Skip to main content
SpringerLink
Log in

Gangliosides Synthesis

  • Reference work entry
  • First Online:
Glycoscience: Biology and Medicine

Abstract

Various methodologies for the chemical synthesis of gangliosides have been explored so far and a lot of natural gangliosides including their structural analogues have been synthesized during the past three decades. Key technologies in the synthesis of gangliosides involve α-stereoselective sialylation and the introduction of the ceramide moiety into the oligosaccharide part. This chapter introduces two major strategies for ganglioside synthesis including the most commonly used one and the recently developed glucosylceramide cassette approach as well as natural gangliosides for which the total synthesis has been successfully achieved.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 899.99
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Hardcover Book
USD 549.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  • Ando H, Kiso M (2008) Selective α-sialylation. In: Fraser-Reid BO, Tatsuta K, Thiem J (eds) Glycoscience, vol 2, 2nd edn. Springer, Berlin/Heiderberg, pp 1313–1359

    Chapter  Google Scholar 

  • Ando H, Ishida H, Kiso M, Hasegawa A (1997) A synthetic approach to the c-series gangliosides containing sialyl-α-(2→8)sialyl-α-(2→8)sialic acid: synthesis of ganglioside GT4, α-(2→6)GT4 and GT3. Carbohydr Res 300:207–217 (for GT4 and GT3)

    Article  CAS  PubMed  Google Scholar 

  • Ando T, Ishida H, Kiso M (2003) First total synthesis of α-(2→3)/α-(2→6)-disialyl lactotetraosyl ceramide and disialyl Lewis A ganglioside as cancer-associated carbohydrate antigens. Carbohydr Res 338:503–514 (for Disialyl Lewis A)

    Article  CAS  PubMed  Google Scholar 

  • Fujikawa K, Nakashima S, Konishi M, Fuse T, Komura N, Ando T, Ando H, Yuki N, Ishida H, Kiso M (2011) The first total synthesis of ganglioside GalNAc-GD1a, a target molecule for autoantibodies in Guillain–Barré syndrome. Chem Eur J 17:5641–5651 (for GalNAc-GD1a)

    Article  CAS  PubMed  Google Scholar 

  • Hanashima S (2011) Recent strategies for stereoselective sialylation and their application to the synthesis of oligosaccharides. Trends Glycosci Glycotechnol 23:111–121

    Article  CAS  Google Scholar 

  • Hasegawa A, Nagahama T, Ohki H, Kiso M (1989) A facile total synthesis of ganglioside GM2. J Carbohydr Chem 11:699–714 (for GM2)

    Article  Google Scholar 

  • Hasegawa A, Nagahama T, Kiso M (1992) A facile, systematic synthesis of ganglio-series gangliosides: total synthesis of gangliosides GM1 and GD1a. Carbohydr Res 235:C13–C17 (for GM1 and GD1a)

    Article  CAS  PubMed  Google Scholar 

  • Hasegawa A, Ishida H-K, Nagahama T, Kiso M (1993a) Total synthesis of gangliosides GM1 and GD1a. J Carbohydr Chem 12:703–718 (for GM1 and GD1a)

    Article  CAS  Google Scholar 

  • Hasegawa A, Ishida H-K, Isogai Y, Ishida H, Kiso M (1993b) Total synthesis of ganglioside GD2. J Carbohydr Chem 12:1217–1222 (for GD2)

    Article  CAS  Google Scholar 

  • Higuchi R, Inagaki M, Yamada K, Miyamoto T (2007) Biologically active gangliosides from echinoderms. J Nat Med 61:367–370

    Article  CAS  Google Scholar 

  • Hotta K, Komba S, Ishida H, Kiso M, Hasegawa A (1994) Synthesis of α-series ganglioside GM1α. J Carbohydr Chem 13:665–677 (for GM1α)

    Article  CAS  Google Scholar 

  • Hotta K, Ishida H, Kiso M, Hasegawa A (1995a) First total synthesis of a cholinergic neuron-specific ganglioside GQ1bα. J Carbohydr Chem 14:491–506 (for GQ1bα)

    Article  CAS  Google Scholar 

  • Hotta K, Kawase T, Ishida H, Kiso M, Hasegawa A (1995b) A total synthesis of β-series ganglioside GQ1β. J Carbohydr Chem 14:961–975 (for GQ1β)

    Article  CAS  Google Scholar 

  • Imamura A, Ando H, Ishida H, Kiso M (2009) Ganglioside GQ1b: efficient total synthesis and the expansion to synthetic derivatives to elucidate its biological roles. J Org Chem 74:3009–3023 (for GQ1b)

    Article  CAS  PubMed  Google Scholar 

  • Ishida H-K, Ohta Y, Tsukada Y, Kiso M, Hasegawa A (1993) A synthetic approach to polysialogangliosides containing α-sialyl-(2→8)-sialic acid: total synthesis of ganglioside GD3. Carbohydr Res 246:75–88 (for GD3)

    Article  CAS  PubMed  Google Scholar 

  • Ishida H-K, Ishida H, Kiso M, Hasegawa A (1994a) Total synthesis of gangliosides GQ1b and the related polysialogangliosides. Tetrahedron: Asymmetry 5:2493–2512 (for GD1b, GT1b and GQ1b)

    Article  CAS  Google Scholar 

  • Ishida H-K, Ishida H, Kiso M, Hasegawa A (1994b) Total synthesis of gangliosides GQ1b. Carbohydr Res 260:C1–C6 (for GQ1b)

    Article  CAS  PubMed  Google Scholar 

  • Ishida H, Miyawaki R, Kiso M, Hasegawa A (1996a) First total synthesis of sialyl globopentaosyl ceramide (V3Neu5AcGb5Cer) and its positional isomer (V6Neu5AcGb5Cer). J Carbohydr Chem 15:163–182 (for SGG)

    Article  CAS  Google Scholar 

  • Ishida H, Miyawaki R, Kiso M, Hasegawa A (1996b) Systematic synthesis of α-sialyl-(2→3)- and -(2→6)-isoglobopentaosylceramides (V3Neu5AciGb5Cer and V6Neu5AciGb5Cer). Carbohydr Res 284:179–190 (for Sialy iGb5)

    Article  CAS  PubMed  Google Scholar 

  • Ishida H-K, Ando H, Ito H, Ishida H, Kiso M, Hasegawa A (1997) Total synthesis of gangliosides GD1c and GT1a. J Carbohydr Chem 16:413–428 (for GD1c and GT1a)

    Article  CAS  Google Scholar 

  • Ito Y, Numata M, Sugimoto M, Ogawa T (1989) Highly stereoselective synthesis of ganglioside GD3. J Am Chem Soc 111:8508–8510 (for GD3)

    Article  CAS  Google Scholar 

  • Ito H, Ishida H, Kiso M, Hasegawa A (1997) First total synthesis of ganglioside GT1aα. Carbohydr Res 304:187–189 (1998) 306:581–585, (for GT1aα)

    Article  CAS  PubMed  Google Scholar 

  • Ito H, Ishida H, Waki H, Ando S, Kiso M (1999) Total synthesis of a cholinergic neuron-specific ganglioside GT1aα: a high affinity ligand for myelin-associated glycoprotein (MAG). Glycoconj J 16:585–598 (for GT1aα)

    Article  CAS  PubMed  Google Scholar 

  • Kameyama A, Ishida H, Kiso M, Hasegawa A (1990) Stereoselective synthesis of sialyl-lactotetraosylceramide and sialylneolactotetraosylceramide. Carbohydr Res 200:269–285 (for Sialyl Lc4 and Sialyl nLc4)

    Article  CAS  PubMed  Google Scholar 

  • Kameyama A, Ishida H, Kiso M, Hasegawa A (1991a) Total synthesis of sialyl Lewis X. Carbohydr Res 209:c1–c4 (for Sialyl Lewis X)

    Article  CAS  PubMed  Google Scholar 

  • Kameyama A, Ishida H, Kiso M, Hasegawa A (1991b) Total synthesis of tumor-associated ganglioside, sialyl Lewis X. J Carbohydr Chem 10:549–560 (for Sialyl Lewis X)

    Article  CAS  Google Scholar 

  • Kameyama A, Ishida H, Kiso M, Hasegawa A (1994) Total synthesis of tumor-associated ganglioside, sialyl Lea. J Carbohydr Chem 13:641–654 (for Sialyl Lewis A)

    Article  CAS  Google Scholar 

  • Komba S, Galustian C, Ishida H, Feizi T, Kannagi R, Kiso M (1999) The first total synthesis of 6-sulfo-de-N-acetylsialyl LewisX ganglioside: a superior ligand for human L-selectin. Angew Chem Int Ed 38:1131–1133 (for 6-Sulfo de-N-acetyl-sLeX)

    Article  CAS  Google Scholar 

  • Konishi M, Imamura A, Fujikawa K, Ando H, Ishida H, Kiso M (2013) Extending the glucosyl ceramide cassette approach: application in the total synthesis of ganglioside GalNAc-GM1b. Molecules 18:15153–15181 (for GalNAc-GM1b)

    Article  CAS  PubMed  Google Scholar 

  • Lassaletta JM, Schmidt RR (1995) Versatile approach to the synthesis of globoside glycosphingolipids synthesis of sialyl-galactosyl-globoside. Tetrahedron Lett 36:4209–4212 (for SGG)

    Article  CAS  Google Scholar 

  • Matsuzaki Y, Nunomura S, Ito Y, Sugimoto M, Nakahara Y, Ogawa T (1993) Stereocontrolled synthesis of GD2. Carbohydr Res 242:C1–C6 (for GD2)

    Article  CAS  PubMed  Google Scholar 

  • Murase T, Kameyama A, Kartha KPR, Ishida H, Kiso M, Hasegawa A (1989a) A facile, regio and stereoselective synthesis of ganglioside GM4 and its position isomer. J Carbohydr Chem 8:265–283 (for GM4)

    Article  CAS  Google Scholar 

  • Murase T, Ishida H, Kiso M, Hasegawa A (1989b) A facile, regio- and stereo-selective synthesis of ganglioside GM3. Carbohydr Res 188:71–80 (for GM3)

    Article  CAS  PubMed  Google Scholar 

  • Nakashima S, Ando H, Imamura A, Yuki N, Ishida H, Kiso M (2011) A first total synthesis of a hybrid-type ganglioside associated with amyotrophic lateral sclerosis-like disorder. Chem Eur J 17:588–597 (for X1)

    Article  CAS  PubMed  Google Scholar 

  • Nakashima S, Ando H, Saito R, Tamai H, Ishida H, Kiso M (2012) Efficiently synthesizing lacto-ganglio-series gangliosides by using a glucosyl ceramide cassette approach: the total synthesis of ganglioside X2. Chem Asian J 7:1041–1051 (for X2)

    Article  CAS  PubMed  Google Scholar 

  • Numata M, Sugimoto M, Koike K, Ogawa T (1987) Total synthesis of sialosylcerebroside, GM4. Carbohydr Res 163:209–225 (for GM4)

    Article  CAS  PubMed  Google Scholar 

  • Prabhanjan H, Ishida H, Kiso M, Hasegawa A (1991a) A facile total synthesis of ganglioside GM1b and its positional analog. Carbohydr Res 211:c1–c5, 220:127–143, (for GM1b)

    Article  PubMed  Google Scholar 

  • Prabhanjan H, Kiso M, Hasegawa A (1991b) Total synthesis of a disialoganglioside GD1α. Carbohydr Res 222:c1–c4 (for GD1α)

    Article  CAS  PubMed  Google Scholar 

  • Prabhanjan H, Aoyama K, Kiso M, Hasegawa A (1992) Synthesis of disialoganglioside GD1α and its positional isomer. Carbohydr Res 233:87–99 (for GD1α)

    Article  CAS  PubMed  Google Scholar 

  • Sakamoto H, Nakamura S, Tsuda T, Hashimoto S (2000) Chemoselective glycosidation strategy based on glycosyl donors and acceptors carrying phosphorus-containing leaving groups: a convergent synthesis of ganglioside GM3. Tetrahedron Lett 41:7691–7695

    Article  CAS  Google Scholar 

  • Sugimoto M, Ogawa T (1985) Synthesis of a hematoside (GM3-ganglioside) and a stereoisomer. Glycoconj J 2:5–9 (for GM3)

    Article  CAS  Google Scholar 

  • Sugimoto M, Numata M, Koike K, Nakahara Y, Ogawa T (1986) Total synthesis of gangliosides GM1 and GM2. Carbohydr Res 156:c1–c5 (for GM1 and GM2)

    Article  CAS  PubMed  Google Scholar 

  • Sugimoto M, Fujikura K, Nunomura S, Horisaki T, Ito Y, Ogawa T (1990a) A stereocontrolled total synthesis of a ganglio-ganglioside GM1b, IV3NeuAcαGgOse4Cer. Tetrahedron Lett 31:385–388 (for GM1b)

    Article  CAS  Google Scholar 

  • Sugimoto M, Fujikura K, Nunomura S, Ito Y, Ogawa T (1990b) Total synthesis of an extended ganglio-ganglioside, IV4GalNAcβGM1b. Tetrahedron Lett 31:1435–1438 (for GalNAc-GM1b)

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Applied Bio-organic Chemistry, Faculty of Applied Biological Sciences, Gifu University, 1-1 Yanagido, Gifu-shi, 501-1193, Gifu, Japan

    Makoto Kiso, Hideharu Ishida, Hiromune Ando & Akihiro Imamura

  2. Institute for Integrated Cell-Material Sciences (WPI-iCeMS), Kyoto University, Yoshida Ushinomiya-cho, Yoshida Ushinomiya-cho, Sakyo-ku, Kyoto, Japan

    Makoto Kiso & Hiromune Ando

Authors
  1. Makoto Kiso
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Hideharu Ishida
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Hiromune Ando
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Akihiro Imamura
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Makoto Kiso .

Editor information

Editors and Affiliations

  1. Systems Glycobiology Research Group, RIKEN-Max Planck Joint Research Center for Systems Chemical Biology, Wako, Saitama, Japan

    Naoyuki Taniguchi

  2. Tokyo Metropolitan Institute of Gerontology, Tokyo Metropolitan Geriatric Hospital and Institute of Gerontology, Tokyo, Japan

    Tamao Endo

  3. Department of Biological Chemistry, Johns Hopkins University School of Medicine, Baltimore, Maryland, USA

    Gerald W. Hart

  4. Department of Biomolecular Systems, Max-Planck-Institute of Colloids and Interfaces, Potsdam, Germany

    Peter H. Seeberger

  5. Academica Sinica, NanKang, T´ai-pei, Taiwan

    Chi-Huey Wong

Rights and permissions

Reprints and permissions

Copyright information

© 2015 Springer Japan

About this entry

Cite this entry

Kiso, M., Ishida, H., Ando, H., Imamura, A. (2015). Gangliosides Synthesis. In: Taniguchi, N., Endo, T., Hart, G., Seeberger, P., Wong, CH. (eds) Glycoscience: Biology and Medicine. Springer, Tokyo. https://doi.org/10.1007/978-4-431-54841-6_31

Download citation

Publish with us

Policies and ethics

Search

Navigation