Identification of chirality of phenylthiohydantoin-D-amino acid residue of[D-Ala(2)]-methionine enkephalin by capillary electrophoresis: Suppressionand control of racemization ratio in the Edman sequencing method

Citation
Y. Kurosu et al., Identification of chirality of phenylthiohydantoin-D-amino acid residue of[D-Ala(2)]-methionine enkephalin by capillary electrophoresis: Suppressionand control of racemization ratio in the Edman sequencing method, J LIQ CHR R, 21(20), 1998, pp. 3125-3137
Citations number
26
Categorie Soggetti
Chemistry & Analysis","Spectroscopy /Instrumentation/Analytical Sciences
Journal title
JOURNAL OF LIQUID CHROMATOGRAPHY & RELATED TECHNOLOGIES
ISSN journal
10826076 → ACNP
Volume
21
Issue
20
Year of publication
1998
Pages
3125 - 3137
Database
ISI
SICI code
1082-6076(1998)21:20<3125:IOCOPA>2.0.ZU;2-G
Abstract
This paper describes the suppression and control of the racemization ratio (D or L/D+L) of phenylthiohydantoin (PTH) amino acids in the Edman sequenci ng method. Most of the racemization occurs in the cyclization/cleavage step . Although optimization of partial racemization using a mixture of TFA and boron trifluoride (BF3)-ethyl ether complex, which is effective in suppress ing racemization in the cyclization/cleavage reaction. The partial racemiza tion in PTH derivatization is often useful for DL differentiation, because a minor L- or D-peak produced by racemization can be used as an internal st andard in CE. Using the partial racemization method with mixed acids as a c yclization/cleavage reagent, the sequence determination of [D-Ala(2)]-methi onine enkephalin, with DL differentiation, was achieved on a sequencer.