Anion receptor molecules. Synthesis and some anion binding properties of macrocyclic guanidinium salts

Dietrich, B.; Fyles, Thomas M.; Lehn, Jean‐Maríe; Pease, Lila G.; Fyles, Deborah L.

doi:10.1039/c39780000934

Cited by 131 publications

(56 citation statements)

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“…Thus, macrocycle 3 complexes PO 4 3À in water with log K ass = 1.7 and in MeOH/H 2 O (9:1) with log K ass = 3.1. [41] A variety of cleft-type mono-and bisguanidinium receptors have been shown to efficiently complex oxoanions in polar solvents; in complex 4, which was formed in Me 2 SO, two guanidinium residues are proposed to coordinate in a tetrahedral fashion to HPO 4 2À .…”

Section: The C a Nn Structural Motifmentioning

confidence: 99%

Phosphate Recognition in Structural Biology

2006

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Drug-discovery research in the past decade has seen an increased selection of targets with phosphate recognition sites, such as protein kinases and phosphatases, in the past decade. This review attempts, with the help of database-mining tools, to give an overview of the most important principles in molecular recognition of phosphate groups by enzymes. A total of 3003 X-ray crystal structures from the RCSB Protein Data Bank with bound organophosphates has been analyzed individually, in particular for H-bonding interactions between proteins and ligands. The various known binding motifs for phosphate binding are reviewed, and similarities to phosphate complexation by synthetic receptors are highlighted. An analysis of the propensities of amino acids in various classes of phosphate-binding enzymes showed characteristic distributions of amino acids used for phosphate binding. This review demonstrates that structure-based lead development and optimization should carefully address the phosphate-binding-site environment and also proposes new alternatives for filling such sites.

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Section: The C a Nn Structural Motifmentioning

confidence: 99%

Phosphate Recognition in Structural Biology

2006

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“…Since these concepts have been described in detail in previous volumes of this series and in other reviews [1], only some representative examples will be briefly presented here. We will concentrate more specifically on the binding of oxoanions, such as carboxylates and phosphates, since these are the most important anionic functional groups present in organic molecules.…”

Section: Introductionmentioning

confidence: 99%

Molecular recognition of organic acids and anions — Receptor models for carboxylates, amino acids, and nucleotides

Seel

Galán

Mendoza

1995

Topics in Current Chemistry

103

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“…The solid was washed with acetone (500 ml), dried, and washed with H 2 O (500 ml). The obtained solid was recrystallized (MeOH/Et 2 O 1 : 2) to provide 2 (4.81 g, 79% .1 9,13 .1 15,19 ]octacosa-1(25),3,5, 7(28),9,11,13 (27), 15,17,19(26),21,23-dodecaene-4,6,10,12,16,18,22,24-octol (all-cis-stereoisomer; 18). NBS (11.1 g, 62.4 mmol) was added at 208 to a suspension of 17 (10.00 g, 13.9 mmol) in butanone (133 ml) and MeOH (57 ml), and the soln.…”

Section: Experimental Partmentioning

confidence: 99%

“…In the past, macrocyclic and cleft-type receptors containing ammonium or guanidinium groups have often been investigated for both carboxylate and phosphate binding in aqueous solution. Efficient macrocyclic nucleotide receptors include protonated azacrown ethers [12] and azacryptands [13], tetrazonia [8.1.8.1]paracyclophanes [14], and sapphyrins [15]. Non-macrocyclic receptors containing one or two guanidinium ions for phosphate and nucleotide binding have been reported [16] [17].…”

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confidence: 98%

Tetrakis(phenylamidinium)-Substituted Resorcin[4]arene Receptors for the Complexation of Dicarboxylates and Phosphates in Protic Solvents

Sebo¹,

Diederich²,

Gramlich

2000

HCA

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Three bowl‐type cavitand receptors (1 – 3), consisting of a resorcin[4]arene core with four convergent phenylamidinium groups, were prepared in gram quantities by efficient synthetic routes (Schemes 1 and 2) for the recognition of organic anions in CD3OD and D2O. The key steps in the syntheses are the Suzuki cross‐coupling reactions between the tetraiodo cavitands 12, 13, and 23, respectively, with the m‐cyanophenylboronic ester 14 and subsequent conversion of the nitrile to amidinium groups by the Garigipati reaction. Compounds 1 and 2 displayed limited solubility in protic solvents, and evidence for stoichiometric host‐guest association between 2 and AMP (28) could only be obtained by FAB‐MS analysis of a complex precipitated from MeOH (Fig. 2). In contrast, receptor 3 with four triethyleneglycol monomethyl ether side chains was readily soluble in the protic environments, and complexation of isophthalates and nucleotides 25 – 37 was extensively studied by 1H‐NMR titrations and Job's method of continuous variation. In CD3OD and pure D2O, isophthalates 25 and 26 formed stable 1 : 2 host‐guest complexes (Table 1 and Fig. 3), whereas upon addition of borate (pH 9.2) or Tris/HCl buffer (pH 8.3) to the D2O solution, the tendency for higher‐order complexation vanishes. Stable 1 : 1 complexes formed in the buffered solutions (Fig. 4) with 5‐methoxyisophthalate being selectively bound over the 5‐NO2 derivative. Complexation‐induced upfield shifts of specific isophthalate 1H‐NMR resonances (Fig. 5) suggest a preferred inclusion of the methoxyphenyl ring into the receptor cavity. Cavitand 3 forms stable 1 : 1 host‐guest complexes with nucleotides in Tris/HCl‐buffered D2O. Association constants increase strongly with increasing guest charge in the series cAMP

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Anion receptor molecules. Synthesis and some anion binding properties of macrocyclic guanidinium salts

Cited by 131 publications

References 0 publications

Phosphate Recognition in Structural Biology

Phosphate Recognition in Structural Biology

Molecular recognition of organic acids and anions — Receptor models for carboxylates, amino acids, and nucleotides

Tetrakis(phenylamidinium)-Substituted Resorcin[4]arene Receptors for the Complexation of Dicarboxylates and Phosphates in Protic Solvents

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