Synthesis and assignment of stereochemistry of the antibacterial cyclic peptide xenematide.
The synthesis of the antimicrobial cyclic peptide xenematide was accomplished by Fmoc solid phase peptide synthesis and the key esterification reaction was achieved using a modified Yamaguchi esterification. Comparison of the optical rotation and NMR data of the synthesized diastereomers to that of the natural product confirmed the structure of xenematide to be PA-L-[Thr-L-Trp-D-Trp-β-Ala]. (PA = phenylacetyl).
Hung
Kuo-yuan
KY
Department of Chemistry, The University of Auckland, 23 Symonds Street, Auckland, New Zealand.
Harris
Paul W R
PW
Heapy
Amanda M
AM
Brimble
Margaret A
MA
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry*; D047630:Depsipeptides / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000900:Anti-Bacterial Agents; D047630:Depsipeptides; C531271:xenematide