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Volumn 20, Issue 7, 2008, Pages 820-827

Guest-dependent conformation of 18-crown-6 tetracarboxylic acid: Relation to chiral separation of racemic amino acids

Author keywords

Amino acid; Chiral resolution; Crown ether; Crystal structure; Molecular conformation; X ray analysis

Indexed keywords

18 CROWN 6 TETRACARBOXYLIC ACID; AMINE; AMINO ACID DERIVATIVE; AMMONIA; CARBOXYLIC ACID DERIVATIVE; CATION; CROWN COMPOUND; GLYCINE; AMINO ACID; CROWN ETHER; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS;

EID: 45849087669     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20550     Document Type: Article
Times cited : (28)

References (34)
  • 1
    • 33947092798 scopus 로고
    • Host-guest complexation. 12. Total optical resolution of amine and amino ester by chromatography
    • Sousa LR, Sogah GDY, Hofmann DH, Cram DJ. Host-guest complexation. 12. Total optical resolution of amine and amino ester by chromatography. J Am Chem Soc 1978;100:4569-4576.
    • (1978) J Am Chem Soc , vol.100 , pp. 4569-4576
    • Sousa, L.R.1    Sogah, G.D.Y.2    Hofmann, D.H.3    Cram, D.J.4
  • 2
    • 0343456237 scopus 로고
    • Host-guest complexation. 14. Host covalently bound to polystyrene resin for chromatographic resolution of enantiomers of amino acid and ester salts
    • Sogah GDY, Cram DJ. Host-guest complexation. 14. Host covalently bound to polystyrene resin for chromatographic resolution of enantiomers of amino acid and ester salts. J Am Chem Soc 1979;101:3035-3042.
    • (1979) J Am Chem Soc , vol.101 , pp. 3035-3042
    • Sogah, G.D.Y.1    Cram, D.J.2
  • 3
    • 0023658988 scopus 로고
    • Chromatographic separation of racemic amino acids by using chiral crown ether-coated reversed-phase packings
    • Shinbo T, Yamaguchi T, Nishimura K, Sugiura M. Chromatographic separation of racemic amino acids by using chiral crown ether-coated reversed-phase packings. J Chromatogr 1987;405:145-153.
    • (1987) J Chromatogr , vol.405 , pp. 145-153
    • Shinbo, T.1    Yamaguchi, T.2    Nishimura, K.3    Sugiura, M.4
  • 5
    • 0032076469 scopus 로고    scopus 로고
    • Enantiomer separation of amino compounds by a novel chiral stationary phase derived from crown ether
    • Machida Y, Nishi H, Nakamura K, Nakai H, Sato T. Enantiomer separation of amino compounds by a novel chiral stationary phase derived from crown ether. J Chromatogr A 1998;805:85-92.
    • (1998) J Chromatogr A , vol.805 , pp. 85-92
    • Machida, Y.1    Nishi, H.2    Nakamura, K.3    Nakai, H.4    Sato, T.5
  • 6
    • 0032948964 scopus 로고    scopus 로고
    • Enantiomer separation of hydrophobic amino compounds by high-performance liquid chromatography using crown ether dynamically coated chiral stationary phase
    • Machida Y, Nishi H, Nakamura K. Enantiomer separation of hydrophobic amino compounds by high-performance liquid chromatography using crown ether dynamically coated chiral stationary phase. J Chromatogr A 1999;830:311-320.
    • (1999) J Chromatogr A , vol.830 , pp. 311-320
    • Machida, Y.1    Nishi, H.2    Nakamura, K.3
  • 7
    • 14844337475 scopus 로고    scopus 로고
    • Chiral stationary phase covalently bound with a chiral pseudo-18-crown-6 ether for enantiomer separation of amino compounds using a normal mobile phase
    • Hirose K, Yongzhu J, Nakamura T, Nishioka R, Ueshige T, Tobe Y. Chiral stationary phase covalently bound with a chiral pseudo-18-crown-6 ether for enantiomer separation of amino compounds using a normal mobile phase. Chirality 2005;17:142-148.
    • (2005) Chirality , vol.17 , pp. 142-148
    • Hirose, K.1    Yongzhu, J.2    Nakamura, T.3    Nishioka, R.4    Ueshige, T.5    Tobe, Y.6
  • 8
    • 0031832960 scopus 로고    scopus 로고
    • Nuclear magnetic resonance studies for the chiral recognition of the novel chiral stationary phase derived from 18-crown-6 tetracarboxylic acid
    • Machida Y, Nishi H, Nakamura K. Nuclear magnetic resonance studies for the chiral recognition of the novel chiral stationary phase derived from 18-crown-6 tetracarboxylic acid. J Chromatogr A 1998; 810:33-41.
    • (1998) J Chromatogr A , vol.810 , pp. 33-41
    • Machida, Y.1    Nishi, H.2    Nakamura, K.3
  • 9
    • 0032566487 scopus 로고    scopus 로고
    • liquid chromatographic resolution of racemic amino acids and their derivatives on a new chiral stationary phase based on crown ether
    • Hyun MH, Jin JS, Lee W. liquid chromatographic resolution of racemic amino acids and their derivatives on a new chiral stationary phase based on crown ether. J Chromatogr A 1998;822:155-161.
    • (1998) J Chromatogr A , vol.822 , pp. 155-161
    • Hyun, M.H.1    Jin, J.S.2    Lee, W.3
  • 10
    • 33746474126 scopus 로고    scopus 로고
    • High-performance liquid chromatographic enantioseparation of -amino acid stereoisomers on a (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid-based chiral stationary phase
    • Berkecz R, Sztojkov-Ivanov A, Ilisz I, Forro E, Fulop F, Hyun MH, Peter AJ. High-performance liquid chromatographic enantioseparation of -amino acid stereoisomers on a (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid-based chiral stationary phase. J Chromatogr A 2006;1125: 138-143.
    • (2006) J Chromatogr A , vol.1125 , pp. 138-143
    • Berkecz, R.1    Sztojkov-Ivanov, A.2    Ilisz, I.3    Forro, E.4    Fulop, F.5    Hyun, M.H.6    Peter, A.J.7
  • 11
    • 0028290014 scopus 로고
    • Potential and limitations of an optically active crown ether for chiral separation in capillary zone electrophoresis
    • Kuhn R, Wagner J, Walbroehl Y, Bereuter T. Potential and limitations of an optically active crown ether for chiral separation in capillary zone electrophoresis. Electrophoresis 1994;15:828-834.
    • (1994) Electrophoresis , vol.15 , pp. 828-834
    • Kuhn, R.1    Wagner, J.2    Walbroehl, Y.3    Bereuter, T.4
  • 12
    • 0028841985 scopus 로고
    • Evaluation of an optically active crown ether for the chiral separation of di- and tripeptides
    • Kuhn R, Riester D, Fleckenstein B, Weismuller K. Evaluation of an optically active crown ether for the chiral separation of di- and tripeptides. J Chromatogr A 1995;716:371-379.
    • (1995) J Chromatogr A , vol.716 , pp. 371-379
    • Kuhn, R.1    Riester, D.2    Fleckenstein, B.3    Weismuller, K.4
  • 13
    • 0032883014 scopus 로고    scopus 로고
    • Enantiomeric separation by capillary electrophoresis using a crown ether as chiral selector
    • Kuhn R. Enantiomeric separation by capillary electrophoresis using a crown ether as chiral selector. Electrophoresis 1999;20:2605-2613.
    • (1999) Electrophoresis , vol.20 , pp. 2605-2613
    • Kuhn, R.1
  • 14
    • 0034963249 scopus 로고    scopus 로고
    • 18-crown-6-Tetracarboxylic acid as a chiral additive for the simultaneous separation of o-, m-, and p-enantiomers of phenylalanine family by capillary electrophoresis
    • Chen Z, Uchiyama K, Hobo T. 18-crown-6-Tetracarboxylic acid as a chiral additive for the simultaneous separation of o-, m-, and p-enantiomers of phenylalanine family by capillary electrophoresis. Enantiomer 2001;6:19-25.
    • (2001) Enantiomer , vol.6 , pp. 19-25
    • Chen, Z.1    Uchiyama, K.2    Hobo, T.3
  • 15
    • 0034926558 scopus 로고    scopus 로고
    • Interaction between 18-crown-6- tetracarboxylic acid and positional substituents of enantiomers and simultaneous separation of positional enantiomers of methyl-DL-tryptophans by capillary electrophoresis
    • Chen Z, Uchiyama K, Hobo T. Interaction between 18-crown-6- tetracarboxylic acid and positional substituents of enantiomers and simultaneous separation of positional enantiomers of methyl-DL-tryptophans by capillary electrophoresis. Electrophoresis 2001;22:2136-2142.
    • (2001) Electrophoresis , vol.22 , pp. 2136-2142
    • Chen, Z.1    Uchiyama, K.2    Hobo, T.3
  • 16
    • 0034629087 scopus 로고    scopus 로고
    • Wenzel TJ, Thurston JE. (+)-(18-Crown-6)-2,3,11,12-tetracarboxylic acid and its Ytterbium(III) complex as chiral NMR discriminating agents. J Org Chem 2000;65:1243-1248.
    • Wenzel TJ, Thurston JE. (+)-(18-Crown-6)-2,3,11,12-tetracarboxylic acid and its Ytterbium(III) complex as chiral NMR discriminating agents. J Org Chem 2000;65:1243-1248.
  • 17
    • 0037437690 scopus 로고    scopus 로고
    • Nuclear magnetic resonance studies for the chiral recognition of (+)-(R)-18-crown-6-tetracarboxylic acid to amino compounds
    • Machida Y, Kagawa M, Nishi H. Nuclear magnetic resonance studies for the chiral recognition of (+)-(R)-18-crown-6-tetracarboxylic acid to amino compounds. J Pharm Biomed Anal 2003;30:1929-1942.
    • (2003) J Pharm Biomed Anal , vol.30 , pp. 1929-1942
    • Machida, Y.1    Kagawa, M.2    Nishi, H.3
  • 18
    • 33751555211 scopus 로고    scopus 로고
    • Lovely AE, Wenzel TJ. Chiral NMR discrimination of piperidines and piperazines using (18-crown-6)-2,3,11,12-tetracarboxylic acid. J Org Chem 2006;71:9178-9182.
    • Lovely AE, Wenzel TJ. Chiral NMR discrimination of piperidines and piperazines using (18-crown-6)-2,3,11,12-tetracarboxylic acid. J Org Chem 2006;71:9178-9182.
  • 19
    • 10644261516 scopus 로고    scopus 로고
    • Structural scaffold of 18-crown-6 tetracarboxylic acid for optical resolution of chiral amino acid: X-ray crystal analyses and energy calculations of complexes of D- and L- isomers of tyrosine, isoleucine, methionine and phenylglycin
    • Nagata H, Nishi H, Kamigauchi M, Ishida T. Structural scaffold of 18-crown-6 tetracarboxylic acid for optical resolution of chiral amino acid: X-ray crystal analyses and energy calculations of complexes of D- and L- isomers of tyrosine, isoleucine, methionine and phenylglycin. Org Biomol Chem 2004;2:3470-3475.
    • (2004) Org Biomol Chem , vol.2 , pp. 3470-3475
    • Nagata, H.1    Nishi, H.2    Kamigauchi, M.3    Ishida, T.4
  • 20
    • 33645539967 scopus 로고    scopus 로고
    • Structural scaffold of 18-Crown-6 tetracarboxylic acid for optical resolution of chiral amino acid: X-ray crystal analyses of complexes of D- and L-Isomers of serine and glutamic acid
    • Nagata H, Nishi H. Kamigauchi M, Ishida T. Structural scaffold of 18-Crown-6 tetracarboxylic acid for optical resolution of chiral amino acid: X-ray crystal analyses of complexes of D- and L-Isomers of serine and glutamic acid. Chem Pharm Bull 2006;54:452-457.
    • (2006) Chem Pharm Bull , vol.54 , pp. 452-457
    • Nagata, H.1    Nishi, H.2    Kamigauchi, M.3    Ishida, T.4
  • 24
    • 0000412029 scopus 로고
    • Program for the molecular orbital calculation
    • Stewart JJP. Program for the molecular orbital calculation. J Comput Chem 1989;10:209.
    • (1989) J Comput Chem , vol.10 , pp. 209
    • Stewart, J.J.P.1
  • 25
    • 0000406218 scopus 로고
    • + cation: Molecular structure of an oxonium-macrocycle polyefher complex
    • + cation: molecular structure of an oxonium-macrocycle polyefher complex. J Am Chem Soc 1982:104;454-4543.
    • (1982) J Am Chem Soc , vol.104 , pp. 454-4543
    • Behr, J.P.1    Dumas, P.2    Moras, D.3
  • 26
    • 0033015841 scopus 로고    scopus 로고
    • Crystallographic studies for the chiral recognition of the novel chiral stationary phase derived from (+)-(R)-18-crown-6 tetracarboxylic acid
    • Machida Y, Nishi H, Nakamura K. Crystallographic studies for the chiral recognition of the novel chiral stationary phase derived from (+)-(R)-18-crown-6 tetracarboxylic acid. Chirality 1999:11;173-178.
    • (1999) Chirality , vol.11 , pp. 173-178
    • Machida, Y.1    Nishi, H.2    Nakamura, K.3
  • 27
    • 0343341479 scopus 로고
    • Molecular structure of the ethylenediammonium complex of a tetracarboxy-macrocyclic receptor molecule
    • Daly JJ, Schonholzer J. Molecular structure of the ethylenediammonium complex of a tetracarboxy-macrocyclic receptor molecule. Helv Chim Acta 1981:64;1444-1451.
    • (1981) Helv Chim Acta , vol.64 , pp. 1444-1451
    • Daly, J.J.1    Schonholzer, J.2
  • 28
    • 0002989629 scopus 로고
    • The crystal structure of γ-glycine
    • Iitaka Y. The crystal structure of γ-glycine. Acta Crystallogr 1961:14; 1-10.
    • (1961) Acta Crystallogr , vol.14 , pp. 1-10
    • Iitaka, Y.1
  • 30
    • 0033580290 scopus 로고    scopus 로고
    • The nature of the hydrated excess proton in water
    • Marx D, Tuckerman ME, Hutter J, Parrinello M. The nature of the hydrated excess proton in water. Nature 1999;397:601-604.
    • (1999) Nature , vol.397 , pp. 601-604
    • Marx, D.1    Tuckerman, M.E.2    Hutter, J.3    Parrinello, M.4
  • 31
    • 0037455154 scopus 로고    scopus 로고
    • New insight into the transport mechanism of hydrated hydroxide ions in water
    • Ludwig R. New insight into the transport mechanism of hydrated hydroxide ions in water. Angew Chem Int Ed 2003;42:258-260.
    • (2003) Angew Chem Int Ed , vol.42 , pp. 258-260
    • Ludwig, R.1
  • 33
    • 0037182850 scopus 로고    scopus 로고
    • The nature and transport mechanism of hydrated hydroxide ions in aqueous solution
    • Tuckerman ME, Marx D, Parrinello M. The nature and transport mechanism of hydrated hydroxide ions in aqueous solution. Nature, 2002;417:925-929.
    • (2002) Nature , vol.417 , pp. 925-929
    • Tuckerman, M.E.1    Marx, D.2    Parrinello, M.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.