Design and synthesis of a macrosphelide A-biotin chimera

The rational design and synthesis of a biochemical probe of natural (+)-macrosphelide A, a potent cell-cell adhesion inhibitor, was completed to aid in the identification of its biological target. The key features of the synthesis include: (1) an efficient synthesis of the macrosphelide core structu...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2014-09, Vol.12 (36), p.7127-7135
Main Authors: Yun, Hwayoung, Sim, Jaehoon, An, Hongchan, Lee, Jeeyeon, Lee, Hun Seok, Shin, Young Kee, Paek, Seung-Mann, Suh, Young-Ger
Format: Article
Language:English
Subjects:
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
Biotin - chemistry
Cell Adhesion - drug effects
Drug Design
Heterocyclic Compounds - chemical synthesis
Heterocyclic Compounds - chemistry
Heterocyclic Compounds - pharmacology
Molecular Structure
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Summary:The rational design and synthesis of a biochemical probe of natural (+)-macrosphelide A, a potent cell-cell adhesion inhibitor, was completed to aid in the identification of its biological target. The key features of the synthesis include: (1) an efficient synthesis of the macrosphelide core structure using Yamaguchi-Hirao alkynylation, (2) a cross metathesis to connect a linker unit to the allyl-macrosphelide and (3) coupling of the linker-bound macrosphelide A with a chemical biotin tag.
ISSN:1477-0520
1477-0539
DOI:10.1039/c4ob01028k