Glycophanes, cyclodextrin-cyclophane hybrid receptors for apolar binding in aqueous solutions. A stereoselective carbohydrate-carbohydrate interaction in water

Coteron, Jose M.; Vicent, Cristina; Bosso, C.; Penadés, Soledad

doi:10.1021/ja00075a023

Cited by 86 publications

(26 citation statements)

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“…These novel macrocycles with 34 to 40 ring atoms are novel representatives of [2+2]-glycophanes. Initially, smaller glycophanes made from trehalose in lower yields were reported by Penadé s et al [7,9,10]. In the present case the excellent operation of the Richman-Atkins approach allowed quite pleasing yields and very large components (Scheme 4).…”

Section: Resultssupporting

confidence: 51%

“…According to their studies carbohydrate precursors are suitable for construction of enzyme models [3][4][5]. Also Penades et al could employ disaccharide crown ethers as chiral catalysts [6][7][8], and later reported on the complexation capacity of water-soluble carbohydratebased macrocyles for neutral molecules [9][10]. The distinctive feature of these host molecules resides in the linkage of cyclophane and saccharide building units.…”

Section: Introductionmentioning

confidence: 99%

“…Yield 15.6 g (86%); colourless syrup; [a] 8. Bis[methyl-6-amino-2,3-di-O-benzyl-6-deoxy-4-yloxya-D-glucopyranoside]-m-xylene(10) …”

mentioning

confidence: 99%

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Synthesis of carbohydrate-based azamacrocycles by Richman–Atkins cyclisation

Rathjens

Thiem

2010

Comptes Rendus. Chimie

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Section: Resultssupporting

confidence: 51%

Section: Introductionmentioning

confidence: 99%

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Synthesis of carbohydrate-based azamacrocycles by Richman–Atkins cyclisation

Rathjens

Thiem

2010

Comptes Rendus. Chimie

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“…The process of CCI was originally studied based on adhesion or interaction of glycosyl vesicles, liposomes, or specific glycosyl cluster assembly ("cyclophane") [1,2,29,30]. The early findings were later supported by studies using NMR spectroscopy [30,31], surface plasmon resonance spectroscopy (SPR) [6,32,33], atomic force microscopy (AFM) [5,34,35], electrospray ionization mass spectrometry [36,37], and transmission electron microscopy [38] (for review see [39][40][41].…”

Section: Discussionmentioning

confidence: 99%

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

et al. 2006

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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 beta-galactosidase, having three or four GlcNAc termini exposed. These OS, conjugated to phosphatidylethanolamine (PE), showed clear interaction with (3)H-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 GalNAcalpha1-3Gb4 (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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“…For example, glycosphingolipids (GSLs) on cell surfaces laterally aggregate to form a GSL microdomain that is associated with a variety of signal transduction proteins. Face-to-face interaction between 2 GSL microdomains on neighbouring cells initiates the (10,11), liposomes (12,13), self-assembled monolayers (SAMs) on gold nano-particles (14)(15)(16)(17)(18)(19) and atomic force microscope (AFM) tips (19,20), and other systems (21). Matsuura et al reported speciˆc interactions between oligosaccharide-appended polymers and oligosaccharide-appended monolayers at air-water or water-solid interface (22)(23)(24)(25)(26).…”

Section: A Introductionmentioning

confidence: 99%

Intramolecular approach to investigating carbohydrate-carbohydrate interactions

Hasegawa¹

2009

TIGG

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Speciˆc carbohydrate-carbohydrate interactions on the cell surfaces are now widely believed to participate in various biological events, such as cell-cell adhesions and signal transductions. The author has used an intramolecular approach to investigate the carbohydrate-carbohydrate interactions by using small glycoclusters in which their conformational transitions are energetically coupled with intramolecular carbohydrate-carbohydrate interactions. For example, the intramolecular carbohydrate-carbohydrate interaction was monitored on the basis of the helixcoil transition of the glycosylated a-helical peptide. The rotational transition along molecular axes was also utilized in the m-oxo-bisporphyrinatoiron-based and ferrocenebased systems to monitor the carbohydrate-carbohydrate interactions. In all these systems, it was proven that speciˆc cations induce speciˆc interactions between the oligosaccharides.

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Glycophanes, cyclodextrin-cyclophane hybrid receptors for apolar binding in aqueous solutions. A stereoselective carbohydrate-carbohydrate interaction in water

Cited by 86 publications

References 0 publications

Synthesis of carbohydrate-based azamacrocycles by Richman–Atkins cyclisation

Synthesis of carbohydrate-based azamacrocycles by Richman–Atkins cyclisation

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

Intramolecular approach to investigating carbohydrate-carbohydrate interactions

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