Structure of three Kdn‐containing oligosaccharide‐alditols released from oviducal secretions of <i>Ambystoma tigrinum</i>: characterization of the carbohydrate sequence Fuc (α1–5) [Fuc (α1–4)] Kdn (α2—3/6)

Maës, Emmanuel; Wieruszeski, Jean‐Michel; Plancke, Yves; Strecker, Gérard

doi:10.1016/0014-5793(94)01425-z

Cited by 17 publications

(9 citation statements)

References 10 publications

(12 reference statements)

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“…As previously observed [9][10][11][12], the presence of Kdn α-2-6-linked to GalNAc-ol, instead of NeuAc, is reflected by the absence of NAc signal at δ ≈ 2.03, whereas the H-3ax and H-3eq multiplets show upfield shifts of δ ≈ −0.04, as compared to the NeuAc analog. This structure might be elongated from C-3 branch to form either compound 31 or compound 38.…”

Section: Continuedsupporting

confidence: 64%

“…Kdn is now acknowledged to be an ubiquitous component of vertebrate glycoconjugates, owing to the remarkable contribution of Dr Yasuo Inoue in the field of Sialobiology [1,22,23]. It was later found as the sole sialic acid present in jelly coats of Pleurodeles and Ambystoma species [9][10][11][12]. In these cases, the Kdn unit formed a part of O-glycans based on type 1, 2 and 3 core structures.…”

Section: Discussionmentioning

confidence: 99%

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Structure elucidation of NeuAc, NeuGc and Kdn-containing O-glycans released from Triturus alpestris oviductal mucins

et al. 2006

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Eggs from Amphibia are surrounded by several layers of jelly that are needed for proper fertilization. Jelly coat is composed of highly glycosylated mucin-type glycoproteins containing up to 60% of carbohydrates, which display a remarkable species-specificity. This material obtained from Triturus alpestris was submitted to reductive beta-elimination and the released oligosaccharide-alditols were further fractionated by HPLC. Structural characterization was performed through a combination of two dimensional (1)H-(1)H and (1)H-(13)C NMR and ESI-MS/MS analysis. Numerous carbohydrate chains are characterized by the presence of the Cad (Sd(a)) determinant, including respectively NeuAc, NeuGc or Kdn as a sialic acid. But the most significant O-glycan sequences which mark the difference between the jelly of T. alpestris and other studies amphibian jellies are polymers of GalNAc(beta 1-4)GlcNAc (LacdiNAc) which form part of the following sequence: HSO(3)(4)(GalNAcbeta 1-4GlcNAcbeta 1-3)(1-3)GalNAcbeta 1-4(GlcNAcbeta 1-3)(0-1)GlcNAcbeta 1-6GalNAc-ol.

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Section: Continuedsupporting

confidence: 64%

Section: Discussionmentioning

confidence: 99%

Structure elucidation of NeuAc, NeuGc and Kdn-containing O-glycans released from Triturus alpestris oviductal mucins

et al. 2006

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“…In oligosaccharide chains isolated from Mexican axolotl, and Xenopus laevis, KDN occurred as an internal residue to which a single Fuc or Fucα1 → 3Fuc unit was linked α1 → 4. In the egg jelly coat of other axolotl species (Ambystoma tigrinum, Ambystoma maculatum) KDN also occurred as internal residues monofucosylated at C4 or difucosylated at C4, and C5 [16][17][18]. Structures containing internal sialic acid substituted by sugar other than sialic acid are unusual for animal oligosaccharide units.…”

Section: Amphibian Egg Jelly Coatsmentioning

confidence: 94%

KDN (Deaminated neuraminic acid): Dreamful past and exciting future of the newest member of the sialic acid family

2006

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KDN is an abbreviation for 2-keto-3-deoxy-D-glycero-D-galacto-nononic acid, and its natural occurrence was revealed in 1986 by a research group including the present authors. Since sialic acid was used as a synonym for N-acylneuraminic acid at that time, there was an argument if this deaminated neuraminic acid belongs to the family of sialic acids. In this review, we describe the 20 years history of studies on KDN (KDNology), through which KDN has established its position as a distinct member of the sialic acid family. These studies have clarified that: (1) KDN occurs widely among vertebrates and bacteria similar to the occurrence of the more common sialic acid, N-acetylneuraminic acid (Neu5Ac), but its abundant occurrence in animals is limited to lower vertebrates. (2) KDN is found in almost all types of glycoconjugates, including glycolipids, glycoproteins and capsular polysaccharides. (3) KDN residues are linked to almost all glycan structures in place of Neu5Ac. All linkage types known for Neu5Ac; alpha2,3-, alpha2,4-, alpha2,6-, and alpha2,8- are also found for KDN. (4) KDN is biosynthesized de novo using mannose as a precursor sugar, which is activated to CMP-KDN and transferred to acceptor sugar residues. These reactions are catalyzed by enzymes, some of which preferably recognize KDN, but many others prefer Neu5Ac to KDN. In addition to these basic findings, elevated expression of KDN was found in fetal human red blood cells compared with adult red blood cells, and ovarian tumor tissues compared with normal controls. KDNase, an enzyme which specifically cleaves KDN-linkages, was discovered in a bacterium and monoclonal antibodies that specifically recognize KDN residues in KDNalpha2,3-Gal- and KDNalpha2,8-KDN-linkages have been developed. These have been used for identification of KDN-containing molecules. Based on past basic studies and variety of findings, future perspective of KDNology is presented.

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“…Le y in Pleurodeles waltl mucin [6,7]) prompted us to investigate new amphibian species. These first analyses, which were performed on urodeles and anouran species, led to the observation of a species-specific structural diversity which should be used as a basis for taxonomy [8][9][10][11][12][13][14][15][16]. The present paper describes the O-linked carbohydrate chains of the mucin collected from Rana utricularia egg jelly coats.…”

Section: Introductionmentioning

confidence: 93%

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

Morelle

Strecker²

1997

Biochemical Journal

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The O-linked oligosaccharides of the jelly coat surrounding the eggs of Rana utricularia were analysed by 1H-NMR spectroscopy. Comparison of their structures with those characterized from seven other amphibians confirms that the carbohydrate chains of the jelly coat mucins are markers of the species. The new sequence GlcNAc(beta1-3)GlcNAc(beta1-6)[Gal(beta1-3)]GalNAc-ol is characteristic of Rana utricularia. The presence of blood group A determinants constitutes the main feature of this mucin.

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Structure of three Kdn‐containing oligosaccharide‐alditols released from oviducal secretions of Ambystoma tigrinum: characterization of the carbohydrate sequence Fuc (α1–5) [Fuc (α1–4)] Kdn (α2—3/6)

Cited by 17 publications

References 10 publications

Structure elucidation of NeuAc, NeuGc and Kdn-containing O-glycans released from Triturus alpestris oviductal mucins

Structure elucidation of NeuAc, NeuGc and Kdn-containing O-glycans released from Triturus alpestris oviductal mucins

KDN (Deaminated neuraminic acid): Dreamful past and exciting future of the newest member of the sialic acid family

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

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