Solid-phase synthesis and bioactivity evaluation of cherimolacyclopeptide E.
J Pept Sci
; 27(6): e3308, 2021 Jun.
Article
in En
| MEDLINE
| ID: mdl-33586251
ABSTRACT
Cherimolacylopeptide E (1) is a cyclic hexapeptide isolated from the seeds of Annona cherimola. Peptide 1 reportedly exhibits potent cytotoxicity against KB cells (IC50 0.017 µM). To confirm the structure and bioactivity of 1, we conducted a total synthesis of its proposed structure. The synthesis was accomplished via solid-phase peptide elongation and macrocyclization by employing Fmoc/OAll-protected amino acids on 2-Cl-trityl resin. NMR analysis revealed that synthetic 1 exists in two conformations in pyridine-d5 . As the spectroscopic data of the major conformer of synthetic 1 were consistent with those of natural 1, the structure of cherimolacyclopeptide E was confirmed to be 1. However, our synthetic 1 exhibited low cytotoxicity against KB cells (IC50 > 100 µM). In contrast to previously-reported findings, our synthetic 1 exhibited little antibacterial activity against Escherichia coli.
Key words
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Peptides, Cyclic
/
Annona
/
Solid-Phase Synthesis Techniques
Limits:
Humans
Language:
En
Journal:
J Pept Sci
Journal subject:
BIOQUIMICA
Year:
2021
Document type:
Article
Affiliation country:
Japan