Solid phase versus solution phase synthesis of heterocyclic macrocycles

Comparing a solution phase route to a solid phase route in the synthesis of the cytotoxic natural product urukthapelstatin A (Ustat A) confirmed that a solid phase method is superior. The solution phase approach was tedious and involved cyclization of a ridged heterocyclic precursor, while solid pha...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2013-01, Vol.18 (1), p.1111-1121
Main Authors: Kim, Seong Jong, McAlpine, Shelli R
Format: Article
Language:English
Subjects:
Cancer
Clinical trials
Cyclization
Cysteine - chemistry
cytotoxic
Cytotoxicity
Drugs
heterocycle
HIV
Human immunodeficiency virus
Leucine - analogs & derivatives
Leucine - chemical synthesis
macrocycle
Natural products
oxazole
Oxidation
Oxidation-Reduction
Peptides
Peptides, Cyclic - chemical synthesis
Serine - chemistry
solid phase peptide synthesis
Solid-Phase Synthesis Techniques
Solutions
telomestatin
thiazole
Thiazoles - chemical synthesis
urukthapelstatin A
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Summary:Comparing a solution phase route to a solid phase route in the synthesis of the cytotoxic natural product urukthapelstatin A (Ustat A) confirmed that a solid phase method is superior. The solution phase approach was tedious and involved cyclization of a ridged heterocyclic precursor, while solid phase allowed the rapid generation of a flexible linear peptide. Cyclization of the linear peptide was facile and subsequent generation of three oxazoles located within the structure of Ustat A proved relatively straightforward. Given the ease with which the oxazole Ustat A precursor is formed via our solid phase approach, this route is amenable to rapid analog synthesis.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules18011111