118534-81-9Relevant academic research and scientific papers
Aspartic acid derivatives
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, (2008/06/13)
New compounds N-α-9-fluorenylmethoxycarbonyl-aspartic acid-β-1-adamantyl esters are stable under the basic condition of the normal peptide condensation process and do not form succinimide. Peptides containing aspartic acid can be synthesized with high purity and at high yields by using N-α-9-fluorenylmethoxycarbonyl-aspartic acid-β-1-adamantyl ester.
Amino Acids and Peptides. Part 19. Synthesis of β-1-and β-2-Adamantyl Aspartates and their Evaluation for Peptide Synthesis
Okada, Yoshio,Iguchi, Shin
, p. 2129 - 2136 (2007/10/02)
β-1-and β-2-Adamantyl aspartates have been synthesized and their properties examined.Altough the 1-Ada group is labile to TFA, the 2-Ada group is unaffected during TFA treatment, but easily removable by methanesulphonic acid (MSA) at room temperature within 5 min.Both groups are unaffected by treatment with 55percent piperidine under conditions which easily cleave the fluoren-9-ylmethoxycarbonyl (Fmoc) group from α-amino group.Both groups can suppress aspartimide formation as a side reaction under acidic and basic conditions during the synthesis of aspartyl peptides. β-1-or β-2-Adamantyl aspartates may be applicable to solid-phase peptide synthesis in combination with Fmoc or Boc as an Nα-protecting group, respectively.Some properties of the aspartimide moiety are described.
