HBTU activation for automated Fmoc solid-phase peptide synthesis.
Excellent results have been obtained for the Fmoc solid-phase syntheses of peptides using the activating reagent 2-(1H-benzotriazol-1-yl)-1,1,3,3,-tetramethyluronium hexafluorophosphate (HBTU). Activation occurs very rapidly in N,N-dimethylformamide and N-methyl-pyrrolidone, optimal solvents for peptide-resin solvation. It has been observed that complete coupling reactions occur in only 10-30 min. Residues such as Arg, Ile, Leu and Val, which often require double coupling by other activation methods, react with high efficiency by single coupling when HBTU is used. The Fmoc/HBTU chemistry has recently been applied to the peptide synthesizers. The incorporation of trityl side-chain protection for Fmoc-Asn and Fmoc-Gln further enhances coupling efficiencies in difficult sequences.
Fields
C G
CG
Applied Biosystems Inc., Foster City, CA 94404.
Lloyd
D H
DH
Macdonald
R L
RL
Otteson
K M
KM
Noble
R L
RL
D000595:Amino Acid Sequence; D000596:Amino Acids / Q000032:analysis; D001331:Automation; D005449:Fluorenes; D007700:Kinetics; D008969:Molecular Sequence Data; D010455:Peptides / Q000138:chemical synthesis*; D010880:Piperidines / Q000032:analysis; D014230:Triazoles; D014508:Urea / Q000031:analogs & derivatives*
D000596:Amino Acids; D005449:Fluorenes; D010455:Peptides; D010880:Piperidines; D014230:Triazoles; C032727:piperidine; D014508:Urea; C074712:2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate