective activation glycosylation

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Article information

DOI
https://doi.org/10.1039/C2OB06827C
Article type
Communication
Submitted
31 Oct 2011
Accepted
29 Nov 2011
First published
30 Nov 2011

Org. Biomol. Chem., 2012,10, 931-934

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The total synthesis of a ganglioside Hp-s1 analogue possessing neuritogenic activity by chemoselective activation glycosylation

Y. Tsai, C. Shih, Y. Su, C. Yao, J. Lian, C. Liao, C. Hsia, H. Shui and R. Rani, Org. Biomol. Chem., 2012, 10, 931 DOI: 10.1039/C2OB06827C

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