RETRACTED: Toward an Optimal Oligosaccharide Ligand for Rat Natural Killer Cell Activation Receptor NKR-P1

Krist, Pavel; Herkommerová-Rajnochová, Eva; Rauvolfová, Jana; Semeňuk, Tomáš; Vavrušková, Petra; Pavlíček, Jiří; Bezouška, Karel; Petruš, Ladislav; Křen, Vladimı́r

doi:10.1006/bbrc.2001.5537

Cited by 46 publications

(27 citation statements)

References 38 publications

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“…It follows from our previous studies (Krist et al 2001;Křen 2003) that aminosugars are strong ligands of these activation receptors, with the possible application in in vivo stimulation of natural killer cells, especially due to the presence of the thiourea linkage, which is stable in vivo. The binding assays were essentially performed as described previously (Krist et al 2001;Fialová et al 2005), with fluorescently or radioactively labeled protein receptors, rat NKR-P1 and human CD69. D-Mannose served as a negative (noninhibitory) control carbohydrate and GlcNAc as a positive control, providing IC 50 values of 1.7 × 10 −5 M (NKR-P1A) and 1.0 × 10 −3 M (CD69).…”

Section: Biological Activity Of Products 4-6mentioning

confidence: 99%

Synthesis of LacdiNAc-terminated glycoconjugates by mutant galactosyltransferase - A way to new glycodrugs and materials

Bojarová¹,

Křenek²,

Wetjen

et al. 2009

Glycobiology

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Human placental β1,4-galactosyltransferase-I (EC 2.4.1.38) transfers the galactosyl moiety from UDP-Gal to various GlcNAc or Glc acceptors in vivo. Here, we describe the construction of its Y284L mutant as a His 6 propeptidecatβ4GalT1 construct, in which the Gal-transferase activity was totally abolished in favor of its GalNAc-transferase activity. We used this mutant in the synthesis of three monoand bivalent LacdiNAc glycomimetics with good yields. These compounds proved to be powerful ligands of two activation receptors of natural killer cells, NKR-P1 and CD69. A synthetic bivalent tethered di-LacdiNAc is the best currently known precipitation agent for both of these receptors and has promising potential for the development of immunoactive glycodrugs.

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Section: Biological Activity Of Products 4-6mentioning

confidence: 99%

Synthesis of LacdiNAc-terminated glycoconjugates by mutant galactosyltransferase - A way to new glycodrugs and materials

Bojarová¹,

Křenek²,

Wetjen

et al. 2009

Glycobiology

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“…5 Furthermore, D-GalNAc has been recently recognised as one of the strongest agonist of the NKR-P1 rat Natural Killer cells receptor. 6 Owing to the biological relevance of D-GalNAc, several approaches to its synthesis in the free form and/or to the synthesis of its derivatives have been proposed, using different carbohydrate starting materials. The two most exploited synthetic channels to D-GalNAc and its derivatives are those based (a) on the C-4 epimerization of the largely and cheaply available 7 mimicking thus the biosynthetic pathway, and (b) on the amination at C-2 of D-galactose with formal retention of configuration.…”

Section: Introductionmentioning

confidence: 99%

Stereoselective entry into the d-GalNAc series starting from the d-Gal one: a new access to N-acetyl-d-galactosamine and derivatives thereof

Guazzelli

Catelani

D’Andrea

et al. 2009

Carbohydrate Research

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-A new stereoselective preparation of N-aceyl-D-galactosamine (1b) starting from the know pmethoxyphenyl 3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-β-D-galactopyranoside (10) is described using a simple strategy based on: (a) epimerization at C-2 of 10 via oxidation-reduction to give the talo derivative 11, (b) amination with configurational inversion at C-2 of 11 via a SN2 on its 2-imidazylate, (c) anomeric deprotection of the pmethoxyphenyl β-D-galactosamine glycoside 14, (d) complete deprotection. Applying the same protocol to 2,3:5,6:3',4'-tri-O-isopropylidene-6'-O-(1-methoxy-1-methylethyl)-lactose dimethyl acetal (4), directly obtained through acetonation of lactose, the disaccharide β-D-GalNAcp-(1→4)-D-Glcp (1a) was obtained with complete stereoselectivity in good (40%) overall yield from lactose.

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“…[2,3] The b-D-ManNAcp residue is a component of the natural spacer unit linking teichoic acids to the peptidoglycan chain in some Gram-positive bacteria. [4] More recently, Kren and co-workers [5] demonstrated that ManNAc is the strongest 2-acetamido-2-deoxyhexose ligand for the natural killer cell activating protein (NKR-P1). [5] Furthermore, disaccharides containing ManNAc unit at the reducing end were proved to have the highest affinity for the NKR-P1 receptors.…”

Section: Introductionmentioning

confidence: 99%

A New Preparation of the Disaccharide β‐D‐ManNAcp‐(1 → 4)‐D‐Glc from Lactose Through a Highly Stereoselective β‐D‐Galpto β‐D‐ManNAcpTransformation

Attolino¹,

Catelani²,

D’Andrea³

et al. 2004

Journal of Carbohydrate Chemistry

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RETRACTED: Toward an Optimal Oligosaccharide Ligand for Rat Natural Killer Cell Activation Receptor NKR-P1

Cited by 46 publications

References 38 publications

Synthesis of LacdiNAc-terminated glycoconjugates by mutant galactosyltransferase - A way to new glycodrugs and materials

Synthesis of LacdiNAc-terminated glycoconjugates by mutant galactosyltransferase - A way to new glycodrugs and materials

Stereoselective entry into the d-GalNAc series starting from the d-Gal one: a new access to N-acetyl-d-galactosamine and derivatives thereof

A New Preparation of the Disaccharide β‐D‐ManNAcp‐(1 → 4)‐D‐Glc from Lactose Through a Highly Stereoselective β‐D‐Galpto β‐D‐ManNAcpTransformation

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