Enantioselective high-performance liquid chromatographic separation of N-methyloxycarbonyl unsaturated amino acids on macrocyclic glycopeptide stationary phases

Journal of Chromatography A

Volumn 1108, Issue 1, 2006, Pages 26-30

  Boesten, J M M ^a   Berkheij, M ^b   Schoemaker, H E ^a,b   Hiemstra, H ^b   Duchateau, A L L ^a  

^a DSM Pharmaceutical Products   (Netherlands)

^b UNIVERSITY OF AMSTERDAM   (Netherlands)

Author keywords

Chiral stationary phases; Enantiomer separation; Enzymatic hydrolysis; LC; N MOC amino acids

Indexed keywords

ESTERS; HYDROLYSIS; LIQUID CHROMATOGRAPHY; PH; PROTEINS; STEREOCHEMISTRY;

CHIRAL STATIONARY PHASES; ENANTIOMER SEPARATION; ENZYMATIC HYDROLYSIS; N-MOC-Α-AMINO ACIDS;

AMINO ACIDS;

AMINO ACID DERIVATIVE; ESTER DERIVATIVE; GLYCOPEPTIDE; MACROCYCLIC COMPOUND;

ARTICLE; ENANTIOSELECTIVITY; ENZYME ACTIVITY; ENZYME SUBSTRATE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; OPTICAL RESOLUTION; PH; PRIORITY JOURNAL; REVERSED PHASE LIQUID CHROMATOGRAPHY; SEPARATION TECHNIQUE;

AMINO ACIDS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; GLYCOPEPTIDES; STEREOISOMERISM;

EID: 32044475124     PISSN: 00219673     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chroma.2005.12.088     Document Type: Article

References (29)

1. J. Kaiser, S.S. Kinderman, B.C.J. van Esseveldt, F.L. van Delft, H.E. Schoemaker, R.H. Blaauw, and F.P.J.T. Rutjes Org. Biomol. Chem. 3 2005 3435
2. S.S. Kinderman, R. de Gelder, J.H. van Maarseveen, H.E. Schoemaker, H. Hiemstra, and F.P.J.T. Rutjes J. Am. Chem. Soc. 126 2004 4100
3. B.E. Maryanoff, H.-C. Zhang, J.H. Cohen, I.J. Turchi, and C.A. Maryanoff Chem. Rev. 104 2004 1431
4. J. Royer, M. Bonin, and J. Micouin Chem. Rev. 104 2004 2311
5. W.N. Speckamp, and M.J. Moolenaar Tetrahedron 56 2000 3817
6. H. Hiemstra, and W.N. Speckamp M.B. Trost I. Fleming C.H. Heathcock Comprehensive Organic Synthesis vol. 2 1991 Pergamon Oxford 1047 1082
7. W.J.N. Meester, J.H. van Maarseveen, H.E. Schoemaker, H. Hiemstra, and F.P.J.T. Rutjes Eur. J. Org. Chem. 2003 2519
8. L.B. Wolf, T. Sonke, K.C.M.F. Tjen, B. Kaptein, Q.B. Broxterman, H.E. Schoemaker, and F.P.J.T. Rutjes Adv. Synth. Catal. 343 2001 662
9. N.A. Nabood, and R. Nosal Tetrahedron Lett. 35 1994 3669
10. M. Yato, K. Homma, and A. Ishida Heterocycles 49 1998 233
11. J. Hang, S.K. Tian, L. Tang, and L. Deng J. Am. Chem. Soc. 123 2001 12696
12. V. Piette, M. Lämmerhofer, K. Bischoff, and W. Lindner Chirality 9 1997 157
13. D.W. Armstrong, Y. Tang, S. Chen, Y. Zhou, C. Bagwill, and J.-R. Chen Anal. Chem. 66 1994 1473
14. D.W. Armstrong, Y. Liu, and K.H. Ekborg-Ott Chirality 7 1995 474
15. A. Berthod, U.B. Nair, C. Bagwill, and D.W. Armstrong Talanta 43 1996 1767
16. K.H. Ekborg-Ott, Y. Liu, and D.W. Armstrong Chirality 10 1998 434
17. E. Tesařová, Z. Bosáková, and V. Pacáková J. Chromatogr. A 838 1999 121
18. K.H. Ekborg-Ott, X. Wang, and D.W. Armstrong Microchem. J. 62 1999 26
19. Q. Sun, S.V. Olesik, and J. Chromatogr B: Biomed. Sci. Appl. 745 2000 159
20. E. Tesařová, Z. Bosáková, and I. Zusková J. Chromatogr. A 879 2000 147
21. A. Péter, E. Vékes, L. Gera, J.M. Stewart, and D.W. Armstrong Chromatogr. Suppl. 56 2002 S79 S89
22. A. Péter, E. Vékes, A. Arki, D. Tourwe, and W. Lindner J. Sep. Sci. 26 2003 1125
23. Y. Liu, A. Berthod, C.R. Mitchell, T.L. Xiao, B. Zhang, and D.W. Armstrong J. Chromatogr. A 978 2002 185
24. Y. Yamazaki, N. Morohashi, and K. Hosono J. Chromatogr. 542 1991 129
25. O. Azzolina, D. Vercesi, S. Collina, and V. Ghislandi Il Farmaco 50 1995 221
26. H.H. Lo, C.H. Kao, D.S. Lee, T.K. Yang, and W.H. Hsu Chirality 50 2003 699
27. H.J.W. Henderickx, A.L.L. Duchateau, and P.C. Raemakers-Franken J. Chromatogr. A 1020 2003 69
28. Chirobiotic Handbook, 5th ed., Advanced Separation Technologies, Inc., Whippany, NJ, USA, 2004.
29. a prediction module, version 3.5, Advanced Chemistry Development, Inc., Toronto Ont., Canada, 1998.