Convergent Synthesis and Anti-Pancreatic Cancer Cell Growth Activity of a Highly Branched Heptadecasaccharide from Carthamus tinctorius.
Angew Chem Int Ed Engl
; 61(32): e202202554, 2022 08 08.
Article
in En
| MEDLINE
| ID: mdl-35641432
ABSTRACT
Bioactive polysaccharides from natural resources target various biological processes and are increasingly used as potential target molecules for drug development. However, the accessibility of branched and long complex polysaccharide active domains with well-defined structures remains a major challenge. Herein we describe an efficient first total synthesis of a highly branched heptadecasaccharide moiety of the native bioactive galectin-3-targeting polysaccharide from Carthamus tinctorius L. as well as shorter fragments of the heptadecasaccharide. The key feature of the approach is that a photo-assisted convergent [6+4+7] one-pot coupling strategy enables rapid assembly of the heptadecasaccharide, whereby a photoremovable o-nitrobenzyl protecting group is used to generate the corresponding acceptor for glycosylation in situ upon ultraviolet radiation. Biological activity tests suggest that the heptadecasaccharide can target galectin-3 and inhibit pancreatic cancer cell growth.
Key words
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Carthamus tinctorius
/
Neoplasms
Language:
En
Journal:
Angew Chem Int Ed Engl
Year:
2022
Document type:
Article
Affiliation country: