118534-76-2Relevant academic research and scientific papers
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.
Synthesis of β-1 and β-2-Adamantylaspartates and their Evaluation for Peptide Synthesis
Okada, Yoshio,Iguchi, Shin,Kawasaki, Koichi
, p. 1532 - 1534 (2007/10/02)
β-1 and β-2-Adamantylaspartates, H-Asp(O-1-Ada)-OH and H-Asp(O-2-Ada)-OH respectively, were synthesized and their properties examined, showing possible application in solid-phase peptide synthesis when used in combination with the fluoren-9-ylmethoxycarbonyl (Fmoc) group, as an Nα-protecting group; both these new protecting groups can suppress aspartimide formation as a side reaction under acidic and basic conditions.
