Solid-phase synthesis of the cyclic lipononadepsipeptide [N-Mst(Ser1), d-Ser4, L-Thr6, L-Asp8, L-Thr9]syringotoxin.
An optimized solid-phase strategy for the preparation of the cyclic lipononadepsipeptide [N-Mst(L-Ser1), D-Ser4, L-Thr6, L-Asp8, L-Thr9]syringotoxin is reported. The strategy is based on the use of a mild orthogonal protection scheme and the incorporation of the nonproteinogenic amino acid (Z)-Dhb into the peptide chain as the dipeptide Fmoc-Thr(tBu)-(Z)-Dhb-OH. The didehydrodipeptide was synthesized by a water-soluble carbodiimide-induced beta-elimination of a protected dipeptide containing a residue of Thr with its free hydroxy side chain unprotected.
Bayó
Nuria
N
Department of Organic Chemistry, University of Barcelona, 08028 Barcelona, Spain.
Jiménez
Jose C
JC
Rivas
Luis
L
Nicolás
Ernesto
E
Albericio
Fernando
F
D000890:Anti-Infective Agents / Q000138:chemical synthesis; D001427:Bacterial Toxins / Q000138:chemical synthesis; D020650:Combinatorial Chemistry Techniques; D010456:Peptides, Cyclic / Q000138:chemical synthesis*
D000890:Anti-Infective Agents; D001427:Bacterial Toxins; D010456:Peptides, Cyclic; C069036:syringotoxin B