Facile Resolution Of N-tert-butoxycarbonyl Amino Acids: The Importance Of Enantiomeric Purity In Peptide Synthesis

Abstract

Twenty five pairs of N-tert-butoxycarbonyl (N-t-Boc) protected racemic amino acids were separated using a hydroxypropyl derivatized β-cyclodextrin bonded phase column in the reversed-phase mode. Most of the N-t-Boc-amino acids are base-line separated in 30 minutes or less. The retention behavior, the effect of structure on chiral recognition, and the effect of mobile phase composition are discussed. It was found there is a maximum resolution value when the mobile phase contains from 5% to 10% acetonitrile (or ~20% methanol) for many of the N-t-Boc-amino acids. Others were found to resolve better with acetonitrile concentrations between 90 - 97%. It was found that the higher the pH, the shorter the retention and the better the resolution. The optimum concentration of buffer solution was 1% triethylammonium acetate. N-t-Bocamino acids are used extensively in peptide synthesis. Relatively small enantiomeric impurities in these starting materials can translate into peptide products containing significant, often unacceptable impurities. The relationship between the enantiomeric purity of the starting material (N-t-Boc-amino acids), the number of synthetic steps and the stereochemical purity of the final product is discussed. © 1992, Taylor & Francis Group, LLC. All rights reserved.

Department(s)

Chemistry

International Standard Serial Number (ISSN)

0148-3919

Document Type

Article - Journal

Document Version

Citation

File Type

text

Language(s)

English

Rights

© 2023 Taylor and Francis Group; Taylor and Francis, All rights reserved.

Publication Date

01 Jul 1992

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