A1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä
Direct High-Performance Liquid Chromatographic Separation of Peptide Enantiomers: Study on Chiral Recognition by Systematic Evaluation of the Influence of Structural Features of the Chiral Selectors on Enantioselectivity (2002)
Czerwenka, C., Lämmerhofer, M., Maier, N. M., Rissanen, K., & Lindner, W. (2002). Direct High-Performance Liquid Chromatographic Separation of Peptide Enantiomers: Study on Chiral Recognition by Systematic Evaluation of the Influence of Structural Features of the Chiral Selectors on Enantioselectivity. Analytical Chemistry, 74(21), 5658-5666. https://doi.org/10.1021/ac020372l
JYU-tekijät tai -toimittajat
Julkaisun tiedot
Julkaisun kaikki tekijät tai toimittajat: Czerwenka, Christoph; Lämmerhofer, Michael; Maier, Norbert M.; Rissanen, Kari; Lindner, Wolfgang
Lehti tai sarja: Analytical Chemistry
ISSN: 0003-2700
eISSN: 1520-6882
Julkaisuvuosi: 2002
Volyymi: 74
Lehden numero: 21
Artikkelin sivunumerot: 5658-5666
Kustantaja: American Chemical Society (ACS)
Julkaisumaa: Yhdysvallat (USA)
Julkaisun kieli: englanti
DOI: https://doi.org/10.1021/ac020372l
Julkaisun avoin saatavuus: Ei avoin
Julkaisukanavan avoin saatavuus:
Tiivistelmä
All-R/all-S enantiomers of oligoalanines (Alan, n = 1−10) with N-terminal protection group have been separated by HPLC on chiral stationary phases based on various cinchona alkaloid selectors. Structure−enantioselectivity relationships derived by extensive selector structure optimization provided insights into binding mechanisms and chiral recognition. Their interpretation was supported by X-ray crystal structures of amino acid and dipeptide, respectively, in complex with chiral selector. Optimized selectors have bulky elements representing steric barriers and deep binding pockets that afforded very high enantioselectivities; e.g., for the all-R and all-S enantiomers of N-(3,5-dinitrobenzoyl)alanylalanine, an α-value of 20.0 (corresponding to ΔΔG of −7.43 kJ/mol) was obtained with a chiral stationary phase based on 6‘-(neopentoxy)-9-O-tert-butylcarbamoylcinchonidine. Further, a chiral stationary phase based on 1,4-bis(9-O-quinidinyl)phthalazine was able to distinguish between the all-R and all-S enantiomers of hepta- to decaalanine peptides with enantioselectivity values between 1.8 and 1.9, corresponding to ΔΔG of −1.46 and −1.59 kJ/mol, respectively.
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