TY - JOUR
T1 - Direct Peptide Cyclization and One-Pot Modification Using the MeDbz Linker
AU - Gless, Bengt Herbert
AU - Olsen, Christian Adam
PY - 2018/9/7
Y1 - 2018/9/7
N2 - The one-pot synthesis and modification of cyclic peptides through a self-cleaving on-resin protocol is described. We apply Dawson's MeDbz linker to achieve direct intramolecular peptide cyclization by thioesterification followed by S → N acyl shift. This native chemical ligation approach requires no activating additive and allows direct modification of the crude cyclic peptides in one-pot. The strategy was applied to synthesize 5 cyclic peptide natural products of varying ring size. Finally, one-pot modifications include desulfurization, fluorophore conjugation, and intramolecular disulfide formation.
AB - The one-pot synthesis and modification of cyclic peptides through a self-cleaving on-resin protocol is described. We apply Dawson's MeDbz linker to achieve direct intramolecular peptide cyclization by thioesterification followed by S → N acyl shift. This native chemical ligation approach requires no activating additive and allows direct modification of the crude cyclic peptides in one-pot. The strategy was applied to synthesize 5 cyclic peptide natural products of varying ring size. Finally, one-pot modifications include desulfurization, fluorophore conjugation, and intramolecular disulfide formation.
U2 - 10.1021/acs.joc.8b01237
DO - 10.1021/acs.joc.8b01237
M3 - Letter
C2 - 30079722
SN - 0022-3263
VL - 83
SP - 10525
EP - 10534
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 17
ER -