Separation of the enantiomers of substituted dihydrofurocoumarins by HPLC using macrocyclic glycopeptide chiral stationary phases

Analytical and Bioanalytical Chemistry

Volumn 377, Issue 4, 2003, Pages 639-654

  Xiao, Tom Ling ^a   Rozhkov, Roman V ^a   Larock, Richard C ^a   Armstrong, Daniel W ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

Chiral stationary phases; Dihydrofurocoumarin; Enantiomer separation; HPLC; Macrocyclic glycopeptide

Indexed keywords

CHROMATOGRAPHIC ANALYSIS; COMPLEXATION; ENZYMES; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGEN BONDS; HYDROPHOBICITY; PHASE SEPARATION; SUBSTITUTION REACTIONS;

CHIRAL STATIONARY PHASES; DIHYDROFUROCOUMARIN; ENANTIOMER SEPARATION; MACROCYCLIC GLYCOPEPTIDES;

NITROGEN COMPOUNDS;

DRUG DERIVATIVE; GLYCOPEPTIDE; PSORALEN DERIVATIVE; RISTOCETIN; RISTOCETIN A; TEICOPLANIN; TEICOPLANIN AGLYCONE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMPARATIVE STUDY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGEN BOND; HYDROPHOBICITY; METHODOLOGY; STEREOISOMERISM;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; GLYCOPEPTIDES; HYDROGEN BONDING; HYDROPHOBICITY; MOLECULAR STRUCTURE; PSORALENS; RISTOCETIN; STEREOISOMERISM; TEICOPLANIN;

EID: 0347468896     PISSN: 16182642     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00216-003-2110-z     Document Type: Article

References (62)

1. Pathak MA, Kramer DM, Fitzpatrick TB (1973) Sunlight and man. University of Tokyo Press
2. Regan JD, Parrish JA (1982) The science of photomedicine. Plenum Press, New York
3. Gasparro EP (1989) Psoralen DNA photobiology. CRC Press, Boca Raton, FL
4. Guilet D, Helesbeux JJ, Seraphin D, Sevenet T, Richomme P, Bruneton J (2001) J Nat Prod 64:563
5. Via LD, Gia O, Magno SM, Santana L, Teijeira M, Unarte E (1999) J Med Chem 42:4405
6. Jasinskas A, Jasinskiene N, Langmore JP (1998) Biochim Biophys Acta 1397:285
7. Kang SY, Lee KY, Sung SH, Park MJ, Kim, YC (2001) J Nat Prod 64:683
8. Pescitelli NBG, Xiao TL, Rozhkov RV, Larock RC, Armstrong DW (2003) Org Biomol Chem 1:186
9. Lee D, Bhat KPL, Fong HHS, Farnsworth NRR, Pezzuto JM, Kinghom AD (2001) J Nat Prod 64:1286
10. Beiber RC, Ivie GW, Obertli EH, Holt DL (1983) Food Chem Toxicol 21:163
11. Erdelmeier CAJ, Meier B, Sticher O (1985) J Chromatogr 346:456
12. Stermitz FR, Thomas RD (1973) J Chromatogr 77:431
13. Stanjek V, Miksch M, Boland W (1997) Tetrahedron 53:17699
14. Rozhkov R, Larock R (2003) Org Lett 5:797
15. Armstrong DW, Tang Y, Chen S, Zhou Y, Bagwill C, Chen J-R (1994) Anal Chem 66:1473
16. Armstrong DW, Rundlett K, Reid GL III (1994) Anal Chem 66:1690
17. Armstrong DW, Rundlett KL, Chen J-R (1994) Chirality 6:496
18. Armstrong DW, Zhou Y (1994) J Liq Chromatogr 17:1695
19. Xiao TL, Armstrong DW, Methods in biotechnology, chiral separations - methods and protocols, in press
20. Armstrong DW (1996) Chimia 50:273
21. Gasper MP, Berthod A, Nair UB, Armstrong DW (1996) Anal Chem 68:2501
22. A Berthod, Y Liu, C Bagwill, DW Armstrong (1996) J Chromatogr A 731:123
23. Armstrong DW (1996) 211th ACS National Meeting, New Orleans, LA, March 24-28, 1996, book of abstracts
24. Pawlowska M, Armstrong DW (1994) Chirality 6:270
25. Chen S, Liu Y, Armstrong DW, Borrell JI, Martinez-Teipel B, Matallana JL (1995) Biochim Biophys Acta 1263:2703
26. Armstrong DW, Liu Y, Ekborgott KH (1995) Chirality 7:474
27. Chen S, Liu Y, Armstrong DW, Borrell JI, Martinez-Teipel B, Matallana JL (1995) J Liq Chromatogr 18:1495
28. Ward TJ, Dann CI. Blaylock A (1995) J Chromatogr A 715:337
29. Nair UB, Chang SSC, Armstrong DW, Rawjee YY, Eggleston DS, McArdle JV (1996) Chirality 8:590
30. Berthod A, Nair UB, Bagwill C, Armstrong DW (1996) Talanta 43:1767
31. Strege MA, Huff BE, Risely DS (1996) LCGC 14:144
32. Ward TJ (1996) LCGC 14:886
33. Ekborg-Ott KH, Armstrong DW (1997) Chiral separations: application and technology, chap 9, p 201
34. Kleidemigg OP, Kappe CO (1997) Tetrahedron Asymmetry 8:2057
35. Sharp VS, Risley DS, McCarthy S, Huff BE, Strege MA (1997) J Liq Chromatogr 20:887
36. Torok G, Peter A, Toth G, Tourwe D, Van Den Nest W, Iterbeke K, Armstrong DW (1998) Proc 25th Eur Pept Symp, p 302
37. Peter A, Torok G, Toth G, Tourwe D, Mannekens E, Van Den Nest W, Sapi J, Armstrong DW (1998) Proc 25th Eur Pept Symp, p 300
38. Ekborg-Ott KH, Kullman JP, Wang X, Gahm K, He L, Armstrong DW (1998) Chirality 10:627
39. Peter A, Torok G, Toth G, Van den Nest W, Laus G, Tourwe D, Armstrong DW (1998) Chromatographia 48:53
40. Ekborg-Ott K, Liu Y, Armstrong DW (1998) Chirality 10:434
41. Armstrong DW, Lee JT, Chang LW, Tetrahedron (1998) Asymmetry 9:2043
42. Aboul-Enein HY, Serignese V (1999) Chromatographia 13:520
43. Aboul-Enein HY, Serignese V (1998) Chirality 10:358
44. Joyce KB, Jones AE, Scott RJ, Biddlecombe RA, Pleasance S (1998) Rapid Commun Mass Spectrom 12:1899
45. Fried KM, Koch P, Wainer IW (1998) Chirality 10:484
46. Lehotay J, Hrobonová K, Krupcík J, Cizmárik J (1998) Pharmazie 53:863
47. Schneiderheinze JM, Armstrong DW, Berthod A (1999) Chirality 11:330
48. Armstrong DW, He L, Yu T, Lee JT, Liu Y-s (1999) Tetrahedron Asymmetry 10:37
49. D'Acquarica I, Gasparrini F, Misiti D, Villani C, Carotti A, Cellamare S, Muck S (1999) J Chromatogr A 857:145
50. Ramos LM, Bakhtiar R, Majumdar T, Hayes M, Tse F (1999) Rapid Commun Mass Spectrom 13:2054
51. Tesarova E, Bosakova Z, Zuskova I (2000) J Chromatogr A 879:147
52. Karlsson C, Karlsson L, Armstrong DW, Owens PK (2000) Anal Chem 72:4394
53. Berthod A, Chen X, Kullman JP, Armstrong DW, Gasparrini F, D'Acquarica I, Villani C, Carotti A (2000) Anal Chem 72:1767
54. Peyrin E, Ravelet C, Nicolle E, Villet A, Grosset C, Ravel A, Alary J (2001) J Chromatogr A 923:37
55. Xiao TL, Zhang B, Lee JT, Hui F, Armstrong DW (2001) J Liq Chromatogr Related Technol 24:2673
56. Berthod A, Xiao TL, Liu Y, Jenks WS, Armstrong DW (2002) J Chromatogr A 955:53
57. Sadek PC (1996) The HPLC solvent guide. Wiley, New York
58. Seaver C, Przybytek J (1995) LCGC Int 8:190-195 (April 1995)
59. Burdick and Jackson solvent guide, 3rd edn. Burdick and Jackson, Muskegon, Michigan, USA, 1990
60. Schneider RL (1975) Physical properties of some organic solvents, Eastman Org Chem Bull, vol 47, no 1
61. Chang SC, Reid GL, Chen S, Chang CD, Armstrong DW (1993) Trends Anal Chem 12:144
62. Armstrong DW, Chen S, Chang C, Chang S (1992) J Liq Chromatogr Related Technol 15:545