Improved solid-phase peptide synthesis method utilizing alpha-azide-protected amino acids.
[structure: see text]. Pure alpha-azido acids were prepared using an efficient diazo transfer method followed by buffered workup. These building blocks were used to prepare small peptides on Wang resin by two approaches. Peptides prone to diketopiperazine formation were prepared in good yields by coupling acids to resin bound iminophosphoranes during Fmoc-Wang synthesis. The iminophosphoranes can also be hydrolyzed under neutral conditions to provide unprotected amines ready for further coupling.
Lundquist
J T
JT
Division of Discovery Chemistry, Wyeth-Ayerst Research, 145 King of Prussia Road, Radnor, Pennsylvania 19087, USA.
Pelletier
J C
JC
D000596:Amino Acids / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D010455:Peptides / Q000138:chemical synthesis*
D000596:Amino Acids; D001386:Azides; D010455:Peptides