A highly efficient azide-based protecting group for amines and alcohols.
The azide-based carbamate or carbonate protecting group (Azoc) shown above can be removed in less than 2 min under neutral conditions using trimethyl or tributyl phosphine as well as polymer-bound triphenyl phosphine. It was shown to be orthogonal to Fmoc and Mtt for peptide synthesis and to afford beta-glycoside with a 2-aminoglucosyl donor by virtue of the neighboring group participation.
Pothukanuri
Srinivasu
S
Institut de Science et Ingénierie Supramoléculaires, Université Louis Pasteur - CNRS, 8 allée Gaspard Monge, 67000 Strasbourg, France.
Winssinger
Nicolas
N
D000438:Alcohols / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis
D000438:Alcohols; D000588:Amines; D001386:Azides; D010455:Peptides