Chiral Recognition and Separation of Amino Acids by Means of a Copper(II) Complex of Histamine Monofunctionalized .beta.-Cyclodextrin

Corradini, Roberto; Dossena, Arnaldo; Impellizzeri, Giuseppe; Maccarrone, Giuseppe; Marchelli, Rosangela; Rizzarelli, Enrico; Sartor, Giorgio; Vecchio, Graziella

doi:10.1021/ja00101a050

Cited by 100 publications

(68 citation statements)

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“…Good results have been obtained by Marchelli, Rizzarelli et al, 8 who pointed out the particular affinity of Cu(II)-6-deoxy-6-histamine-b-cyclodextrin for D-enantiomer of some native a-aminoacids. Only recently, Liu et al, 9 studying the binding properties of some organoselenomodified-b-cyclodextrins, reported that mono-2-phenylseleno-2-deoxy-b-cyclodextrin gives a high L-enantioselectivity for the inclusion complexation of leucine (up to 8.4).…”

Section: Introductionmentioning

confidence: 91%

Stability and stoichiometry of some binary fluorophore–cyclodextrin complexes

et al. 2004

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Abstract-The stability and stoichiometric ratio of binary complexes among five fluorophores and b-cyclodextrin (b-CD) or heptakis-(6-amino-6-deoxy)-b-cyclodextrin (am-b-CD) were determined by means of fluorescence measurements in borate buffer at pH¼8.0 and 9.0. Structure of both host and guest affected the characteristics of the binary complexes. Pyrene and anthraquinone formed a 1:2 (fluorophore: cyclodextrin) complex with both cyclodextrins. Xanthone formed 1:1 complex with b-CD and 1:2 complex with am-b-CD. A more defined behaviour was observed for crysene. In fact, both stoichiometric different complexes were detected with both hosts. Only 1:1 complexes were observed for antracene. The complex stability was affected by the pH of the solution. MM2 calculations were performed in order to gain information about the forces working on the formation of complexes. q

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Section: Introductionmentioning

confidence: 91%

Stability and stoichiometry of some binary fluorophore–cyclodextrin complexes

et al. 2004

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“…The 1 H and 13 C NMR spectra were obtained using a JEOL JNM-AL400 spectrometer at 400 MHz and 100 MHz respectively with tetramethylsilane as the internal reference. NMR measurements were performed at the Central Research Facilities of Chungnam National University.…”

Section: Methodsmentioning

confidence: 99%

“…[8][9][10][11][12][13][14][15][16][17][18] This form of host is referred to as a metalloreceptor. The construction of hosts with metal ions in the scaffold has allowed the binding of many structurally sophisticated guests.…”

mentioning

confidence: 99%

Convergent Synthesis of Macrocycles Composed of 5-Amino-2H-1,2,4-thiadiazolin-3-one or 5-Amino-2H-1,2,4-thiadiazoline-3-thione and 1,3-Benzenedimethanethiol

2004

Bulletin of the Korean Chemical Society

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“…26 In particular, we have shown that they are able to perform chiral recognition of aromatic amino acids. 27 This was the first chiral discrimination obtained by a combined inclusion/metal assisted coordination approach.…”

Section: Introductionmentioning

confidence: 97%

“…These studies showed that: 1) the presence of an aromatic group was essential for chiral discrimination; 2) the rigidity of the substituent could be important; 3) the preferred cis coordination of the amino group of the ligand and of the amino acid (''cis effect'') in the ternary complexes could be assumed. 26 In order to investigate the magnitude and nature of the interactions which allow chiral recognition in aqueous solution and to further investigate the cis effect, we synthesized a new 2-(methylamino)-pyridine functionalized ␤-cyclodextrin (CDampy, Fig. 1) which possesses an aromatic moiety bound through a very short chain (only one methylene group).…”

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confidence: 99%