Stereoselective Total Synthesis of (-)-Thallusin for Bioactivity Profiling.
Angew Chem Int Ed Engl
; 61(39): e202206746, 2022 09 26.
Article
in En
| MEDLINE
| ID: mdl-35900916
ABSTRACT
Chemical mediators are key compounds for controlling symbiotic interactions in the environment. Here, we disclose a fully stereoselective total synthesis of the algae differentiation factor (-)-thallusin that utilizes sophisticated 6-endo-cyclization chemistry and effective late-stage sp2 -sp2 -couplings using non-toxic reagents. An EC50 of 4.8â
pM was determined by quantitative phenotype profiling in the green seaweed Ulva mutabilis (Chlorophyte), underscoring this potent mediator's enormous, pan-species bioactivity produced by symbiotic bacteria. SAR investigations indicate that (-)-thallusin triggers at least two different pathways in Ulva that may be separated by chemical editing of the mediator compound structure.
Key words
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Seaweed
/
Ulva
Language:
En
Journal:
Angew Chem Int Ed Engl
Year:
2022
Type:
Article
Affiliation country:
Germany