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Volumn 22, Issue 3, 2010, Pages 336-346

Carboxymethylated cyclodextrins and their complexes with Pr(III) and Yb(III) as water-soluble chiral NMR solvating agents for cationic compounds

Author keywords

1H NMR spectroscopy; Carboxymethylated cyclodextrins; Cyclodextrins; Enantiomeric discrimination; Enantiomeric purity; Lanthanide shift reagent

Indexed keywords

1 METHYL 3 PHENYL PIPERAZINE; 2 METHYLINDOLINE; 3 (3 CYCLOPENTYLOXY 4 METHOXYBENZYL) 6 ETHYLAMINO 8 ISOPROPYL 3H PURINE; ALPHA CYCLODEXTRIN DERIVATIVE; AMINO ACID; CARBOXYMETHYL BETA CYCLODEXTRIN; CHLORPHENIRAMINE MALEATE; DOXYLAMINE; GAMMA CYCLODEXTRIN DERIVATIVE; LANTHANIDE; PHENIRAMINE MALEATE; PRASEODYMIUM COMPLEX; PROPRANOLOL; UNCLASSIFIED DRUG; WATER; YTTERBIUM;

EID: 75849142250     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20748     Document Type: Article
Times cited : (22)

References (47)
  • 2
    • 0037287499 scopus 로고    scopus 로고
    • Chiral reagents for the determination of enantiomeric excess and absolute configuration using NMR spectroscopy
    • Wenzel TJ, Wilcox JD. Chiral reagents for the determination of enantiomeric excess and absolute configuration using NMR spectroscopy. Chirality 2003;15:256-270.
    • (2003) Chirality , vol.15 , pp. 256-270
    • Wenzel, T.J.1    Wilcox, J.D.2
  • 4
    • 12044259565 scopus 로고
    • Enantioselective and diastereoselective molecular recognition of neutral molecules
    • Webb TH, Wilcox CS. Enantioselective and diastereoselective molecular recognition of neutral molecules. Chem Soc Rev 1993;22:383-395.
    • (1993) Chem Soc Rev , vol.22 , pp. 383-395
    • Webb, T.H.1    Wilcox, C.S.2
  • 5
    • 0000237404 scopus 로고
    • NMR determination of enantiomeric purity
    • Parker D. NMR determination of enantiomeric purity. Chem Rev 1991;91:1441-1447.
    • (1991) Chem Rev , vol.91 , pp. 1441-1447
    • Parker, D.1
  • 6
    • 0000502289 scopus 로고
    • NMR chiral solvating agents
    • Eliel EL, Wilen SH, editors
    • Pirkle WH, Hoover DJ. NMR chiral solvating agents. In: Eliel EL, Wilen SH, editors. Top Stereochem 1982;1:263-331.
    • (1982) Top Stereochem , vol.1 , pp. 263-331
    • Pirkle, W.H.1    Hoover, D.J.2
  • 8
    • 0000022380 scopus 로고
    • Cyclodextrins as chiral nuclear magnetic resonance shift reagents
    • MacNicol DD, Rycroft DS. Cyclodextrins as chiral nuclear magnetic resonance shift reagents. Tetrahedron Lett 1977;25:2173-2176.
    • (1977) Tetrahedron Lett , vol.25 , pp. 2173-2176
    • MacNicol, D.D.1    Rycroft, D.S.2
  • 9
    • 84989603742 scopus 로고
    • Cyclodextrins as chiral complexing agents in water, and their application to optical purity measurements
    • Greatbanks D, Pickford R. Cyclodextrins as chiral complexing agents in water, and their application to optical purity measurements. Magn Reson Chem 1987;25:208-215.
    • (1987) Magn Reson Chem , vol.25 , pp. 208-215
    • Greatbanks, D.1    Pickford, R.2
  • 11
    • 0000128860 scopus 로고
    • Proton NMR study of conformation of formyl-L-phenylalanyl-6-deoxy-6-amino- cyclomaltoheptaose that has excellent ability of chiral recognition
    • Saka W, Yamamoto Y, Inoue Y, Chujo R, Takahashi K, Hattori K. Proton NMR study of conformation of formyl-L-phenylalanyl-6-deoxy-6-amino- cyclomaltoheptaose that has excellent ability of chiral recognition. Bull Chem Soc Jpn 1990;63:3175-3182.
    • (1990) Bull Chem Soc Jpn , vol.63 , pp. 3175-3182
    • Saka, W.1    Yamamoto, Y.2    Inoue, Y.3    Chujo, R.4    Takahashi, K.5    Hattori, K.6
  • 12
    • 0001487563 scopus 로고
    • 19F nuclear magnetic resonance study of the diastereoisomer inclusion complexes formed between fluorinated amino acid derivatives and α-cyclodextrin in aqueous solution
    • 19F nuclear magnetic resonance study of the diastereoisomer inclusion complexes formed between fluorinated amino acid derivatives and α-cyclodextrin in aqueous solution. J Chem Soc Faraday Trans 1991;87:2699-2703.
    • (1991) J Chem Soc Faraday Trans , vol.87 , pp. 2699-2703
    • Brown, S.E.1    Coates, J.H.2    Lincoln, S.F.3    Coghlan, D.R.4    Easton, C.J.5
  • 14
    • 0011896449 scopus 로고
    • Use of cyclodextrins and their derivatives for chiral analysis by high field nuclear magnetic resonance spectroscopy
    • Taylor A, Blackledge CA, Nicholson JK, Williams DAR, Wilson ID. Use of cyclodextrins and their derivatives for chiral analysis by high field nuclear magnetic resonance spectroscopy. Analyt Proc 1992;29:229-231.
    • (1992) Analyt Proc , vol.29 , pp. 229-231
    • Taylor, A.1    Blackledge, C.A.2    Nicholson, J.K.3    Williams, D.A.R.4    Wilson, I.D.5
  • 15
    • 37049086007 scopus 로고
    • NMR differentiation of enantiomeric (+)- and (-)-α-pinene via complexation with cyclodextrins in water
    • Botsi A, Yannakopoulou K, Hadjoudis E, Perly B. NMR differentiation of enantiomeric (+)- and (-)-α-pinene via complexation with cyclodextrins in water. J Chem Soc Chem Commun 1993:1085-1086.
    • (1993) J Chem Soc Chem Commun , pp. 1085-1086
    • Botsi, A.1    Yannakopoulou, K.2    Hadjoudis, E.3    Perly, B.4
  • 16
    • 0001424451 scopus 로고
    • Direct determination of the enantiomeric purity of chiral trisubstituted allenes by using permethylated cyclodextrin as a chiral solvating agent
    • Uccello-Barretta G, Balzano F, Caporusso AM, Salvadori P. Direct determination of the enantiomeric purity of chiral trisubstituted allenes by using permethylated cyclodextrin as a chiral solvating agent. J Org Chem 1994;59:836-839.
    • (1994) J Org Chem , vol.59 , pp. 836-839
    • Uccello-Barretta, G.1    Balzano, F.2    Caporusso, A.M.3    Salvadori, P.4
  • 17
    • 0028129338 scopus 로고
    • Lanthanide-cyclodextrin complexes as probes for elucidating optical purity by NMR spectroscopy
    • Wenzel TJ, Bogyo MS, Lebeau EL. Lanthanide-cyclodextrin complexes as probes for elucidating optical purity by NMR spectroscopy. J Am Chem Soc 1994;116:4858-4865.
    • (1994) J Am Chem Soc , vol.116 , pp. 4858-4865
    • Wenzel, T.J.1    Bogyo, M.S.2    Lebeau, E.L.3
  • 18
    • 0344503308 scopus 로고    scopus 로고
    • 1H NMR study of the inclusion complexes of chiral aromatic guests with β-cyclodextrin and its derivatives: Discrimination of aromatic protons and chiral recognition
    • 1H NMR study of the inclusion complexes of chiral aromatic guests with β-cyclodextrin and its derivatives: discrimination of aromatic protons and chiral recognition. Bull Korean Chem Soc 1996;17:1052-1056.
    • (1996) Bull Korean Chem Soc , vol.17 , pp. 1052-1056
    • Park, K.K.1    Park, J.M.2
  • 19
    • 0033098235 scopus 로고    scopus 로고
    • Chiral recognition of phenylacetic acid derivatives by aminated cyclodextrins
    • Kitae T, Takashima H, Kano K. Chiral recognition of phenylacetic acid derivatives by aminated cyclodextrins. J Incl Phenom Macrocycl Chem 1999;33:345-359.
    • (1999) J Incl Phenom Macrocycl Chem , vol.33 , pp. 345-359
    • Kitae, T.1    Takashima, H.2    Kano, K.3
  • 20
    • 0031575388 scopus 로고    scopus 로고
    • Effect of β-cyclodextrin acetylation on the resolution of phenethylamines with capillary electrophoresis and nuclear magnetic resonance spectroscopy
    • Branch SK, Holzgrabe U, Jefferies TM, Mallwitz H, Oxley FJR. Effect of β-cyclodextrin acetylation on the resolution of phenethylamines with capillary electrophoresis and nuclear magnetic resonance spectroscopy. J Chromatogr A 1997;758:277-292.
    • (1997) J Chromatogr A , vol.758 , pp. 277-292
    • Branch, S.K.1    Holzgrabe, U.2    Jefferies, T.M.3    Mallwitz, H.4    Oxley, F.J.R.5
  • 22
    • 0032883742 scopus 로고    scopus 로고
    • Chiral recognition of verapamil by cyclodextrins studied with capillary electrophoresis, NMR spectroscopy, and electrospray ionization mass spectrometry
    • Chankvetadze B, Burjanadze N, Pintore G, Strickmann D, Bergenthal D, Blaschke G. Chiral recognition of verapamil by cyclodextrins studied with capillary electrophoresis, NMR spectroscopy, and electrospray ionization mass spectrometry. Chirality 1999;11:635-644.
    • (1999) Chirality , vol.11 , pp. 635-644
    • Chankvetadze, B.1    Burjanadze, N.2    Pintore, G.3    Strickmann, D.4    Bergenthal, D.5    Blaschke, G.6
  • 23
    • 0038666259 scopus 로고    scopus 로고
    • Partially versus exhaustively carbamoylated cyclodextrins: NMR investigation on enantiodiscriminating capabilities in solution
    • Uccello-Barretta G, Ferri L, Balzano F, Salvadori P. Partially versus exhaustively carbamoylated cyclodextrins: NMR investigation on enantiodiscriminating capabilities in solution. Eur J Org Chem 2003;2003:1741-1748.
    • (2003) Eur J Org Chem 2003 , pp. 1741-1748
    • Uccello-Barretta, G.1    Ferri, L.2    Balzano, F.3    Salvadori, P.4
  • 24
    • 0035917975 scopus 로고    scopus 로고
    • Hellriegel C, Handel H, Wedig M, Steinhauer S, Sorgel F, Albert K, Holzgrabe U. Study on the chiral recognition of the enantiomers of ephidrine derivatives with neutral and sulfated heptakis(2,3-O-diacetyl)-β- cyclodextrins using capillary electrophoresis, UV, nuclear magnetic resonance spectroscopy and mass spectrometry. J Chromatogr A 2001;914:315-324.
    • Hellriegel C, Handel H, Wedig M, Steinhauer S, Sorgel F, Albert K, Holzgrabe U. Study on the chiral recognition of the enantiomers of ephidrine derivatives with neutral and sulfated heptakis(2,3-O-diacetyl)-β- cyclodextrins using capillary electrophoresis, UV, nuclear magnetic resonance spectroscopy and mass spectrometry. J Chromatogr A 2001;914:315-324.
  • 25
    • 0032489535 scopus 로고    scopus 로고
    • Comparative capillary electrophoresis and NMR studies of enantioseparation of dimethindene with cyclodextrins
    • Chankvetadze B, Schulte G, Bergenthal D, Blaschke ,G. Comparative capillary electrophoresis and NMR studies of enantioseparation of dimethindene with cyclodextrins. J Chromatogr A 1998;798:315-323.
    • (1998) J Chromatogr A , vol.798 , pp. 315-323
    • Chankvetadze, B.1    Schulte, G.2    Bergenthal, D.3    Blaschke, G.4
  • 26
    • 0034354880 scopus 로고    scopus 로고
    • Complexation of voriconazole stereoisomers with neutral and anionic derivatized cyclodextrins
    • Owens PK, Coleman MW, Berridge JC. Complexation of voriconazole stereoisomers with neutral and anionic derivatized cyclodextrins. J Incl Phenom Macrocycl Chem 2000;38:133-151.
    • (2000) J Incl Phenom Macrocycl Chem , vol.38 , pp. 133-151
    • Owens, P.K.1    Coleman, M.W.2    Berridge, J.C.3
  • 27
    • 0034335902 scopus 로고    scopus 로고
    • 2\plus by anionic cyclodextrins. Chem Lett 2000;6:698-699.
    • 2\plus by anionic cyclodextrins. Chem Lett 2000;6:698-699.
  • 29
    • 0034897924 scopus 로고    scopus 로고
    • Chiral recognition of dipeptide methyl esters by an anionic β-cyclodextrin
    • Kano K, Hasegawa H, Miyamura M. Chiral recognition of dipeptide methyl esters by an anionic β-cyclodextrin. Chirality 2001;13:474-482.
    • (2001) Chirality , vol.13 , pp. 474-482
    • Kano, K.1    Hasegawa, H.2    Miyamura, M.3
  • 31
    • 1642331562 scopus 로고    scopus 로고
    • Sulfated and carboxymethylated cyclodextrins and their lanthanide complexes as chiral NMR discriminating agents
    • Wenzel TJ, Amoono EP, Shariff SS, Aniagyei SE. Sulfated and carboxymethylated cyclodextrins and their lanthanide complexes as chiral NMR discriminating agents. Tetrahedron: Asymmetry 2003;14:3099-3104.
    • (2003) Tetrahedron: Asymmetry , vol.14 , pp. 3099-3104
    • Wenzel, T.J.1    Amoono, E.P.2    Shariff, S.S.3    Aniagyei, S.E.4
  • 33
    • 34447334595 scopus 로고    scopus 로고
    • Heptakis[2,3-di-O-methyl-6-O-(L-valine-tert-butylamide-Nα- carbonylmethyl)]-β-cyclodextrin: A new multifunctional cyclodextrin CSA for the NMR enantiodiscrimination of polar and apolar substrates
    • Uccello-Barretta G, Nazzi S, Balzano F, Levkin PA, Schurig V, Salvadori P. Heptakis[2,3-di-O-methyl-6-O-(L-valine-tert-butylamide-Nα- carbonylmethyl)]-β-cyclodextrin: a new multifunctional cyclodextrin CSA for the NMR enantiodiscrimination of polar and apolar substrates. Eur J Org Chem 2007;2007:3219-3226.
    • (2007) Eur J Org Chem 2007 , pp. 3219-3226
    • Uccello-Barretta, G.1    Nazzi, S.2    Balzano, F.3    Levkin, P.A.4    Schurig, V.5    Salvadori, P.6
  • 34
    • 49049098354 scopus 로고    scopus 로고
    • External vs internal interactions in the enantio-discrimination of fluorinated α-amino acid derivatives by heptakis[2,3-di-O-acetyl-6-O- (tert-butyldimethylsilyl)]-β-cyclodextrin, a powerful chiral solvating agent for NMR spectroscopy
    • Uccello-Barretta G, Balzano F, Pertici F, Jicsinszky L, Sicoli G, Schurig V. External vs internal interactions in the enantio-discrimination of fluorinated α-amino acid derivatives by heptakis[2,3-di-O-acetyl-6-O- (tert-butyldimethylsilyl)]-β-cyclodextrin, a powerful chiral solvating agent for NMR spectroscopy. Eur J Org Chem 2008;2008:1855-1863.
    • (2008) Eur J Org Chem 2008 , pp. 1855-1863
    • Uccello-Barretta, G.1    Balzano, F.2    Pertici, F.3    Jicsinszky, L.4    Sicoli, G.5    Schurig, V.6
  • 35
    • 49049101458 scopus 로고    scopus 로고
    • Carboxymethylated cyclodextrins and their paramagnetic lanthanide complexes as chiral NMR solvating agents
    • Provencher KA, Wenzel TJ. Carboxymethylated cyclodextrins and their paramagnetic lanthanide complexes as chiral NMR solvating agents. Tetrahedron: Asymmetry 2008;19:1797-1803.
    • (2008) Tetrahedron: Asymmetry , vol.19 , pp. 1797-1803
    • Provencher, K.A.1    Wenzel, T.J.2
  • 36
    • 0001511660 scopus 로고
    • Formation and stability of inorganic complexes in solution
    • Job P. Formation and stability of inorganic complexes in solution. Ann Chem 1928;9:113-203.
    • (1928) Ann Chem , vol.9 , pp. 113-203
    • Job, P.1
  • 37
    • 0001582550 scopus 로고
    • Investigation of the composition and formation constant of molecular complexes
    • Sahai R, Loper GL, Lin SH, Eyring H. Investigation of the composition and formation constant of molecular complexes. Proc Natl Acad Sci USA 1974;71:1499-1503.
    • (1974) Proc Natl Acad Sci USA , vol.71 , pp. 1499-1503
    • Sahai, R.1    Loper, G.L.2    Lin, S.H.3    Eyring, H.4
  • 38
    • 33751554133 scopus 로고
    • On the use of the method of continuous variations
    • Gil VMS, Oliveira NC. On the use of the method of continuous variations. J Chem Educ 1990;67:473-478.
    • (1990) J Chem Educ , vol.67 , pp. 473-478
    • Gil, V.M.S.1    Oliveira, N.C.2
  • 39
    • 0000835931 scopus 로고    scopus 로고
    • NMR studies of cyclodextrins and cyclodextrin complexes
    • Schneider H-J, Hacket F, Rudiger V, Ikeda H. NMR studies of cyclodextrins and cyclodextrin complexes. Chem Rev 1998;98:1755-1786.
    • (1998) Chem Rev , vol.98 , pp. 1755-1786
    • Schneider, H.-J.1    Hacket, F.2    Rudiger, V.3    Ikeda, H.4
  • 40
    • 0005678923 scopus 로고
    • Cycloheptaamylose inclusion complexes. Proton magnetic resonance study
    • Demarco PV, Thakkar AL. Cycloheptaamylose inclusion complexes. Proton magnetic resonance study. J Chem Soc Chem Commun 1970:2-4.
    • (1970) J Chem Soc Chem Commun , pp. 2-4
    • Demarco, P.V.1    Thakkar, A.L.2
  • 41
    • 33847088699 scopus 로고
    • Proton NMR study of the inclusion of aromatic molecules in α-cyclodextrin
    • Wood DJ, Hruska FE, Saenger W. Proton NMR study of the inclusion of aromatic molecules in α-cyclodextrin. J Am Chem Soc 1977;99:1735-1740.
    • (1977) J Am Chem Soc , vol.99 , pp. 1735-1740
    • Wood, D.J.1    Hruska, F.E.2    Saenger, W.3
  • 43
    • 0028433898 scopus 로고
    • Distribution of substituents in carboxymethyl esters of cyclomaltoheptaose
    • Reuben J, Rao CT, Pitha J. Distribution of substituents in carboxymethyl esters of cyclomaltoheptaose. J Carbohydr Res 1994;258:281-285.
    • (1994) J Carbohydr Res , vol.258 , pp. 281-285
    • Reuben, J.1    Rao, C.T.2    Pitha, J.3
  • 44
    • 0005865680 scopus 로고
    • Upfield' and downfield shifts in the nuclear magnetic resonance spectrum of a tris(dipivalomethanato) europium(III) complex
    • Mazzocchi PH, Tamburin HJ, Miller GR. Upfield' and downfield shifts in the nuclear magnetic resonance spectrum of a tris(dipivalomethanato) europium(III) complex. Tetrahedron Lett 1971;12:1819-1820.
    • (1971) Tetrahedron Lett , vol.12 , pp. 1819-1820
    • Mazzocchi, P.H.1    Tamburin, H.J.2    Miller, G.R.3
  • 45
    • 0040161013 scopus 로고
    • Lanthanideinduced shifts in proton nuclear magnetic resonance spectra. I. Europium-induced shifts to higher fields
    • Shapiro BL, Hlubucek JR, Sullivan GR, Johnson LF. Lanthanideinduced shifts in proton nuclear magnetic resonance spectra. I. Europium-induced shifts to higher fields. J Am Chem Soc 1971;93:3281-3283.
    • (1971) J Am Chem Soc , vol.93 , pp. 3281-3283
    • Shapiro, B.L.1    Hlubucek, J.R.2    Sullivan, G.R.3    Johnson, L.F.4
  • 46
    • 37049138100 scopus 로고
    • Meliacins (limonoids). Tris(dipivalomethanato) europium-induced upfield and downfield shifts in the nuclear magnetic resonance spectra of the meliacins
    • Ekong DEU, Okogun JI, Shok M. Meliacins (limonoids). Tris(dipivalomethanato) europium-induced upfield and downfield shifts in the nuclear magnetic resonance spectra of the meliacins. J Chem Soc Perkin Trans 1972;1:653-655.
    • (1972) J Chem Soc Perkin Trans , vol.1 , pp. 653-655
    • Ekong, D.E.U.1    Okogun, J.I.2    Shok, M.3
  • 47
    • 0013102365 scopus 로고
    • Paramagnetic shift reagents. The nature of the interactions
    • Sanders JKM, Hanson SW, Williams DH. Paramagnetic shift reagents. The nature of the interactions. J Am Chem Soc 1972;94:5325-5335.
    • (1972) J Am Chem Soc , vol.94 , pp. 5325-5335
    • Sanders, J.K.M.1    Hanson, S.W.2    Williams, D.H.3


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