110575-51-4Relevant articles and documents
Studies on Peptides. CXLIII. Evaluation of β-Menthylaspartate for Peptide Synthesis
Yajima, Haruaki,Futaki, Shiroh,Otaka, Akira,Yamashita, Takeyoshi,Funakoshi, Susumu,et. al.
, p. 4356 - 4361 (2007/10/02)
The β-l-menthyl ester of aspartic acid, Asp(OMen), was found to be stable to trifluoroacetic acid (TFA) in an ice-bath for 3 h, but to be cleaved by HF or 1 M trifluoromethanesulfonic acid-thioanisole in TFA in an ice-bath within 60 min.Asp(OMen) was employed for the synthesis of tetragastrin, for which the use of diphenylsulfide, as an additional scavenger, is recommended to accelerate the acidolytic cleavage of this protecting group.This protecting group is superior to other available protecting groups so far examined in terms of suppression of base-catalyzed succinimide formation.Keywords - β-menthylaspartate; base-catalyzed succinimide formation; acid-catalyzed succinimide formation; hydrogen fluoride deprotection; trifluoromethanesulfonic acid deprotection; cation scavenger; diphenylsulfide; tetragastrin