Solid-phase synthesis of the cyclic lipononadepsipeptide [N-Mst(Ser1), d-Ser4, L-Thr6, L-Asp8, L-Thr9]syringotoxin

Nuria Bayó; Jose C Jiménez; Luis Rivas; Ernesto Nicolás; Fernando Albericio

doi:10.1002/chem.200390126

Solid-phase synthesis of the cyclic lipononadepsipeptide [N-Mst(Ser1), d-Ser4, L-Thr6, L-Asp8, L-Thr9]syringotoxin

Chemistry. 2003 Mar 3;9(5):1096-103. doi: 10.1002/chem.200390126.

Authors

Nuria Bayó¹, Jose C Jiménez, Luis Rivas, Ernesto Nicolás, Fernando Albericio

Affiliation

¹ Department of Organic Chemistry, University of Barcelona, 08028 Barcelona, Spain.

PMID: 12596145
DOI: 10.1002/chem.200390126

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Anti-Infective Agents / chemical synthesis
Bacterial Toxins / chemical synthesis
Combinatorial Chemistry Techniques
Peptides, Cyclic / chemical synthesis*

Substances

Anti-Infective Agents
Bacterial Toxins
Peptides, Cyclic
syringotoxin B