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Interaction of N-linked glycans, having multivalent GlcNAc termini, with GM3 ganglioside

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A Publisher's Erratum to this article was published on 19 January 2007

Abstract

GM3 ganglioside interacts specifically with complex-type N-linked glycans having multivalent GlcNAc termini, as shown for (1) and (2) below. (1) Oligosaccharides (OS) isolated from ConA-non-binding N-linked glycans of ovalbumin, whose structures were identified as penta-antennary complex-type with bisecting GlcNAc, having five or six GlcNAc termini (OS B1, B2), or bi-antennary complex-type having two GlcNAc termini (OS I). OS I is a structure not previously described. (2) Multi-antennary complex-type N-linked OS isolated from fetuin, treated by sialidase followed by β-galactosidase, having three or four GlcNAc termini exposed. These OS, conjugated to phosphatidylethanolamine (PE), showed clear interaction with 3H-labeled liposomes containing GM3, when various doses of OS-PE conjugate were adhered by drying to multi-well polystyrene plates. Interaction was clearly observed only with liposomes containing GM3, but not LacCer, Gb4, or GalNAcα1-3Gb4 (Forssman antigen). GM3 interaction with PE conjugate of OS B1 or B2 was stronger than that with PE conjugate of OS I. GM3 interacted clearly with PE conjugate of N-linked OS from desialylated and degalactosylated fetuin, but not native fetuin. No binding was observed to cellobiose-PE conjugate, or to OS-PE conjugate lacking GlcNAc terminus. Thus, GM3, but not other GSL liposomes, interacts with various N-linked OS having multiple GlcNAc termini, in general. These findings suggest that the concept of carbohydrate-to-carbohydrate interaction can be extended to interaction of specific types of N-linked glycans with specific GSLs. Natural occurrence of such interaction to define cell biological phenomena is under investigation.

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Abbreviations

CB:

cellobiose

CCI:

carbohydrate-to-carbohydrate interaction

C/M/W:

chloroform/methanol/water

ConA:

Concanavalin A

GlcNAc:

N-acetylglucosamine

Gb4:

globoside (GalNAcβ3Galα4Galβ4Glcβ1Cer)

Gg3:

GalNAcβ4Galβ4Glcβ1Cer

GM3:

NeuAcα3Galβ4Glcβ1Cer

GSL:

glycosphingolipid

OS:

oligosaccharides

PC:

1,2-dimyristoyl-sn-glycero-3-phosphocholine

PE:

phosphatidylethanolamine (1,2-dipalmitoyl-sn-glycero-3-phosphoethanolamine)

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Acknowledgments

This work was supported by NIH/ National Institute of General Medical Science (R01 GM070593) by NIH/ National Cancer Institute (R01 CA080054), to SH, by Core Research for Evolutionary Science and Technology, Japan Science and Technology Agency, and by a Grant-in-Aid for Scientific Research on Priority Areas (17046017) from the Ministry of Education, Culture, Sports, Science and Technology of Japan. The Esquire LC mass spectrometer was purchased with support by National Science Foundation under Grant No. 9807748. We thank Dr. Kimie Murayama (Pacific Northwest Research Institute) for advice on ESIMS analysis of OS-PE conjugates, and Dr. Stephen D. Anderson for preparation of the MS.

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Author notes

  1. Ken-ichi Nakayama

    Present address: Institute of General Industrial Research, Kagawa, Japan

  2. Natalia Utkina

    Present address: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia

  3. Helen Ying Wang

    Present address: Department of Environmental and Molecular Toxicology, North Carolina State University, Raleigh, NC, USA

Authors and Affiliations

  1. Division of Biomembrane Research, Pacific Northwest Research Institute, and Department of Pathobiology, University of Washington, Seattle, WA, USA

    Seon-Joo Yoon, Ken-ichi Nakayama, Natalia Utkina, Helen Ying Wang & Sen-itiroh Hakomori

  2. Department of Structural Biology and Biomolecular Engineering, Graduate School of Pharmaceutical Sciences, Nagoya City University, Nagoya, Japan

    Noriko Takahashi, Hirokazu Yagi & Koichi Kato

  3. Department of Chemistry, University of Washington, Seattle, WA, USA

    Martin Sadilek

  4. Pacific Northwest Research Institute, 720 Broadway, Seattle, WA, 98122-4302, USA

    Sen-itiroh Hakomori

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All solvent ratios are by volume.

An erratum to this article can be found at http://dx.doi.org/10.1007/s10719-006-9027-7

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Yoon, SJ., Nakayama, Ki., Takahashi, N. et al. Interaction of N-linked glycans, having multivalent GlcNAc termini, with GM3 ganglioside. Glycoconj J 23, 639–649 (2006). https://doi.org/10.1007/s10719-006-9001-4

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