Structural analysis of the oligosaccharide-alditols released by reductive β-elimination from the jelly coat of Rana utricularia eggs

Morelle, Willy; Strecker, Gérard

doi:10.1042/bj3210879

Cited by 13 publications

(26 citation statements)

References 17 publications

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“…2, 12 of them have novel structures and can be considered as specific to the R. arvalis species. Therefore, these results confirm our previous observations that revealed clearly the highly species‐specificity of carbohydrate chains released from 12 different amphibian oviducal mucins [8–17].…”

Section: Resultssupporting

confidence: 89%

“…The NMR parameters (Table 2) of this unit are typical of the (α1–2) linkage to Gal [25]. On the basis of our previous work, we suspected that the hexuronic acid was a GlcA unit, sometimes found in other amphibian carbohydrate molecules[9,13,14]. After carboxymethylation, reduction with NaBD 4 , permethylation, methanolysis and acetylation, the GC/MS analysis showed the presence of 6,6′‐D 2 ‐(2,3,4,6)‐Me 4 ‐Glc, showing the existence of GlcA in nonreducing terminal position.…”

Section: Resultsmentioning

confidence: 99%

“…The galactosyl unit of the core is not substituted as shown by its chemical shifts at δ H‐1 = 4.465 p.p.m., δ H‐2 = 3.566 p.p.m., δ H‐3 = 3.672 p.p.m. and δ H‐4 = 3.902 p.p.m., which are characteristic of the Gal(β1,3)GalNAc‐ol sequence [9,25]. By comparison with the spectrum of 50‐14B (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…Previous studies have shown a species‐specific structural diversity in carbohydrate chains of amphibian egg jelly coats [8–19]. Consequently, these carbohydrate chains represent new phenotypic markers of amphibian species and from a biological point of view, can be involved in species‐specific interaction gametes or in the specific host–parasite interaction [20].…”

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confidence: 99%

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Acquisition of species‐specific O‐linked carbohydrate chains from oviducal mucins inRana arvalis

Coppin

Maës

Flahaut

et al. 1999

European Journal of Biochemistry

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The extracellular matrix surrounding amphibian eggs is composed of mucin-type glycoproteins, highly O-glycosylated and plays an important role in the fertilization process. Oligosaccharide-alditols were released from the oviducal mucins of the anuran Rana arvalis by alkali-borohydride treatment in reduced conditions. Neutral and acidic oligosaccharides were fractionated by ion-exchange chromatographies and purified by HPLC. Each compound was identified by matrix assisted laser desorption ionization-time of flight (MALDI-TOF) spectrometry, NMR spectroscopy, electrospray ionization-tandem mass spectroscopy (ESI-MS/MS) and permethylation analyses. This paper reports on the structures of 19 oligosaccharide-alditols, 12 of which have novel structures. These structures range in size from disaccharide to octasaccharide. Some of them are acidic, containing either a glucuronic acid or, more frequently, a sulfate group, located either at the 6 position of GlcNAc or the 3 or 4 positions of Gal. This latter sulfation is novel and has only been characterized in the species R. arvalis. This structural analysis led to the establishment of several novel carbohydrate structures, demonstrating the structural diversity and species-specificity of amphibian glycoconjugates.Keywords: sulfated-oligosaccharides; NMR; amphibian; oviducal mucin.The amphibian eggs are surrounded by oviducal jellies, which can be structurally and chemically distinct from between species [1]. The jelly coats are made up of several concentric layers composed of mucin-type glycoproteins, highly O-glycosylated. These glycoproteins have been shown to play important roles in fertilization [2,3]. Many functions have been assigned to the egg jelly components such as sperm binding, sperm capacitation, induction of the acrosome reaction, prevention of species cross-fertilization, the block of polyspermy (anurans) and provision of a protective ionic environment for the developing embryo [4±7].Previous studies have shown a species-specific structural diversity in carbohydrate chains of amphibian egg jelly coats [8±19]. Consequently, these carbohydrate chains represent new phenotypic markers of amphibian species and from a biological point of view, can be involved in species-specific interaction gametes or in the specific host±parasite interaction [20]. In the present study, we have isolated neutral and acidic carbohydrate chains from the oviducal mucins of Rana arvalis, and determined the structure of 19 of them. M A T E R I A L S A N D M E T H O D S Sampling of jelly coat mucusEggs from R. arvalis, collected in France and Russia, were obtained from natural spawns. The jelly coat material was lyophilized. Isolation of oligosaccharide-alditolsO-linked oligosaccharides were released from the crude material by alkaline degradation in reduced conditions (1 m NaBH 4 ) to obtain stable carbohydrate chains. Total material was submitted to a cationic exchange chromatography on Dowex 50 Â 2 (200±400 mesh, H + form) to remove residual peptides. Neutral oligosaccharide-alditols ...

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Section: Resultssupporting

confidence: 89%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 99%

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Acquisition of species‐specific O‐linked carbohydrate chains from oviducal mucins inRana arvalis

Coppin

Maës

Flahaut

et al. 1999

European Journal of Biochemistry

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“…Of particular interest are several proposals suggesting the role of sugar chains as sperm receptors, due to the action of glycosidases or glycosyltransferases. Previous structural studies have demonstrated a remarkable species specificity in carbohydrate chains attached to the proteic axis of the oviducal mucins [5–11]. Consequently, these carbohydrate chains represent new phenotypic markers of amphibia species, and from a biological point of view, could be involved in species‐specific gamete‐recognition or in specific host–parasite interaction [12].…”

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confidence: 99%

Diversity of O‐linked glycosylation patterns between species

Mourad

Morelle

Neveu³

et al. 2001

European Journal of Biochemistry

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Amphibia egg jelly coats are formed by components secreted along the oviduct. These secretion products overlay the oocytes as they pass along the different oviducal portions. Mucin type glycoproteins are the major constituents of the egg jelly coats. In this study, the O-linked carbohydrate chains of the jelly coats surrounding the eggs of Rana ridibunda were released by alkaline borohydride treatment. Fractionation of the mixture of O-linked oligosaccharidealditols was achieved by a combination of chromatographic techniques including gel-permeation chromatography, ion-exchange chromatography and high-performance liquid chromatography using an amino-bonded silica column. The primary structures of these O-glycans were determined by one-dimensional and two-dimensional 1 H-NMR spectroscopy and matrix-assisted laser-desorption-ionization-time-of flight mass spectrometry. 25 oligosaccharide structures, possessing a core consisting of Gal(b1±3)GalNAc-ol with or without branching through a GlcNAc residue linked (b1±6) to the GalNAc residue (core type 2 or core type 1, respectively) are described. The most representative antennae are:Gal(b1-3)GalNAc(a1-4)Gal(b1-4)Gal and GlcA(b1-3)Gal(b1-3)GalNAc. These results confirm the species-specific O-glycosylation of Amphibia oviducal mucins. The significance of this observation should be linked to a symbiotic role of carbohydrates involved in host±parasite interactions.Keywords: Amphibia; mucins; Rana ridibunda; NMR; carbohydrates.A characteristic feature of amphibia eggs is the presence of a water-insoluble gelatinous matrix, termed the jelly coat, surrounding the egg. Jelly coat layers are synthesized by specific regions of the oviduct and are sequentially deposited as the egg is transported toward the cloaca. Interest in these oviductally derived investments has centered on their obligatory participation in the early events of fertilization. The jelly coats are the first barrier for fertilizing sperm that must be passed through before reaching the egg plasma membrane. Thus, the jelly coats play a key role in the process of fertilization by facilitating adherence of the spermatozoa to the egg surface and by acting to block polyspermy [1±4].Mucin type glycoproteins have been shown to be the major components of this coat and implicated in important roles in fertilization. Of particular interest are several proposals suggesting the role of sugar chains as sperm receptors, due to the action of glycosidases or glycosyltransferases. Previous structural studies have demonstrated a remarkable species specificity in carbohydrate chains attached to the proteic axis of the oviducal mucins [5±11]. Consequently, these carbohydrate chains represent new phenotypic markers of amphibia species, and from a biological point of view, could be involved in species-specific gamete-recognition or in specific host±parasite interaction [12].Moreover, these structural analyses have led to the definition of several new glycosyltransferase activities reponsible for the structural species specificity. Acc...

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1H NMR Structural-Reporter-Group Concepts in Carbohydrate Analysis

Vliegenthart

Kamerling

2007

Comprehensive Glycoscience

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Structural analysis of the oligosaccharide-alditols released by reductive β-elimination from the jelly coat of Rana utricularia eggs

Cited by 13 publications

References 17 publications

Acquisition of species‐specific O‐linked carbohydrate chains from oviducal mucins inRana arvalis

Acquisition of species‐specific O‐linked carbohydrate chains from oviducal mucins inRana arvalis

Diversity of O‐linked glycosylation patterns between species

1H NMR Structural-Reporter-Group Concepts in Carbohydrate Analysis

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