Efficient acylation of the N-terminus of highly hindered C(alpha)(alpha)-disubstituted amino acids via amino acid symmetrical anhydrides.
[reaction: see text] Fmoc amino acid symmetrical anhydrides are efficient and readily available reagents for acylation of the N-terminus of highly hindered C(alpha)(alpha)-dialkylated alpha-amino acids. Comparison of a variety of coupling protocols showed that the symmetrical anhydride method always provided the superior results. This method was successfully applied to the solid-phase synthesis of a peptide containing three alpha(alpha)AAs at alternating positions.
Fu
Yanwen
Y
Department of Chemistry, Louisiana State University, Baton Rouge, Louisiana 70803, USA.
Hammer
Robert P
RP
D000215:Acylation; D000596:Amino Acids / Q000737:chemistry*; D000812:Anhydrides / Q000737:chemistry*; D006860:Hydrogen Bonding; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D017433:Protein Structure, Secondary; D012997:Solvents
D000596:Amino Acids; D000812:Anhydrides; D009842:Oligopeptides; D012997:Solvents