Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
The γ-Phenacyl and γ-p-Nitrobenzyl Esters to Minimize Side Reactions during Treatment of Glutamyl Peptides with Hydrogen Fluoride-Anisole Mixture
KENJI SUZUKINOBUYOSHI ENDOYUSUKE SASAKI
Author information
Keywords: zinc in 90% AcOH
JOURNAL FREE ACCESS

1977 Volume 25 Issue 10 Pages 2613-2616

Details
Abstract
For the synthesis of peptide containing glutamic acid residue (s) by solid phase peptide synthesis, γ-phenacyl or γ-nitrobenzyl ester group, which is stable to anhydrous hydrogen fluoride (HF), was used as γ-carboxyl protecting group of glutamic acid to minimize the side reactions. The protected peptide resins were treated with HF-anisole mixture followed by deprotection of the γ-carboxyl protecting group under mild conditions. This strategy gave a satisfactory result without detectable side reactions in the preparations of two model dipeptides, H-Ala-Glu-OH and H-Asn-Glu-OH, by solid phase peptide synthesis.
Content from these authors
© The Pharmaceutical Society of Japan
Previous article Next article
feedback
Top